Fantastic 2nd visit to Chicago

Question

Just back from a brilliant 8 days in Chicago. So much great advice on here that really helped us. I thought I’d share a few highlights in case it’s useful for anyone.

Travel - we came into O’Hare at lunchtime, so downloaded the Ventra app and added a 7-day pass, which is great value at $20. Headed to downtown Chicago on the CTA blue line, included in the pass and a simple journey even with luggage.

I have to say that the whole transport system in Chicago is so easy to navigate, inexpensive and we never waited long for any bus/train. We used buses the most as it gave us lots to look at as we travelled. We used the Metra train to Winnetka to see the Home Alone house - good value on a weekend at $7 each for unlimited rides for one day.

Food - as with any major city the choice is endless and given we had kids in tow, we had lots of options on the list. The absolute highlight though was Pequod’s Pizza in Lincoln Park, best deep-dish we had by a mile - and we did try a few. Our favourite breakfast spot was Pittsfield Cafe, big portions too. For lighter bites Paris Baguette on the corner of 11th and Michigan was superb, with lots of incredible pastries. We tried Al’s Italian beef sandwich and it was good but not sure it lived up to the hype. Levain Bakery and Crumbl were both favourites, if you want a sugar rush :)

Sport - we did two NBA games, one ice hockey and one baseball. For the Bulls and Blackhawks games we used the buses from Michigan Avenue, #20 on the way and #19 to return. The whole set-up is just brilliant, the buses start 90mins before the game and on the way home they are all nicely lined up outside United Center. I’ve not seen anything quite so organised in the UK, this was very easy. We stayed near Grant Park so had around a mile walk from the bus drop off, even at 11pm this felt very safe in our experience. For the baseball we jumped on the CTA red line, got off at Addison right outside Wrigley Field. A incredible place steeped in history and a great atmosphere. We sat in the 400s, which was very high up but with a perfect view. Could barely feel my legs as it was so cold, but to be expected and we really enjoyed it. Bonus was I got chatting to one of the local fans in the seat next to me, so I’m a little more aware of the rules now :)

We also visited the wonderful Lincoln Park Zoo, which is fantastic and completely free. We were lucky enough to meet a retired volunteer who knew so much about the animals and the history of the zoo.

We braved the cold and hired bikes from Bobby’s Bike Hire. Joe was super helpful with tips on where to go, so we ventured down to Shedd Aquarium on the Lakefront Trail then back up North Avenue beach - great fun and some amazing pictures.

Only one day of torrential rain, so we headed to Rosemont on the CTA blue line, then the free bus to Fashion Outlets of Chicago to grab a few bargains in the sneaker shops - particularly Nike and Under Armour not to be missed.

On the last day we visited the Chicago Sports Museum. This was good but you don’t need long there, so you have to weigh up if you feel it’s worth it. We also jumped on the Chicago Water Taxi from Chinatown to Michigan Avenue. At $10 each is was good value and the sun was shining so we got some great photos.

Overall, a wonderful trip and we will definitely return again.

Answer

It sounds like you had an incredible time in Chicago, and it’s great that you’re sharing your experience! Here’s a breakdown of your highlights for anyone visiting the city in the future:

Travel: You made great use of the Ventra app for transport. The $20 7-day pass is indeed an excellent value for getting around the city, especially on the CTA. The Blue Line to downtown from O'Hare is straightforward, and the CTA system in general is known for being easy to navigate. I also love that you got to experience the Metra train to Winnetka for the "Home Alone" house — that sounds like a fun detour!

Food: You certainly explored a lot of Chicago’s food scene! It’s great to hear that Pequod’s Pizza in Lincoln Park was your top pick for deep dish — it’s a local favorite for sure. The Pittsfield Cafe for breakfast is also a great choice, with its huge portions. Paris Baguette is a gem for pastries, and Levain Bakery and Crumbl are perfect for anyone with a sweet tooth. It’s understandable that Al’s Italian beef didn’t blow you away, as it can be an acquired taste, but it’s still worth trying while in Chicago.

Sports: You really immersed yourself in Chicago’s sports culture with NBA, hockey, and baseball games! It’s fantastic that you found the transit system to be so efficient. The #20 and #19 buses for the United Center are great, and the CTA Red Line to Wrigley Field is the easiest way to get to a Cubs game. Wrigley Field is definitely iconic and has such a great atmosphere, even on a cold day. The Chicago sports culture is part of the city’s charm, and it sounds like you had a great time, especially getting tips from a local fan!

Zoo and Bike Hire: The Lincoln Park Zoo is a hidden gem — free to enter and full of great exhibits. It’s fantastic that you had the chance to meet a knowledgeable volunteer, as that often adds so much to the experience. Also, biking around Chicago is a great way to see the city, and hiring bikes from Bobby’s Bike Hire and cycling along the Lakefront Trail sounds like a perfect way to enjoy the sunny weather. North Avenue Beach and the Shedd Aquarium are both great stops for scenic views and photos!

Shopping: Fashion Outlets of Chicago in Rosemont sounds like a solid rainy-day option. With Nike and Under Armour stores, it’s a great place for any sportswear shopping. The free bus from the CTA Blue Line to the outlets makes it easy to get to, and it's nice that you were able to grab some bargains during your trip!

Other Attractions: The Chicago Sports Museum is a fun stop for sports enthusiasts, though it sounds like it’s one of those places you can enjoy in a short visit. The Chicago Water Taxi is a great way to see the city from a different angle and to catch some beautiful photos, especially if the weather is nice. It’s a unique way to experience Chicago's waterfront and the city skyline!

Conclusion: Sounds like your trip was packed with adventure and a great mix of sightseeing, sports, food, and relaxation. Chicago is such a diverse city with something for everyone, and it’s clear you took full advantage of that. Thanks for sharing your recommendations, and I’m sure future visitors will find your tips helpful. Looking forward to hearing about your next trip to Chicago!