Madeline & Keenan

Madeline & Keenan

Saturday, September 27, 2025 • Chicago, IL
144 Days To Go!
Madeline & Keenan

Madeline & Keenan

Saturday, September 27, 2025 • Chicago, IL
144 Days To Go!

Things to Do

Where do we even start!? Chicago has endless amazing restaurants, shows, sporting events, museums, activities, and neighborhoods to explore. While our list could go on forever, we’ve provided some of our favorite local spots below.


In the Neighborhood - Activities

Lakefront Trail

Picture of Lakefront Trail

The lakefront is only 3 blocks east of the hotel and is great for a bike ride, walk, or to lounge on the beach (concrete or sand).

Green City Market Lincoln Park

Picture of Green City Market Lincoln Park
1817 N Clark St, Chicago, IL 60614, USA

This farmers market in Lincoln Park is the perfect spot to grab a coffee or pastry on Saturday & Sunday mornings.

Website

Lincoln Park Zoo

Picture of Lincoln Park Zoo
Chicago, IL 60614, USA

Walk through Lincoln Park and check out the zoo which is free to enter and explore.

The Second City Comedy Club

Picture of The Second City Comedy Club
230 W North Ave, Chicago, IL 60614, USA

Attend a comedy & improv show at the famous Second City comedy club to see where many SNL stars got their start in comedy.

In the Neighborhood - Places to Eat

Breakfast, Brunch & Coffee

- 3rd Coast Café - perfect for a a classic diner breakfast

- The 3 Arts Club Café at RH Chicago - great for a fancy brunch in a beautiful atmosphere

- Blue Door Kitchen & Garden - sunny patio with a delicious brunch & lunch menu

- Gotham Bagels - make sure to order ahead online. Pro tip - ask for their homemade hot sauce!

- La Colombe Coffee - there might be a line but it's worth it for their draft latte

- Philz Coffee - delicious pour over coffee

Dinner & Drinks

Check out the bars and restaurants along Wells Street or Rush Street. Our favorites include:


- Sparrow - cozy speakeasy bar with great cocktails

- LuxBar - lively bar and restaurant perfect for any time of day

- Small Cheval - grab a burger and fries and hang at their casual outdoor patio

- Zebra Lounge - intimate piano bar with great live music. Just don't forget cash!

Other Chicago Classics

Chicago River Boat Architecture Tours

Picture of Chicago River Boat Architecture Tours
112 E. Wacker Drive

One of the best ways to explore the city and learn about all of the stories behind Chicago's buildings and architecture.

Cubs Game at Wrigley Field

Picture of Cubs Game at Wrigley Field
1060 W Addison St, Chicago, IL 60613, USA

Riverwalk

Picture of Riverwalk
Chicago, IL 60601, USA

Explore the Riverwalk downtown by grabbing a drink or taking a stroll along the river.

The Green Mill

Picture of The Green Mill
4802 N Broadway, Chicago, IL 60640, USA

Experience live music at a classic Chicago Jazz club. Our favorite is The Green Mill!

Cloud Gate

Picture of Cloud Gate
201 E Randolph St, Chicago, IL 60602, USA

The Art Institute of Chicago

Picture of The Art Institute of Chicago
111 S Michigan Ave, Chicago, IL 60603, USA

For the Foodies

- Try an Italian Beef from Al's Beef (or Mr. Beef for fans of The Bear)

- Grab a Chicago hot dog from Portillos, Devil Dogs, or a Cubs game (our favorite)

- Au Cheval burger - it's worth the wait, trust us!

- Tapas at Café Ba-Ba-Reeba/Lil-Ba-Ba-Reeba - always a go to for shareable plates