Trip itinerery - 3 days in Chicago - Feedback welcome

Question

My husband ad I are planning a trip to Chicago for this September. We're a pair of middle aged nerds. This trip is solely for fun and sightseeing. I've only ever been to Chicago for work related conferences. We're planning a 5 day trip, 3 days in the city and a travel day on either end.

So far I've only booked the flights and hotel. We'll fly out on September 21 (Sunday), have 3 full days to explore the city, and then fly home on Sept 25. We’ll be staying at Virgin Hotels Chicago in the northeast corner of the Loop, near the river. We’re planning on using mostly transit to get around while we’re there. A 7-day unlimited ride pass from CTA is only $20 per person, and we can take the blue line from the airport to our hotel.

I have quite the list of things to do, and have been paring that down to a workable itinerary. Feedback is welcome, as are restaurant recommendations.

Day 1 – Arrival

8am - Arrive at O’Hare. Blue line to downtown and drop our bags at the hotel.

10am - Breakfast/brunch at Miss Ricky’s (hotel restaurant). Wander through Millenium Park

2pm - McCormick Bridgehouse guided tour

3pm – Check into the hotel and take a much needed rest

6pm – Check out Navy Pier. Dinner somewhere in the area. Maybe walk around the pier (photo op with the Bob Newhart statue). Ride the Centennial Wheel. Maybe get dessert at Rainbow Cone.

Day 2 – Chicago Highlights

7:30am – Breakfast at Wildberry Pancakes

9am – Willis Tower/Skydeck

10:30am – 12:30pm - CAC River Cruise (tour is at 11, need to arrive by 10:30)

Lunch at Lou Malnati’s for deep dish pizza

Stroll up Michigan Ave/Miracle Mile

2:30 – Hancock Tower/360 Chicago. Maybe have a drink at the Cloud Bar

Return to hotel to rest and change

6pm – Andy’s Jazz Club – Dinner and early show (a jazz/blues show in Chicago is on my must do list)

Day 3 – Griffin Museum of Science and Industry

Breakfast (Suggestions welcome)

9:30am – 4pm – Griffin Museum of Science and Industry (This is my husband’s must do activity). We can easily fill a whole day here. We will be doing both the submarine and the coal mine exhibits.

Garden of the Phoenix/Jackson Park

Dinner – MCCB was recommended. I think it would be neat to see China Town. Not sure about the logistics of getting there from Griffin MSI.

Day 4

8am – Breakfast at Lou Mitchell’s

9am – International Museum of Surgical Sciences

Stroll through the southern portion of Lincoln Park. Possible landmarks include Lincoln the Man statue, Chicago fire relic

Lunch at Orso’s

Shopping at Judy Maxwell Home (Tchotchke shop owned by Joan Cusack. This is another request from my husband).

Return to hotel to rest

6pm – 7:30m – Lake Michigan Sunset Cruise (Wendella Tours)

Dinner – Recommendations welcome for our final dinner in the city. The Purple Pig is a possibility.

Day 5 – Homeward bond

7am - Breakfast (Miss Ricky’s or room service)

8am – Blue line to O’Hare. Flight leaves at 11am

Answer

Your itinerary for Chicago looks fantastic! You’ve got a great mix of sightseeing, culture, food, and relaxation. I’ve provided some suggestions and minor tweaks to help make your trip even more enjoyable. I’ve also added some restaurant recommendations for each day based on your interests.

Day 1 – Arrival

Your first day looks pretty relaxed, which is perfect for settling in after a flight. Starting with brunch at Miss Ricky’s is a good choice. Here are a few thoughts:

McCormick Bridgehouse guided tour: This is a fun, unique experience that offers great views of the river and some history about the city’s bridges. Consider it an underrated gem!
Navy Pier: For dinner near Navy Pier, Shore Club is a great option if you like seafood with a view. If you’re in the mood for something casual and fun, try Giordano's nearby for deep dish pizza after a Centennial Wheel ride.
Rainbow Cone: This is a Chicago classic for dessert! Definitely a must-try if you love ice cream. If you’re looking for something a little different, try Bobtail Ice Cream for homemade, artisanal flavors.

Day 2 – Chicago Highlights

Your second day is packed with the best of Chicago’s iconic attractions. Here are a few suggestions:

Willis Tower/Skydeck: The Skydeck is amazing for views, but if you want to avoid crowds, try to go early in the day. It’s much quieter before the tour buses arrive.
Chicago Architecture Foundation River Cruise: Highly recommended for architecture lovers! It’s a perfect way to see the city's iconic buildings along the river. Consider bringing a hat or sunscreen as it can get sunny on the open-air boat.
Lou Malnati's: Excellent choice for deep dish pizza! If you want to try another Chicago classic, consider Art of Pizza or Pequod's Pizza for a different spin on deep dish.
360 Chicago (Hancock Tower): If you go during sunset, you’ll get stunning views. If you’re up for it, try the Tilt experience for a thrilling vertical view of the city!
Andy's Jazz Club: This is a great spot for an authentic Chicago jazz experience. It’s very cozy and offers great live performances. If you're into jazz, definitely a solid choice.

Day 3 – Griffin Museum of Science and Industry

Spending a whole day at the Museum of Science and Industry is a great idea for nerds! It’s massive, so you’ll definitely need plenty of time. A few tips for this day:

Breakfast: Consider Yolk in the South Loop for a hearty, tasty breakfast. They have a wide variety of omelets and other options.
Griffin Museum of Science and Industry: Since you’re planning on seeing both the submarine and coal mine exhibits, be prepared to spend at least 4 hours here. The coal mine is a must-see!
Garden of the Phoenix/Jackson Park: After the museum, stroll through the beautiful Jackson Park and check out the Japanese garden in the Phoenix area. It’s peaceful and perfect for a post-museum break.
Dinner in Chinatown: MingHin Cuisine is an excellent choice for Chinese food. It’s quite popular, so be prepared for a wait, but it’s worth it. To get there from MSI, consider taking the bus or a quick Uber ride (about 10-15 minutes).

Day 4 – Museums, Lincoln Park & Shopping

This day looks great for exploring the city’s cultural side. Here are some suggestions for the day:

International Museum of Surgical Sciences: This museum is quirky but fascinating, and it’s much less crowded than Chicago’s more popular spots. If you’re into medical history, you’ll enjoy it.
Strolling Lincoln Park: Don’t miss the Lincoln Park Conservatory, which is a hidden gem in the area. If you enjoy gardens and nature, it’s worth the stop!
Lunch at Orso's: Great pick! Another excellent spot nearby is Piccolo Sogno for amazing Italian food if you’re craving pasta.
Judy Maxwell Home: Perfect for tchotchke lovers! You’ll find unique, quirky items here, and it’s a great way to get a feel for the Chicago shopping scene.
Lake Michigan Sunset Cruise: This is an incredible way to experience the city skyline. Consider booking a cruise with Wendella Tours for a relaxing evening on the water.
Dinner: The Purple Pig is a solid option for your final dinner, but if you want something a bit more upscale, consider Alinea (if you’re into fine dining) or Girl & The Goat for delicious shareable plates.

Day 5 – Departure

Your departure day is pretty easygoing, which is nice after your busy trip. A quick breakfast at Miss Ricky’s or room service is perfect before heading to the airport.

Overall, your itinerary looks well-rounded with a perfect mix of sightseeing, food, and culture. I think you’ve picked some great spots to explore, and you’ll definitely have a fun and memorable trip!

Trip itinerery - 3 days in Chicago - Feedback welcome

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