Itinerary feedback

Question

Hello! Headed to Chicago on Thursday and looking for some feedback/advice on my itinerary. Especially struggling with my Sunday and early Tuesday before our flight out. I’ve been to the surgical and art museum already, no interest in navy pier. I’m trying to squeeze in a trip to ricobenes somewhere.trying not to be super touristy, but I think I’m failing. I know opinions are strong, but Pequods and Mr Beef are non negotiables 😆 Would love some input on things that aren’t eating or drinking in Lincoln park/Chinatown areas. I’m just copying and pasting, so please disregard my notes

Chicago

Thursday, May 22

Arrive O’Hare 10:30

Train to LondonHouse, drop luggage

Brunch at Good Eating (down the riverwalk from LH)

Bridge House Tour (if time)

Architecture Center Boat Cruise 2:00-3:30 (112 E. Wacker @ 1:30)

LondonHouse to refresh

4:30 walk up for bar seating at Bavette’s 🤞🏼

Drinks Gilt Bar Library

8:00 Swing orchestra at Green Mill (Uber) *CASH ONLY

Uptown deli sandwiches (late night munchies - open til midnight) 5 min walk

Uber to LH

LH rooftop nightcap (before midnight)

Friday, May 23

Rent bikes, lakeshore trail:

Oak Street Beach

Original Pancake House

North Avenue Beach (walk or bike)

Lincoln Park Conservatory

Portillos lunch

LH refresh

River North Speakeasy “tour”:

Spin, LuLus, Storyville…

Pequods late night (uber)

Saturday, May 24

Walk to Chicago Athletic Association (late) breakfast at Cherry Circle Room, cocktails at Cindy’s

Cultural Center

Milennium Park

CAA game room/drawing room

Grant Park/fountain

????

7:00 AC/DC concert @ Soldier field

Sunday, May 25

Water taxi to Ping Tom Park

Chinatown

?????

Monday, May 26

Mr. Beef 10:00am

Wrigleyville:

Murphy’s

Sluggers

Cubs game 1:00

Graceland Cemetery

Small Cheval (walk)

Magic Lounge (uber)

Tuesday, May 27

?????

O’Hare by 1:30

4:00 flight

Any help is much appreciated!

Answer

Your itinerary is already packed with great activities, but I understand you're looking to make some tweaks, especially around your Sunday and early Tuesday. Let's go through each day and see if we can fine-tune the schedule and add some non-touristy experiences in Lincoln Park and Chinatown!

Thursday, May 22

This day looks solid! You've got a great mix of activities, with a nice balance of sightseeing and dining. Here are a few thoughts:

The Architecture Center Boat Cruise is a must-do if you haven't already done one. It's a great way to see the city from the river and learn about Chicago’s iconic architecture. If time allows, try to add a stop at the Chicago Riverwalk afterward to explore a bit more by foot.
The Green Mill is a fantastic choice for jazz. It's iconic! Just be sure to get there early, especially if you're hoping for good seating. It's cash-only, but definitely worth the visit.

Friday, May 23

You’ve got some fantastic stops here too, but a couple of things to consider:

For bikes, the Lakeshore Trail is a great idea! Make sure to stop at North Avenue Beach and grab some coffee at the Little Goat Diner nearby if you’re in the mood for a small break.
Portillo's is a Chicago classic! If you’ve never tried their chocolate cake, don’t miss it!
Your speakeasy tour sounds like a lot of fun—Spin and Lulu's are great choices. Another speakeasy to consider for your list is The Violet Hour in Wicker Park. It's a bit more tucked away, but very cool.

Saturday, May 24

This day has a lot of great options already, but you might want to consider adding something like:

After the Cultural Center, take a quick walk over to Millennium Park for the Cloud Gate (The Bean), then head to Grant Park for the Buckingham Fountain.
For lunch, you could check out The Art Institute’s café (if you’re into museums), or grab a quick bite at Revival Food Hall, which has a range of great local food vendors.
After your AC/DC concert, if you're up for more, check out the Chicago Athletic Association game room. It’s a cool spot for some post-concert fun, or you could visit The Violet Hour for a late-night drink!

Sunday, May 25

For your Chinatown day, it looks like you’ve already got the Water Taxi to Ping Tom Park and some Chinatown exploring covered, but here are a few ideas:

In addition to exploring Chinatown, stop by Chinatown Square and try Joy Yee's for a casual bite or Triple Crown for some classic dim sum.
Head over to Old St. Mary’s Church, one of the oldest churches in Chicago, for a little history and architecture.
If you’re into gardens, you could visit the Chicago Botanic Garden or the Lincoln Park Conservatory after Chinatown.

Monday, May 26

This day is also packed, but here's a suggestion to mix things up:

Before heading to Wrigleyville, you could take a quick detour to Graceland Cemetery (which is fascinating) or explore Lincoln Park, which has a great zoo (free to visit) and is perfect for a stroll.
If you’re into quirky stops, consider checking out The International Museum of Surgical Science before you head to Wrigleyville.
For a late-night stop, check out Magic Lounge, which you’ve already planned. It’s a great spot for a little magic and cocktails.

Tuesday, May 27

Before your flight, here are a few things to consider to fill the day:

If you're not in a rush, stop by Lincoln Park Zoo or explore the Chicago History Museum for a bit more Chicago history.
Another fun idea could be to grab breakfast or brunch at Beatrix in River North or Wildberry Pancakes near Millennium Park before heading to the airport.

In general, your itinerary looks fantastic. You're covering a lot of great neighborhoods, from Uptown to Lincoln Park to Chinatown, and balancing iconic attractions with local spots. You're already doing a great job of avoiding too much of the “touristy” stuff!

Hope this helps with your planning and that you have a fantastic time in Chicago!