City Winery Chicago Reviews

The City Winery concert venue in Chicago has an area as you enter where you can buy wines or hang out at the bar before a concert. The performance venue is intimate, with long tables where you can drink, dine and watch a show. I saw 80s pop star John Waite who still has a great voice and terrific performance style. For dinner, I had the very tender and tasty skirt steak with a burrata appetizer that included marinated tomatoes bathed in extra virgin olive oil and basil. That burrata was recommended by my server, Rhianna, who was a sheer delight! She was always smiling and so attentive....AND I learned she also is a singer/songwriter. City Winery is very lucky to have her on the team. My visit to this venue was one of the high points of my Chicago getaway. Note: There is also a City Winery without the concert venue on Chicago's Riverwalk. The one I went to on Randolph St. is near the financial district. So, after dark, this part of town is relatively quiet. If taking a cab, consider loading the Uber or Lyft app on your phone in advance, as there are no cabs to hail when the show lets out. I walked three blocks before finding one. But don't let that keep you from going! This is a rare jewel of a place!

Nice place to stop for an expensive glass of quality wine. Service was not a fine-oiled machine. Got to sit out and watch river activities on a beautiful day.

Attended a concert with friends. And yessss the setting is intimate...cramped. When the tables that were next to ours were being waited on we had to move to avoid being in the way of the servers. We didn't dine there, only had drinks. I may revisit, however I'm not excited about the space.

tables are too small for serving food, and you seat too close to next person. Music most of the time C and B bands

I’ve been to City Winery on many occasions but in this instance had the opportunity to share this great space with my dear father. We were there between lunch and dinner service pre-theatre and the staff could not have been more gracious and attentive. The servers are fluent in pairings and were patient with my dear Dad’s finicky palate. Everything was just delightful and I can’t wait to go back soon!

On Monday May 30, 2022 my wife and I arrived at City Winery for a late dinner and were greeted and seated by our server, Jennifer Y. We ordered a bottle of wine, the Cheese and Charcuterie Board and the Mushroom & Goat Cheese Risotto Balls, all of which were extremely delicious!! Jennifer was absolutely wonderful as we engaged in conversation and laughter all evening! It was a very pleasant evening after along day! Thank You Jennifer!! Beth & Todd

Came here tonight on my much needed day off for the movie screening "Gimme Danger" and we had a great time. Our server took care of us but was not over the top. They knew we wanted to enjoy the movie but were always visible so we could wave them down if we wanted something. Devin was awesome! It seemed like they were closing up but she told us to sit back, enjoy our drinks, and not rush which was awesome. She told us about upcoming shows and even classes they do there. We will definitely be back, thank you for the great service and great time.

We had a very enjoyable stop here on a sunny Friday -- great people watching, boats of all sizes going by, police on bikes, adults on skates, dogs on leashes. We sat out along the sidewalk for a drink while waiting for a table & then enjoyed a light dinner. Would definitely come again.

The music venue is great. Not a bad seat in the house. The appetizers were just ok so eat before you go.

First time at CW and we will be back. We were invited by friends who have been there before and wanted to see a concert, Very cool venue both in the restaurant which we peeked into and in the concert area. We arrived about 1-1/2 hrs before the performance time and shared some wines and starters. We just purchased carafes of the house wines which were good enough. Bottle prices were pretty high, IMHO. We shared burrata, tomatoes and toast and a charcuterie plate. Nice selections and the burrata was also good (needed a few more pieces of toast on both plates for 4 people however). I had braised duck tacos which were very tasty. Hubby had the linguine and clams and he said it was terrific. One friend had a flatbread and the other had a farro bowl and they enjoyed them. Only one person had dessert - cheesecake - but every crumb was gone. Nice waitstaff too.

Don't expect any personal space when seeing a show here! Paid top dollar for a seat and couldn't get to it without swiping my rear end across a mans back and still almost tipping the tall table with my front. Couldn't even straighten my legs for fear of kicking the "neighbors". Food is good, overpriced though.

This is a good date night spot and for friends. I went for an Eric Roberson concert and it was wonderful.

Go there only for the view... The wine is served ice-cold, at the pump, with drops beading down the glass... The Coke in a can... Nothing to accompany it. Nonchalant service. Error on the bill. Our worst experience in Chicago

Dined here with a group of 4. I ordered the French toast and potatoes. Very good! The potatoes were colorful and yummy. Definitely recommend.

I had the pleasure of going to the City Winery - Chicago. I went to see The Average White Band. It was my first time at this venue and I didn’t know what to expect. I loved it! The food was fantastic, the venue was light and airy and the accustics were top notch, as well as the overall venue. I can’t wait to go again. It’s a great place for people visiting Chicago to go, as well as locals.

We went with a large group of 60+ for a party and it was great. Food was prime rib, oysters, shrimp, crab, a couple of pastas, veggies, some sort of rice thing...and it was all really good. Not one single item was average. Concert venue was table based so you could snack during it too. Might hold 400+ but that is stretching it. Perfect to Uber in and out as valet parking was around $16 I think. Very safe area too.

My wife and I stopped here on a beautiful night during an impromptu bar crawl while our daughters were attending a concert nearby. When we came in, the hostess greeted us nicely and we asked if we could sit outside. She said “Oh I don’t know. I will have to go check.” Keep in mind that there were maybe 4 of the 30 plus tables occupied out there. As far as I’m aware, she is still checking because she never came back while we were there 🤪 We waited a few minutes and someone else came by and asked if we needed anything. We told him we wanted to sit outside and he said “yeah, I think we can do that but it will be like ten minutes.” And he walked off. Eventually someone else came by and walked us to a table inside. We were one of only two tables taken inside and the atmosphere was as if we were interrupting a bar that had already closed. We ended up getting up to leave and what I presume was the manager asked if we needed something and we told him we wanted to sit outside. He made our cocktails and had someone walk us outside. The cocktails were mediocre and overpriced. Service outside was fine but nothing special. Apparently this is a chain of locations and we would hesitate to visit any of them if given the chance in the future

I can’t say enough about this beautiful restaurant! It was literally the whole package - super attentive staff, incredible food (the menu has a wide variety of choices, and the flavors are spot on and so clean), even the building itself and the rustic finishes contributed to what I would call a perfect experience! The show was engaging and I thought the whole space was well laid out for enjoying the music, the bar, the food, either together or separately. I also loved seeing the variety of ages in the audience and in the dining room, and I found myself wishing my whole family was there.

Overpriced, few choices, understaffed and just generally bad. The ONLY positive is the view -the river, the city, etc. We were here last year over Labor Day and it was lovely, now it is terrible.

City Winery is a well-organized and cozy place to see a good artist. Sound levels are good, and there are good places to sit...especially around the perimeter towards the stage. We think it's worth the visit.

Went for a Paula Cole concert and the setting was perfect: mid sized (less than 1000) and charming. Great acoustics and no bad seats in the place. Long tables and chairs to facilitate wining and dining. OK food and nice drinks. Highly recommend.

Great place to catch some live music. We went early and had dinner before the show. Food is good and reasonably priced. The only down side is the size of the tables, and the order process. We went with another couple, and there really wasn't room for our food on the table. Also, the tables were very close together and a little cramped. I think it is pandemic related, but all ordering is on a mobile app. You also had to pay every time you ordered, so we ended up with 5 or 6 charges on our card. Appetizers, meal, dessert, and multiple drinks during the show. All separate charges. Also, not that convenient to pull out your phone and order during the concert. I hope this process changes after the pandemic. I love the intimacy of the venue, and sound was excellent. Overall we had a great time.

Book some tickets for your favorite small venue artists. I've seen Rickie Lee Jones, Graham Parker, World Party, Joan Armatrading, Ian Hunter, Richard Thompson, Lucinda Williams and many other artists. The wine selection is superb and the food is quite good.

Let me start off by giving kudos to the servers and bussers that work in such tight conditions, you guys rock. I went here to see Arsenio Hall and he did not disappoint. This is a beautiful place and the staff is friendly. Now for the bad. It's VERY VERY tight seating arrangements. Pick VIP area if that concerns you. It's a little more roomy. My other complaint was the microphone kept going in and out during the opening act and nobody fixed it for the headliner so it did the same for him. That was very unprofessional in my opinion. Other than that great show. I would come here again.

We went here for the Jean-Luc Ponty show, and had seats at the side of the stage. We had an excellent view and the show was outstanding. Our server worked very hard and was very friendly. He and Jean-Luc are the reasons that this is a 4 star and not a 3. Seating at the tables is shoulder to shoulder crowded. I had the very end seat and felt blessed (I think we had some man-spreaders at our table). We ordered Ancho-rubbed Octopus ($15) and Mushroom Flatbread ($16). The octopus was charred and good, the flatbread was merely ok. During the evening we had a bottle of CW 2015 West Loop Red ($33) and later a bottle of CW West Loop White ($24). The separate charges for Food Excise Tax ($3.57) and Alcohol Excise Tax ($6.56) were high. I also felt the portion sizes on the food were small for the price and that the quality of the wine did not stand up to the price. Overall, food and beverage for 2 people including tip was $114. I'm not sure what the tickets were as they were a gift from my husband to me. This is the kind of venue that attracts many baby-boomers that want to show off. We were seated across from a couple that when we started discussing Jean-Luc's catalog, launched into a litany of all the "great" musicians they had seen. As the woman drank and drank, she started regaling us with stories of the musicians she had slept with including two from major '80's bands, and that she couldn't even remember the guys' names. Hmmmmmm.... I wonder if she is still married to that second husband of hers that she was with that night? This venue is way out of the main part of the City. We took the train and thought it would be a short walk. It wasn't. Inconvenient if you are staying on The Magnificent Mile. It would have to be an amazing musician performing there for me to go back. Great music but everything else was pretty mediocre.

My wife and I bought tickets for a concert and decided to have dinner beforehand. Wonderful industrial feel to the building. Huge wine selection. Great menu choices and prices. Great ticket prices and great place to watch a show. Looks like a wide variety of top entertainers coming up. Will definitely come back

Great service - Christine. The place is very busy - both inside, outside, and all around. We were placed at a table overlooking the river which was nice. Great for watching the boats in the river, the yachts and their parties, and the people on the Riverwalk. The wine is just ok. I had the mushroom risotto which was very tasty and my husband had the salmon which was cooked perfectly. Nice experience.

Had gotten tickets to see Keb Mo, sold out show and made a long weekend out of that! Was so excited and experience matched my excitement. Starting with the adorable greeter who walked us to our seats at the bar we thoroughly enjoyed the entire evening. Bartenders were fabulous, and, had to get the duck tacos again. Favorite there. Bartender, Chris, we really patient with me (pretty picky drinker), thanks, Chris! Concert was amazing, just love you Keb Mo! Seats were great. Have been here 6+ times and still trying to find my favorite seats.... but all are good! Will be back in July to see the Bacon Brothers.

I was at the City Winery (Randolph Location) on Saturday April 20th with a friend for the Lala Hathaway Concert. We had excellent seats for the 9:30 pm show. When we arrived the waitress asked for a credit card for dinner and drinks, to which I gladly offered. However, that was last time she came to our table to check on us. I wanted a 2nd glass of wine, but never attended to. Service was HORRIBLE!!! I am a regular at City Winery, at least 3 -4 times per year. This is not the 1st time I complained. It has become apparent to me City Winery does not care how they treat their customer, as long as we continue to purchase tickets. I wish Chicago had another venue that catered to my taste of music. I would drop city winery like a Bad Habit!!!

I had purchased tickets for a show this August, but due to circumstances was not able to attend. A classmate of mine was going in my place and would use the tickets. I was somewhat concerned about this, particularly since they used names for the reservations. However, I was able to reassign the tickets to my friend, and they were able to attend with NO problems whatsoever! In fact, the seats were there and reserved as planned. And the show, Rachelle Farrell, was exceptional I have been told! I look forward to attending this new venue in Chicago, and also having a few beverages at their other location on the Chicago River.

We were in Chicago to see the kids. We were looking for a place to enjoy the family and food and wine. We found it. City Winery on Randolph. Buck was our waiter. Helped explain the menu and the portion size. We loved the Burrata appetizer. Don’t forget the wine. They make their own. It’s a winery. I had the linguine with clams. Wonderful! The wife had the scallops. She didn’t want to give me a taste. I understand, they were great. Our son had the duck tacos. Had to reach across the table to get a taste. Don’t forget the wine! Buck was attentive and checked with us often. Our friend at The Real Chicago recommended this restaurant and he was definitely right. Get out some night and enjoy yourself.

We always enjoy our dining experience at City Winery. Great food (burgers are awesome) & drinks, a wonderful atmosphere and excellent service. Look forward to checking out the music venue soon.

Going to see Maysa was an absolute delight! Drinks and a flat bread were okay. Deviled eggs horrible! The venue sound was great and the show was great, however it is a cramped, uncomfortable mess. The small tables are positioned in an uncomfortable arrangement to accommodate true enjoyment. Staff were kind enough, but intrusive during the performance. Loving the show is not enough! Now the food: just a plain old cheese burger would have been suffice, please and thank you! Trying to be hip and eclectic failed. Our group of ten did not enjoy our meals in the restaurant. Trying to be too hip can be unhip! The waiter was outstanding and that should be noted. I will probably go to another show, but no pre-show appetizers certainly no dinner in the restaurant. One more point, fire place was nice, but the smoke was a distraction during dinner! I suggest they deep six the devil eggs and add a couple plain fair to offset the awful the BBQ pulled lamb. Go for the show, expect table discomfort and eat somewhere other than City Winery.

Evan was so knowledgeable and we had so much fun. i’d recommend the tour for anyone!! the wine was also incredible. 10/10 recommend

Sampled 2 different glasses - Merlot and Pinot Noir and both were good. Merlot was slightly better. Nice bar for sipping and chatting.

I bought 2 tickets for my friend and I to attend the ABBA brunch on 2/18/24. The entire experience, from start to finish, was very below par. It started at 12:00. We arrive around 11:45. We were shown to our seat. I had chosen the buffet option when I purchased the tickets. The line was extremely long, and we waited about 15 minutes. It wouldn't have been an issue if the wait was only due to the large crowd. But once we finally arrived at the food, there were several issues. People had to wait for plates to be brought out. The eggs had run out and people were waiting for those. They were completely out of sausage. The fruit tray in the lobby was completely empty. We took small portions of what was left. None of the food was good. The eggs, when they finally arrived, were runny, the pasta had no flavor, nothing was homemade. The waffles and biscuits were not made in house. The muffins were dry, and not fresh at all. We were seated back at our table around 12:05. By the time we left at about 12:55, the waitress still had not approached our table asking for our drink order. We tried to go to the lobby at one point to order a drink from the bar, but it wasn't open. There must have been staffing issues at the bar too, because we noticed that once she took an order, it took quite a while for her to return with drinks. We were never once acknowledged, or even told that she would be right back. It's like we weren't even there. Also, the band was not that great. I expected more flair and enthusiasm from the female lead singers, but they fell flat. Not much expression or movement to their act. The entire experience was very disappointing. We left before it was over because we didn't want to waste even more time waiting for the. valet. Its' really a shame, because City Winery is a pretty cool venue. I have been there man times before for other shows. Service always seems to be a little slow, but the experience has never been this bad. I hope they get their staffing issues figured out. I won't return for an event like this again.

We sat along the counter facing the river, enjoying the wine and beer while watching the boats. The food choices were limited but tasty, and the scene beats the heck out of staring at walls.

Family in from Belgium for the holidays. After Christmas brunch we headed downtown for the show. We had some nash and a few drinks & saw a fantastic show. Some of the jokes we may not have fully appreciated but a great show none the less. Would def go again next year!!

On or about April 20 or April 27th, 2019, my husband and I went to see Herb Alpert and Lani Hall at the City Winery Chicago. We arrived about 3 hours early ( as I thought the show began at 6, which it actually started at 8 p.m.). This was fine as we were able to get about a mile and a half of walking around the area in after having dinner there. Dinner for us was an Impossible burger for me and beef burger for my husband, which we really enjoyed. Unreal how the Impossible burger looked and tasted like a meat burger. The buns and fresh cut fries were great as well - except they did not give us enough fries. The chairs inside the venue hall were just a little to hard though. If padding could be added or other types of more comfy chairs, I would rate it a 5. But it is a very nice venue and the burgers were great and we will be back for both the food and concerts.

Go here! It's such an awesome vibe and you get excellent service! We had James and he was so helpful and accommodated all of our needs!

Ticket prices very high now because of social distancing, I assume. Masks, temp check, personal questions and contact tracing even if vaccinated. Could have been handled much better and friendlier. Ordering only by cell phone. Mediocre wines, 4-6 oz pour at best. Sliders were very good. Love this venue but WAY too loud this time - like eardrum piercing loud - and I like loud. Ask for ear plugs, my ears are still ringing.

Hands down the best place to see a show, have great wine and amazing food in Chicago. The staff is unbelievable!! Mad love

1st timer here (not the last)... I was greeted from when I first entered warmly...look of the place is very artistic... Food is tasty and filling... Good acoustics... Good customer service!... Attended the Betty Lavette show... Will be back ‼️🌚🍷

Don't pass up attending the performance of your favorite band if they are booked at the City Winery!! You will NOT be disappointed!

While billing itself as a winery and restaurant, it is really an entertainment venue. Unfortunately, four of us went to taste wine and have dinner. Flights for tasting were not available for dinner...only happy hour. Also, there were no wine pairings recommended for the limited menu selection. Though reservations had been made10 days prior and we showed up 5 minutes early, we were seated in what could only be described as a bar and waiting area for the entertainment room. We were told that's the way it was leading one to wonder why would we bother with a reservation. Also, our waitress disappeared after we ordered an additional item and wasn't seen till it was time for the check. The top of the menu rec ommends 2-3 items per person for sharing. NOT TRUE! Our party of four would have done well with 4-5 items.

My husband and I had a wonderful evening enjoying Goapele in concert at City Winery. The setting is intimate so all the seats are good. Service, food & drinks were all good. We look forward to going back for other concerts.

I had been to hear music once before at City WInery but it was a very informal event so I sat very close to the stage. This time a friend bought tickets for a concert and fortunately we sat to the far of one side on the first level, the room has a slightly upper tier section in the back. I was surprised by how tightly packed everyone is. I will say that I thought the servers managed incredibly well in what has to be very difficult conditions. They were on top of things and made checking out very easy. My suggestion is to be very picky about where you sit and pay up if you are on the fence. I really was shocked by how tightly packed we were at this table and it got me a little nervous, fortunately we weren't tightly packed in the middle. I don't think I would have been able to handle sitting there. I did not buy the tickets so I don't know what the price options were. But my suggestion is to pay up if you can, it will just elevate your experience immensely. I don't go to concerts much at all so I think in retrospect I would have paid up for better seats but I am happy that I was right by the metal divider. The space is very intimate and the acoustics are decent and checking in and seating was very easy. We got dinner at another venue and then arrived about 10 minutes before the show, easy peasy and I am happy that we did. The table was far too small to have gotten any food. The wine list was really diverse, well-chosen and interesting and you can see that much thought was given to the choices. So many places in Chicago have the same big brand names at high prices. My whole experience was great and I would definitely come back. As I said above, I would scrutinize the seating chart and be very picky next time and pay up to have a more comfortable, not-crammed in seat.

I'm a big fan of the original in NYC. I've been the Chicago one multiple times to dine and for charity events. I love the space - very cool atmosphere. A great place to take out of town guests. A lot of the menu is shareable food, so be forewarned. The only downside to this place is the lack of it's wine flights - I really think they are missing out an opportunity. The servers are very knowledgeable of not only the in-house wines but the others the restaurant carries as well. Its a place that is good for a drinks and apps as well as a full dinner. All I have left to do here is actually see a show.

We went to a comedy show at City Winery and really enjoyed ourselves. The menu had some nice options for food and drink. It's a smaller venue which makes it very comfortable.

Forced to make a 1 reservation due to the in availability of other times to dine. When we arrived, there were only a few people sitting at the bar and no other dining patrons to be seen. Fortunately, we were seated quickly and ordered promptly but had to wait over 20 minutes for the arrival of our first food. As others have lamented, portion sizes were less than modest. Food quality was acceptable. My dining partner had crab cakes Benedict while I had chicken and waffles. Chicken portions were very miniscule. Waffle was dense as opposed to the expected airiness of a Belgian waffle. House white wine, at $33 for 1/2 hour, was extremely pricey although of average quality. Will probably try once more when a more complete menu is available.

This is a nice, intimate venue for a concert. We say Rodriguez play. The environment is nice, warm and intimate. The food is average, service average too (although, I can imagine that it is difficult to serve during a concert).

I saw Living Colour, and they were just as amazing and strong today as they were when they first hit the scene more than 20 years ago. But - that doesn't tell you about the place (the sound was great - always very loud with this band, so bring hearing protection). First off, I was running late, and parking in this trendy neighborhood can be tricky. Luckily, the venue has valet parking, and these guys are quick! Yeah, it was $13, but I'm used to going to City Winery in NY, where it costs $15 to get through the tunnel, so this is a relative bargain. And it got me inside before the show began. One thing I don't like is the large lobby when you enter. It's unclear where you're supposed to go, and there's never been anyone near the door to ask. I went up to the counter and it turned out the stage was to the left. Most all seats in front of the sound board here are good - I've been twice, and both times sat in that area. Service is spotty - it depends on the server. If they're new, they seem to have difficulty getting to everyone in their area twice. I had to ask another server to send ours over, and I saw him for the first time in the last third of the evening. But, other times, other servers, and it's perfect. All told, I love City Winery for shows, the food's usually quite good, but if you're not careful, it can add up to a $200+ evening after a pair of $40 tickets, valet parking, a couple of meals, a few drinks. All in all, go, enjoy the show, watch what you order if you have a tight budget, and you'll have a great night out!

We've attended 2 concerts here in both cases guests were uncomfortably squeezed into our seats and servers were trying to accommodate multiple tables spread all over and literally dozens of guests. I'm sure you can see a good show here, we didn't, but for the price it's a poor value...basically one large banquet room. It's greed in my opinion. Regarding the last show, Rodriguez...an awful show, worse, it was embarrassing for the man. The man is ill, no two ways about it, we and the audience around us were horrified, he played maybe 8 songs, barely got through them, couldn't walk to the stage, appeared he was blind as he couldn't find his water and so on. I'll leave it at that. The venue had to know what condition he was in and still allowed the show to go on. After drinks the night cost us $500 for 4. Worse...they put him on at their DC club the next week. Really poor ownership/mgmt here. Won't return.

I was excited for my front row seat to Al Di Meola. Upon arrival my chair was my (bizarrely) facing the wrong wall with no possible view. Naturally I move to rotate the chair around to see the stage. Within the first split second (I was still standing up!) a large service woman is already reprimanding me "NO, you cannot have your legs in the aisle". Wow, this was within the first 30 seconds of arriving and I wasn't even done rotating my chair. Does she want me to watch the wall instead? It felt very rude. I quietly prayed to never need to see that rude server again. Lo and behold no service was available for the next hour. I was really hoping for a drink so eventually I had to walk to a non-service employee to ask how to get service and she came. That was my bad experience. In sum: The front seating arrangement is insultingly stupid and the service was pathetic.

This is a great spot on the River Walk to sit and have a glass of wine and a snack and people watch. Service is good here and they have a nice selection as well as their own line of wine. Very pleasant spot under the MIchigan/Wacker Street Corner

Went with friends to enjoy a boat trip to City Winery for a celebration. We had a great time, it was so cool to dock next to City Winery and enjoy the spirits! An amazing evening and although you are in the middle of the city, you feel like you are on vacation. We had a great time watching all the folks on their boats, the foot traffic and just chillin on the water! I highly recommend it!

Please note that this is a review of the concert venue only, we didn't try any other portion of the restaurant. What you need to be aware of - I mean, what you really, *really* need to be aware of, is that some of the seating in this venue, including some of the most expensive seating , is absolutely awful, and guarantees that you will not enjoy the performance. The problems is this: the seating layout consists of tables that radiate out from the stage area like spokes from the hub of a wheel, there are *no* seats in the main seating area that directly face the stage. This arrangement means that in the rows toward the either side of the stage, half of seats in each of these of rows have *no* direct view of the stage at all if you are facing the table. Instead, your sight-line is instead directly toward the blank wall of the room - and the closer you are to the stage, the worse the problem. So in these these seats, if your chair is facing your table, the *only* way that you can see these act *at at* is to look over your shoulder. The obvious solution is to turn your chair 90° toward the stage. Only good luck with that! The chairs are packed so tightly side to side along the table that there is - literally - less than an inch of space between the chairs; you can't rotate the chairs at all, your only viable option is to pull the chair out entirely and turn it around once the act has started, which of course means that your feet are in the narrow walkway between the tables which is the only access for the servers. In addition, our party of two were seated side by side with both of us facing the wall, so we we didn't even have the option of trading places so each of us had marginally acceptable seating for half the act . Instead, we spent dinner looking across the table at another couple - and the tables about 20 inches wide, which means that you're going to be having an intimate dinner with strangers whether you want to or not. Then, there is the wine. OMG. For a place that has "wine" in its name, the house wines are beyond disappointing and far into the realm of the abysmal - just don't even think about trying, instead look across to the other side of the menu and order a glass of something created by someone who has some remote idea what they're doing. Otherwise, you will be paying $14 a glass for a miserly pour of nearly undrinkable red liquid. If there is a bright spot, it was the food: the mushroom flatbread was very good, as was a the *small* dessert , and service was fast and attentive. But nothing - absolutely nothing - could possibly compensate for the seating. I would say "contempt" would be a pretty good term for the attitude toward their patrons expressed by the creators of the seating arrangement, and I can't imagine any act good enough to compensate for the infuriating disappointment of paying premium prices for just plain unacceptably bad seats.

This was a great experience and vibe. I enjoyed I enjoyed the wine and th salmon. Just delicious eats! If you visit make sure to try the Cab!

If you can afford it, a good venue for music, food, and wine. Not cheap--but reasonable value. We had pan seared chicken, braised short ribs, and a creamy swiss chard dish...along with CW-made malbec, which was quite good. For 3 of us drinking/dining, tab was $155 before tip (no dessert). That didn't include concert tix. I can't say I'd spend that much just for the food, but it was worth it as an accompaniment to a wonderful concert (Funkadesi).

Well, if it is fine food, this place works as well. Gazpacho hit the spot on this perfect summer afternoon with a great server and lead into a main course of Cavatappi Pesto.A glass of Pinot Gris to wash it down and a delightful way to enjoy lunch!!

Went with our 3yo for dinner and the chef was so accommodating! Everything tasted exquisite and the staff were very friendly. The show after dinner was just as delicious and can't be beat for a fun night out.

We visited to watch the average white band. The concert wad superb as place is very intimate. Great bar area as well with superb wines. Fabulous place. We also met the band

City Winery is a great place to relax and enjoy the view of the river! It was very warm the day we were there, but still enjoyed the atmosphere very much. Wine and appetizers were both delicious. Wait staff was very helpful and attentive. We would definitely go back!

I won tickets to see Micky Dolenz at City Winery. Thank you MeTVFM, 87.7! Although I had been curious about this place, I'd never been there. My 15-year-old daughter wanted to go too, so what the heck. We did it. We took the train into the city, grabbed an Uber at the train station, and a few minutes later we were there. City Winery is located in a fine part of the city, just west of The Loop. I don't know about parking because of how we traveled. We had an appetizer and flatbread pizzas. Those were all very good. Our waiter tried to tell us that all of the dishes on the menu were shareable, but I don't think that is true. How are you supposed to share a cheeseburger? Some of the dishes are shareable, definitely. But not all of them. Others on TripAdvisor complain about the concert seating. We had no problem at all, and I don't see what the complaining is about. The venue is intimate, and if you are not facing the stage, all you have to do is turn your seat. That's not tricky. City Winery probably isn't a great place to take little kids, but it was perfectly fine for a teen. As the performance wound down, the wait staff did a great job of delivering the checks and collecting payment. They have a very good system for that. All in all, this was an excellent experience. and I look forward to returning.

We have visited this venue multiple times, it is a great place to see a show. The only issue I have is the cost of a meal or a drink. An old fashion is $12.00 each and the beer we had was $8.00 a bottle, that is $48.00 a six pack. I understand profit margins, but I feel the costs of the food and drinks are high, even for Chicago. Great venue, but eat before you come.

I came here to see Basia’s concert. It was great. This venue is unique since you dine when listening and you may share tables with strangers which is quite cool. But it might be s disaster as well.

Had a great time with out of state friends. The venue attracts all ages of jazz aficionados so as the older set we fit right in.

We stopped at this restaurant when we saw the word 'winery'. We had walked from downtown and were thinking of going another 2 miles when we opened their door. Although they weren't doing wine tasting that day, the greeter told us they had wine and that's kind of the same thing! She was so sweet, we decided to rest our feet and enjoy their hospitality. While we sat at the bar, I tried first a South African Pinot Gris but liked the Winery's own much better. My husband enjoyed the 'mystery' cab from Rutherford. While we were there, we spoke with one of their servers, Stephanie, who went out of her way to recommend some nearby restaurants. We had looked at Yelp and TA, but local hints are always good. She steered us to some lovely new places but more importantly, she was just so darn nice to talk to. Chris at the bar was also friendly. We're glad we stopped by!

Great place to see a show. Nice venue. Clean. Good location. Dinner menu needs to be revamped. Beer selection is bad. They sometimes put out a commemorative wine for the artist. That’s cool.

Family and I went for drinks. They messed up our order. The guy admitted he forgot to put the order in. He then placed the order and charged me. I was shocked they had me wait a half hour for one slice of cheesecake. I told the cashier I was surprised he charged me $12 for cake. He said he couldn’t comp it but offered a drink. The other staff raise two fists at me. He made comments to another staff. I’ll never return.

I went there for a private comedy show and it was great! Close enough to walk from Metra and valet is available. Staff was great and the venue space was amazing. Spacious and comfortable, even with 300 guests.

First-timer here last night to see the great Christian Scott. It's a shame about this place - it has a lot of great shows here and the setting is pretty good but the service last night was bad and dampened the experience. It started with confusing communications from the venue regarding "doors open" time that was incorrect and I think was confused with the restaurant opening. Further, it is confusing as to your dining options if you are attending the show. The host at the door provided an explanation that I just ignored because I could not understand the explanation. We opted for the dining room before the show. It took 10 to 12 minutes to be recognized by any staff once seated in a room that was fairly-empty at the time. I had to tell our waiter that we were attending the show and we had to be mindful of the time. He told us he would keep an eye on all that. He did not. We had to track him down at every step of the meal and had to hastily get the bill to pay to close before going in to the venue for the show without receiving our entree. He had our cold entrees delivered to our seats in the crowded venue where it was difficult to do little else but enjoy the show. We never did get offered drink service in the venue. The mens' washroom was dirty and had the world's noisiest HVAC unit that sounded like it was ready for takeoff. Oh, the food we did have was good but pricey. Thank God Christian Scoot and the band was worth the otherwise poor experience. I'll be back for another good show but I won't be eating here pre-show.

The line-up of entertainers has something for every musical taste. The music venue is intimate. You may dine at your music venue seats or in the adjacent restaurant. The seasonal menu has interesting choices. The hors d'oeuvres were terrific. The lamb sandwich was delicious. Servers work hard to unobtrusively respond to food and drink orders during the concert. It easier to arrive well before the concert so that you can dine comfortably and then fully enjoy the concert with a glass of wine.

We had a great night at the Jim Brickman show The food was great I would highly recommend the king Poe cauliflower, I know it doesn't sound very good but let me tell you it was awesome. The show was great and the staff friendly

LOVE City Winery. It’s intimacy, delicious wines and great sound system makes a great night out destination. Saw Average White Band and Basia there and thoroughly enjoyed both evenings. The seating is a little tight but the performances make up for the closeness with strangers. Highly recommend a visit here.

Definitely a place to visit when you come to Chicago, it is. An easy place to find, parking not too tough , good neighborhood

I have been to the performance venue twice. It is intimate, which is nice for feeling part of the show. However, the seating is at tables that run perpendicular to the stage and it is so tight I worry that the crowd would never get out in an emergency. If you tend to feel claustrophobic get something in the back or near the side exit. If you intend to get food, arrive in plenty of time because as the place fills up it becomes almost impossible to make and get your orders (especially if you are sharing a table with strangers that are arriving at different times).

We saw one of our favourite live bands here in late 2016. They'd previously played a different north side music pub (which serves pizza and other noshes) for several years every time they came through town. This was the first time any of us, I think, were at the City Winery for a concert. We booked tickets early and got a table. When we arrived it seemed more white-linen restaurant then club/venue. This proved right, and expensive. We ended up feeling almost required to order food. People were talking and eating during the performance, so much so by a large table nearby, that we sometimes were quite distracted from what we'd paid to see and hear — the band. We did not feel comfortable here and would not return even if the same band books with them again. It's just not a performance first place. I would recommend this as a place for locals to hang out and enjoy wine in their bar or, for those who like a sit down dinner while talking and listening to musical artists.

I treated my husband for his Birthday to the Spyro Gyra 50th Anniversary Tour, Oct. 11th. This was the worse experience ever; the place was jammed packed and very uncomfortable; we felt like sardines in a can. The acoustics were awful. We will never visit this venue again in life :) additionally, we were overcharged for the tickets because there are various 3rd party sellers who are able to access their ticket site.

We went to City Winery with friends and had a great meal and the service was fabulous! We would definitely recommend this restaurant!!

We were there on a really warm September late afternoon. I found the maitre'd to be a little snotty. It was very, very busy and there was a 45 minute wait for a table. So we sat on the benches in front along the river. But to our surprise, a table became available after 20 minutes! The menu is very limited. The wine list is okay. The wine was better than then food. The food was very small portions.

We came from out of town for a concert with the Irish band High Kings. Would come back anytime for an act we like. The venue is top notch - cozy atmosphere, food choices and quality are way above what we expected. Extensive beer and wine selection. Clean space, we'll run. We had a fun server with Tia - very efficient and helpful. We had a small wine tasting before the show at the wine counter - extra bonus! The Winery should also be a good place to visit without an act going on - there is a large restaurant space and a beer garden. The only thing we missed, from having been to a similar space in DC, would be a dance space to get active with the music.

Family wedding at the winery. Live entertainment, excellent wine, beautiful old building with tons of interesting features. Wedding for 150 people served New York steak that you could cut with a fork, cooked to perfection and served piping hot. That's a tough act to follow.

Went to this location for a business cocktail type event. We tried to sit outside but we were rained out but location was great about relocating us. Drinks were excellent and plentiful. Food was upscale and fun for a winery location. Would recommend going again. Wish we could have spent more time in the outdoor courtyard seating area as it looked very nice!

I was here for a M.Mcdermott concert (which was awesome). The people who work here were so nice. Is a little cramped.

They didn't have much in a choice of wines, and I didn't find one that I enjoyed. But we really did enjoy sitting on the steps and watching the river traffic on a beautiful day.

The person that set up the seating for their concerts is a genius. Take the worst seats in the place, call them VIP, and charge the highest price for them. These VIP seats are the furthest from the stage. There is nothing VIP about them. Food was ok, at best. Service was slow.

My husband and I went here last year to see Amel Larrieux in concert. Amel is awesome in any venue, but it's the smaller ones, such as City Winery, in which I prefer to see her perform. The concert space isn't particularly big, but it's not too cramped; however, the house was sold out, and there were a lot of people in the room, and did have to sit at the table with a few other people. The spaces in between the tables get a little tight toward the front when there are people sitting at every table, including the table where my husband and I chose to sit, which was on the left side of the stage. The staff were very accommodating, though, and repositioned the table so that my husband and I could sit down comfortably. We were still able to see everything fairly well. Everyone seemed to be enjoying him or herself. The food was decent, though I can't exactly remember what we had at that time. Servers were attentive and brought us everything we ordered. We valet parking, which is the better bet than trying to find parking elsewhere. Tickets were also very affordable. All-in-all, I would return here to see anyone in concert. It's a pretty decent venue for an intimate concert.

I wanted to order a cake on Friday night for Sunday party. I was told that the restaurant requires at least 72 hrs notice for this kind of cakes. When I explained the significance of the event being celebrated, Adam, the restaurant manager, went above and beyond to make it happen. Despite the fact that the restaurant was handling several weddings and pastry chef was extremely busy, he was able to convince her to squeeze in my order. Adam emailed me at 11 pm to let me know that he was able to accommodate my special request. If I could give 10 stars, I would.

The City Winery was an amazing venue to get together with friends and family. Atmosphere was amazing, service was spectacular, and the entertainment sensational. A must visit when in the city! I recommend The City Winery to everyone-locals or visitors!

This place is the perfect spot to enjoy a delicious meal, drink some good wine, and enjoy some good music! We had a wonderful evening!!

Martin Sexton concert. Lovely wine list, intimate setting. Good view of the stage from every vantage point. You will not be disappointed if you arrange to attend a concert here. Cool vibe all around.

Hubby and I enjoyed our concert experience. We had great seats. However, I noticed some of the seats were not that great so be cautious when selecting seats. Get there a little early to eat. Nice being able to order food before & during the show. Great service, too.

Third time here, always pay to be up front close to stage. Larry Carlton, Timothy B Schmit, and two days ago Layla Hathaway. Love love love her Joe Sample CD. Almost left because sound mix was basey and muffled most songs. Miserable seating had to lean almost out of my seat to keep people off of me. Bought end table seats for that purpose then asked to move off end of table row, while other end sitters were doing same thing. If I had complied I would have sat in the Amazon ladies lap. Suggestion, take one table off of end of each row, to provide humane seating. $78 dollars per seat to be miserable

We made a reservation last week on Open Table for last night at the City Winery. We show up there last night and they are surprised to see us, because they have a private event and the restaurant is not open to the public. Thanks to an AMAZING MANAGER, we were allow to have dinner anyway and see a great show. A big thank you again! We came from Montréal, Canada and totally appreciated this very nice friendly gesture.

The concert I saw was awesome, sound was spectacular. Food was very good. Burger was very tasty and sweet potato fries were so good. Only four stars because the seats were so tight together and hard wood was uncomfortable after a little bit of time. Literally there are four chairs around a table that is not as wide as the chairs. The chairs are stacked side to side with no room at all. I read reviews and knew this going in so I was prepared. I was 2 seats back from the front of the stage. Safety wise I felt pretty good. We walked to and from the concert from hotels across the interstate on a Thursday night. At 11pm there was still enough activity to feel comfortable.

My fam visited last weekend to see Anita Wilson. She was amazing, but the seats and tables leave very minimal room for eating. My advice - splurge an extra few bucks for VIP. Food was overpriced, but that's expected in the West loop.

I love this space...I frequent it often. They offer a variety of musical artistry, great food and beverage selections. It’s a real Winery...in the heart of the city. They offer tours...private events... Did I mention that the food is delicious and the Waite staff is stellar??? I’ve never had a negative nor disappointing experience at City Winery; it’s the best.

This was our first visit. Saw Boney James here. Loved the venue. It took a while to get seated. They were out of the two wines I tried to order. And the tables near the stage could not have been packed more closely together. I would not sit there again because it was so tight. I would sit toward the back where there appeared to be a little more space. I would be willing to a pay higher ticket price to sit close if the tables were spaced out. Despite those shortcomings, we enjoyed City Winery overall.

Having never visited City Winery, we ordered a tasting and tour package on-line and we were looking forward to it. Unfortunately, the email confirmation didn't reach me prior to the visit and my wife and I thought we would be turned down for the event. However, the good folks at City Winery demonstrated extraordinary customer service and graciously provided us with the tour and tasting anyway. As for the experience itself, Nick did an exceptional job with the tour and the wines were delicious. We appreciated the generous pours for the tastes and stuck around for a tasty meal afterwards. City Winery is on our radar screen now - we'll definitely be back!

My lady and I drove all the way from St Louis to Chicago expecting a wonderful evening of wine drinking and singing by Rachelle Ferrell with our Chicago family, but that was "not" the result.... 1.) The venue looks nice, but the seating for the performance had people practically sitting "on top" of each other and views to the stage were blocked by other people's heads (Poor seating). a.) Due to the cramped seating, waiters and waitresses were constantly brushing past you and interrupting any comfort that you may have had... 2.) I ordered a glass of Malbec wine, approximately $15, and it was the worst Malbec that I had ever tasted (very bitter). Although the cabernet sauvignon that I tried next was a lot better... $30+ for two glasses of wine (One bitter and one just okay) 3.) The performance by Rachelle Ferrell was absolutely terrible... I have experienced her singing many years ago and she was absolutely amazing... You could even tell that her band was unaware of her "soap-boxing" and "world views"... Everyone just wanted her to "SING"... a.) The sound quality in the venue didn't help either... Whoever the sound engineer was had the instrument sound up waaaay to loud and the singers mic waaaaay too low.... I was very disgusted with my entire visit to the Chicago City Winery... I would tell people to proceed at their own risk...

Are at City Winery before the Kurt Elling concert. My advice, eat and drink wine elsewhere. The wines and the food were not worth the price. The service experience was substandard as well, with empty promises and forgotten item requests. If you must eat, I suggest the kale Caesar. Beet soup and Swiss chard were fair, at best.

We gave our phone number ( +353-Ireland) and was told we would get a text in 25mins….time passed , plus a bit …no text came .I went back to the host and queried our reservation…to be told ..”it was an international number ..so text didn’t go “””… no apologies or attempt to make it better . Eventually we were seated and after some exchanges with “Donny” the manager we moved table ….food was ordered …40 minutes later , again after many queries it came out COLD and the quality was terrible . No attempt to follow up by Donny on our experience, and when paying the bill , I was asked about a tip …my only tip for Donny and this place ..is go back to school and lean how to deliver customer service ..and cut out the crap excuses …DO NOT WASTE YOUR TIME OR MONEY IN THIS PLACE ….It’s all fur coat and no knickers or style over substance #citywinerychicago @citywinerychicago

Lunch on a Sunday hoping for a go-to close by. Standout food item was whipped feta YUM. Salads and pizzas ok. Endless brunch items ok. Wine flight had one decent Pinot Noir others all lite. Chardonnay ordered separate lite. Confident our wine judgement is accurate.

What a great place for friends to meet up and enjoy time together...with great wine! I had the roasted chicken and my friend had the burger. Both were wonderful! The atmosphere was great, the service was good and the wine was amazing! Easy to make online reservations and parking was a breeze! I'll be back with my husband!

Went to see Tab Benoit at City Winery. The venue itself is great, very intimate and well run. The stage and acoustics was very well done. The food was pricy for very small portions and the plates we ordered were only average average at best. Of course they claim to be a winery but i'd skip their wine and just get cocktails. The wine is poor at best, but it seems that like Coopers hawk, they've discovered that making and labeling your own wine is a goldmine however it is worse than you can imagine and extremely expensive. We will most definitely go to concerts there again because of the atmosphere but will eat dinner at any of the great restaurant along Randolph and skip the $60 bottles of bad wine.

We loved seeing one of our favorite musicians but this was a very cramped venue. We were seated at long tables with other guests and the chairs were very close together. This is a little bit uncomfortable in times of a pandemic. Everyone was required to provide proof of vaccination But no one wore masks. The wine was very good and the food menu was quite creative. But I’m not sure I would go back because of how close the seating was

We really enjoy our afternoon at the city winery in Chicago! The music was great and the atmosphere was fantastic. Perfect place to hang out and watch the people of Chicago passing by!

One of the worst music venues I have ever been to!! There is no care or thought put into this place at all and it shows!! Seating is AWFUL who the hell decided wooden seats would be great for sitting through a concert?? The seating arrangements are laughable seating is sideways form the stage really? Waitress kept interrupting go back and worth not her fault because the tables are ridiculous long so the only way to serve the other table is to walk in front of you every couple of minutes really annoying when you are trying to watch what you paid for! Bathroom was disgusting!! Urinal was overflowing paper towel machine out of paper towels so the staff decided to instead of filling the machine just leave it on the wet sink for all to enjoy !! Staff was rude and unfriendly Bravo city winery you are the worst venue in the city of Chicago!

Eating at the restaurant is really a 'secondary' experience. Overall service is good but quality and selection of food is pretty average. We now go for the musical venue, order a bottle of wine with a cheese selection- overall this turns out to be an excellent occasion.

This is a nice intimate place to catch a show. Valet parking is available and the food, drink, and service are all very good.

We were watching WGN and one of the Comics from the show "Whose Life Anyway" was on. We decided to get tickets and go last night. The show was great but the dinner before was the bomb! We had the Dipping Flight for an appetizer. It was great. I don't know which I liked better of the three; Hummus, Eggplant or Beets. For dinner I had the Lamb Osso Buco, it was done perfectly and was great. My wife had the pork chop and it too was done perfectly. We will be back when we have another Whim!

I took my sister here to see Rachelle Ferrell. There's not a bad seat in the house. Acoustics are impressive. Service was excellent. We had dinner. It was okay, but the venue is comfortable and we had a good time. I would recommend it if there is an artist you enjoy. They sell out quickly. There is also street parking nearby if you get there early enough, buy valet parking is available.

We have been here for shows and dinner and a wine appreciation course so I guess it could be obvious that we enjoy coming here and partaking in their various offerings. Mostly let's talk food first. The menu in the large dining room ( Barrel Room ) is varied and has reasonable prices. It is rather complete, starting with small plate snacks and appetizers, tapas size and larger. These could be shared. So we shared a special pizza, and a burrata for starters. Each very good, especially creamy was the burrata. Split a Kale Caesar salad and each of us had larger plates really full size portions. The ruby trout is very nicely done. The interpretation of duck tacos was clever as you get a pot full of duck and build your own with all the trimmings. So while the menu has a tapas flair, the more expensive items are definitely major portions and serve as a dinner. Side dishes also available. We skipped dessert and went to music room across lobby. Terrific wine list and generous cocktails. Really a fine place to go and enjoy yourself, with any combination of drinking, dining or music either separately or a triple play all under one roof. I would like to offer a superlative review of the tribute band we saw perform the last time we were their this month. They were superb practitioners of the Talking Heads songbook. I believe the band calls itself Big Suit in this iteration. They are well versed and sound remarkably faithful to the originals. We have seen other worthy acts there. If you really have fav musician and they show up here you should truck on down. The music room has great acoustics and sight lines; it's not very big really, it's almost intimate. See for yourself. Street parking and valet parking available.

Nice atmosphere. Waiter started out really good. Recently moved back from TX. We were a large party, and I do know it takes time with large parties. Started with drinks. It should not take 30mins to bring a can of beer and a glass. It took over an hour to get our food and when we did, the fries were cold. One person ordered their shrimp skillet, how about 20mins later oh the two people that ordered the shrimp skillet, we don't have it. Those two had to get the menu again to order something else. Like I said I know large parties takes time. A good waiter with customer services skills would have come to the table, I do apologize for the delay today, can I get you all something to drink, or we would you all like an appetizer while we wait. But nothing. Waiter was slow, confused. Manager comes over later ask how was everything, he heard the brussel sprouts are burnt, oh we can get you more, Im sorry. No thank you, I will pass, at this point it had already taken over an hour to get that. Then he was told how the fries were cold, even the manager walked away after that. Terrible service and definitely not worth the price.

Large place with great wine selection. Went there for med school graduation. Staff very good. Food served cold, but large group. Staff rushed us through the meal. Just got app then started serving main course.

We saw Rufus Wainright; great venue. Food was a little hit and miss but highly recommend the Burrata. Ambience is top notch. Wine from City Winery was barely drinkable and not even worth $5 a glass much less $12 or $15. Suggestion? Go for the show you want to see snd pick some bottled wine that you know on the list.

This is a great place to take a break and enjoy a glass of wine. Get a counter stool if possible versus a table to really enjoy the parade on the sidewalk and water way. The wines are very good albeit a bit pricey. The food is good if you are looking for a light, simple nosh.

Great spot to see a show and get food . Went to see los lobos . Really great sound . Will hesitate to see another show here. Good food and service #porkmafia inda house

I think the wine and cheese/charcuterie were just average and slightly overpriced. Service was lacklustre too, probably because it was a rainy Sunday afternoon. Took a look at the food offerings and felt that they were quite overpriced too.

I have not been to a concert here since Chuck Prophet. The music was so loud we had to leave after two songs. I have been to 4 concerts here and the music is often so loud that even with earplugs in it’s painful. I cannot go back here because the music is just too loud. The room is small and there is no reason to have the music as loud as they do. People will have earplugs in and still have their hands over their ears. The food is decent and the wine is okay, but they jam you in like sardines. I wouldn’t feel too safe post covid going there unless they required masks and vaccine cards. I hope they have changed their policies post covid and spread things out a bit.

I don't normally write negative reviews, but I felt obligated to do this one. My husband and I were there at the end of April and chose this because we weren't very hungry and thought we could get a light dinner. One chicken panini and one lobster roll with 2 glasses of wine cost us over $100 dollars with tip. Now I know Chicago is expensive, but we felt this was VERY overpriced considering the food was barely average and the wines were not of the best quality. Now maybe they will improve as the summer continues but I cannot recommend this establishment. We were very disappointed.

As a French teacher, I am always looking for cultural opportunities and when a French group was set to come, I couldn't pass it up. Not only did we have some amazing entertainment, we also got a great meal, good wine, and great service as well. When you buy an entertainment ticket, you are also getting a seat at a table where wine, drinks, and food are served. They can be ordered at any time. I was concerned about parking, but for $13, you have great valet parking. Seating is on very narrow tables that you share with other people, but that is not an issue. We found out that the venue had a previous life, and in reconstruction, they used 75% of the materials, repurposing them. We arrived at 6:00 for the 8:00 PM show. We ordered a great French wine at first, a great Cabernet from the Loire Valley, something I don't find very often. It was wonderful. We then tried the wine they actually produce at the winery. It was excellent, and never even bottled, it came straight to the carafe. Our flatbread pizza was spectacular and even made using yeast taken from the wine production. We had a burger and that was equally good. The show was way beyond expectations, a French group that I have known about for years and whose music I have enjoyed greatly. Wow, what a great evening!

Stopped along the River Walk on a sunny afternoon to enjoy a glass of wine. We chose the Winery White and Rose and both were delightful. A great place to relax and enjoy Chicago.

We came for dinner as a group of about a dozen. We got a separate room for our group but only one server? I don't care how good that individual might be , a group this size warrants 2 servers to properly cater to its diners. We were often waiting to place drink orders and just got up and retrieved extra silverware from a nearby table. Food quality was pretty good even though some of the portions left a bit to be desired in terms of quantity ($10 for a hummus plate that looked like it should have been half that price). Overall ambiance and staff friendliness was very good.

Food was spectacular, service was stellar. The venue was just the right size to feel intimate, and really be able to feel the music and be a part of it.

Went for a concert. The seating is tight. You have people that turn their chair to the end of the table to have some extra room and this blocks everyone's view behind them. Not to mention making already tight walkway even tighter for wait staff and people getting up for whatever reason. Enjoyed the show though. Small venue made nice atmosphere. Just rude patrons. Nice staff members.

You’ve gotta go for a show of choice! It’s a fabulous spot to go with friends or on a date. The acoustics are on point. Dark lit setting, an intimate and beautiful venue. The house wines are awesome.

Had the most amazing time here for a girls brunch. Our server, David, was the best server we had during our time in Chicago. I cannot recommend this place enough! Amazing staff, great wine and great food.

My food and Server were both awesome. Seating is a tight fit if you are up near the stage so you need to take that into consideration when booking your seats. I have been there twice . The first time I booked further away from the stage as I was on crutches and had no problems. This time we were right next to the stage. I believe it was a sold out show so there wasn't a lot of wiggle room. Luckily the people sitting at the table next to us were very pleasant( we made our bathroom run prior to the show starting). There was one woman who was two tables away who was quite obnoxious about her food and everything and gave the wait staff such a hard time( prior and after but not during the concert). The staff was so gracious to her . I appreciate their class when dealing with her. I do love this venue for a concert. I will be back. We used Uber and Lyft to get to Venue but they do have valet parking for a fee.

What a great place to sit on the river!! Lots of people watching, boat watching, and great wines to drink while enjoying the views on the river!

We came for the Connor McLaren/Bob Schneider Show, which was amazing. The wine is tasty, and they have plenty of beers as well. Not a bad seat in the house. Ordering on your phone is a little awkward.

I have been a loyal fan of City Winery on Randolph Street for many years. If you enjoy live music in an intimate, energetic, fun-filled venue this is it for Chicago. Concert guests widely vary; Leon Russell, Makana, The Blind Boys of Alabama, Carolina and the Chocolate Drops, Semika Copeland to name a few. But ...the food is grand too! Eats here come in a wide selection to meet anyone's nutrition needs and preferences. The Italian Burrata will transport you to another side of the globe faster than you can whisper Mamma Mia! The liquids range from home brewed beer and wine to a nice global selection. Last night a trip to the blues world was outstanding with Tommy Castro & the Painkillers with special guest, Ronnie Baker Brooks (son of late, gifted Lonnie Brooks, who we sadly lost this spring). If the roof wasn't tightly secured it would have bounced off with the beautifully orchestrated 'get down' to the blues ...Chicago style. The staff are amazing, Jeff, Andrew, Vinny and the others are always professional. Food, drink, nice people and fantastic music makes perfection each and very time. Get yourself there soon!

Visited on a Sunday evening reservation required . Patio seating very lovely. City winery very deceiving as there are only 6 wines . No Chardonnay and no cab Sauvignon. Limited menus. Expensive but .. the Riverwalk adds to the ambience.

My husband and I saw Rachael Yamagata here, and we had the best time! I was hesitant buying tickets due to the reviews of the venue mentioning cramped seating, but I'm so glad I didn't let those reviews dissuade me. We opted to book a two-seat high top (table 406) in the mezzanine area. I would have been happy with any of the seating in Mezzanine or Mezzanine Premier. The Orchestra, Stage Premier, and Premier areas were more cramped, but as long as you know that's what you are getting, it would be fine too. Everyone down there was having a great time and there was a lot of interaction with the artist. We ordered food and drinks through our phone to limit conversations with waitstaff during the show, which was simple. There truly is not a bad seat for viewing the show. We were at the very back and it was perfect. The food was excellent as well.

We had the opportunity to see Susan Werner perform at the City Winery. The online ticket purchase process was great. We were able to pick our seats and when we got there we simply gave our names and were seated. The service was outstanding, and the room was perfect for the show. No bad seats from what I could see. We will definitely be returning. The line-up of shows is great, and shows are scheduled almost every night.

First time here for both dinner and show. The show was a hit with the group but the dinner left quite a bit to be desired. I'd recommend dinner at a nearby restaurant and then the show at City Winery.

The space is very nice and inviting. The ravioli did not taste homemade; the pork chop looked more like a deep fried pork tenderloin; the burger I ordered to be prepared medium was very well done! The salad would have been good except that it had been drenched in salad dressing! We were warned the food was not very good but I thought, how can you mess up a burger; well, they did. We went there to see Suzy Boggus and she did not disappoint. We were packed in like sardines but Suzy and her group made up for that although I do not look forward to returning to that venue; not comfortable.

We got a deal on a tour of City Winery through Travelzoo.com. The tour was just me and my wife, and our tour guide was Brittany (sp?). She was incredibly friendly and fun and gave us a very entertaining tour. Before starting the tour, she brought us both a glass of wine, which was only the beginning of the wine tasting. We drank our glasses all through the tour, which showed us the concert venue, the cellar, the dining room, and the ageing area. Then we were seated at a table and given 3 more glasses of wine. The glasses all had nearly full servings of wine, and all of them were delicious. Brittany even brought out more wine a little bit later, including an additional glass of cabernet to compare to the one she already provided us. Overall, we had a great experience, and wish that it had worked out in our schedule to have brunch here as well. Next time!

My husband and I had a great time. This was our 2nd year going, he did the Whiskey and I did the Wine. However, last year he bought 2 Whiskey passes by mistake and he had to repurchase me a wine one and he drank all the whiskey from my passes as well as his. The freebies were a pleasant surprise too, from noodles, to coffee, to packages of napkins, tums, etc. Love my free state farm bag and other freebies we received. We may not return next year simply because I would like to try to Taste of Chicago. Thank You. Phoebe Anthony St Louis, MO

I thought this place was decent until I was sitting outside and noticed a strange movement behind the plants along the edge of the patio. I soon realized there were multiple rats running through there.

It's all about the wine! We haven't eaten much there, but the wine selection changes frequently so there's always something new to taste. Their palate and ours must be similar, and it's brilliant to have so many dry wines on offer. It's a good idea to check and be sure there isn't a private event before going; we tried to go twice in Nov/Dec and found it closed. If you sit at the bar, talk to the bartender - they know a lot about the wines!

Right in the river. Sipping some wine. Watching Chicago go by. Couldn't beat it if you tried. Well...if you improved the wine list. That would beat it. Good service though and nice little cheese plate. Hard to screw up charcuterie and they didn't. Just really would have liked some bigger choice of wines. I do get space is limited here so that's why the lean into 4 stars instead of back to 3. I mean the wine cellar would be on lower lower Wacker so...worth a night of your stay or even just a late afternoon

This place is the best venue to see a concert in an intimate setting. Love everyone who works here, they treat you like family.

Beautiful decor, nibbles were great, staff also! But it was all about the music and the musicians! Can't wait to come and see some other acts!

Attended the Lee Ann Womack concert and had a great time at this very nice venue. It is a smaller sized room for a liver performance with no bad seats. The tables are small so some creative plate placement is in order. Very friendly staff. We attended a Sunday night concert so parking was free and easy on Randolph. The room had had a great sound and your up close to the stage. The food is good and not over priced considering your downtown. You can order and eat before and during the show.

Second time at City Winery and both times the venue was perfect. This time we had seats in the back and I was concerned it would be a problem. But it is elevated and the sound and view were excellent. We arrived at 6:00 and thought it would be a long wait for the show (Kurt Elling who was fabulous). But our table for 8 quickly filled up with very interesting people and we ordered food....the burger which was excellent. The time passed quickly and was enhanced by our great server, Ray. Super personality! Needless to say the wine was excellent! Cannot wait to return for another perfect evening!

The convenient location is really great for sightseeing. I like the river views (east, west, north, and south). I enjoy relaxing whenever possible.

tricky to get here and even trickier to get back to downtown Chicago...not many cabs around after the show. We have been here twice and both times we loved the place. Great food, great drinks, reasonable prices and wonderful guest performers. Last night we saw Basia and they were terrific! Our waitress Michele did a wonderful job of bringing drinks and food to dark, tight spots and we never missed a beat of the show. Highly recommend this place. Hoping to go back in November for another favorite, Pokey LaFarge!

Really great space for business dinners, weddings, holiday parties, wine education, music, food, beverages. It’s all amazing and fun

Went there to see the band The Church on July 3. The place is great to see a show and the staff was friendly and knew their wines.

So, if there is a band you like playin by all means go. The venue is fairly small so you will be able to enjoy the music and see the band clearly. There are tables and chairs radiating out from the stage which allows you to in theory enjoy dining and music simultaneously. Staff were pleasant. Food was very mediocre - and seriously overpriced. Wine list was ambitious and I thought poor value. Would I go back? Absolutely if there was a band I was interested in but I would eat elsewhere before the show and enjoy the show with a draft beer from one of the local microbreweries.

I've been here for music performance and for a wedding. The wedding worked out well in the space. It was in the summer so it started outdoors and moved indoors. A job well done. The music experience was good because of the size of the room. The food is average and the wine is well wine. I never yearn to go here, but can't say that I have been unhappy. It just lacks that "secret sauce" that some places have.

City Winery does it all, good food ( some of the BEST burratta in the city!) wonderful entertainment all in an intimate venue. I have been there 6 times and have sat in different seats each time, there is not a bad seat in the house. The acoustic are wonderful and it is a really a treat to see and hear music so close. The wait staff is wonderful too. Check out their schedule there is something everyday.

On the river walk, sitting outside enjoying the boats going by. The wine & appetizers are really nice.

We bought tickets to see a comedian here in mid-February. Thankfully, we bought them early enough that we were able to choose a two-person hightop table rather than a cramped table sitting across from or shoulder to shoulder with strangers. Some people even stopped by to say they were jealous of our seats. Although we were glad to be as isolated as possible (although our table was still so close to the others that people kept bumping into my crossed leg) we were quite unhappy with the discomfort of the hard seats we sat on for two hours. We had already eaten dinner at a nearby restaurant, so we did not purchase any food. My husband ordered two drinks but the drink service was slow. Valet parking was $16. Overall, we would not return here unless there was another act that we just had to see.

Awesome, intimate venue to see some fantastic artists. I was very concerned about getting the right real estate when I purchased my tickets, but there really wouldn’t be a bad seat. Warm and cozy. Can’t wait to go again!

Staff is very rude like if they doing you a favor for seating you Even the manager got a cocky actitud.

My wife and I went to see Lizz Wright, and truly enjoyed our visit!! Buck, our waiter, was extremely helpful, made a Birthday Surprise possible, and made our visit so comfortable! The wine was wonderful, and the atmosphere was so quaint, yet fun!! We would LOVE to come back and see another show!!

We were excited to listen to Jennifer Hartswick, who we’d never heard before, and has a wonderful voice. Our seats were ideal to view the stage, hear the music, and see over the main crowd. However, the couple next to us loudly talked and drunkenly laughed through each song. I informed them we wanted to listen to the music and asked them to do the same. They kept talking and laughing. We asked the server if she could “shut them up” and she brought the manager out. The manager informed us that we had to move and that people can disrupt the performances if they so choose. I was stunned, because the opening announcement asked the audience to refrain from talking during the performance. We won’t ever attend another performance at City Winery. The food was good, but the wine was not good.

This is a great venue but has a very limited food selection. It is a great location for couples and friends.

We visited City Winery on our last night in Chicago. I wish we had found it sooner! It quickly became one of my favorite places we visited. They have a limited wine and beer menu, but it has a little bit of everything. We did not eat here, but heard the food was good. You can go to the walk-up bar, order your drinks, and then take them to the steps in front of the winery and sit to watch the River. Peaceful and gorgeous.

Two questions, what is the actual BRAND of City Winery? Also, does City Winery and its staff REALLY care about the customer experience? I walked away from this evening's Marquis Hill's performance with an EMPHATIC no. I voiced my displeasure of the evening with Tyler Gordon, the Service Manager, who gave the excuse of people called off and suggested that it was in some way our (my date and I) fault because we did not come 2 hours before the show.   When asked how could he make things right, I explained I have identified that the service we received was subpar, and he should figure out how to deliver on their promise or brand...note I never saw him again, although he knew my name and table number 412---no follow-up, no comps, could care less -so the statement for the evening this is how we treat you, deal with it...NOT.   Michael and Nathan you and I need to have a conversation. The staff reflects leadership and no one cares. Zero integrity whatsoever.

We’ve been here three times this year for music, and loved the concerts. Nice site lines, intimate setting and friendly staff. Valet parking is $16. Drinks are a bit overpriced. We decided to eat here the other night, pricey, and not great. The food was salty and dry… really was not impressed. Tommy our server was good.

I'm not a Wine Drinker but there is tons of wine everywhere every table seem to have wine looks good. The service was not that great then and get refills on our drinks had to wait around for the waitress. The food portions are not large so just wanted to let you know that in advance. The chairs look more like retro which is really pretty. Enjoy