There is so much to do and see while you are in Chicago. Here's some of our favorite bars, restaurants and activities!
Chicago Riverwalk
Chicago Riverwalk, Chicago, IL 60601, (877) 300-6746
Grab a drink at City Winery on the Riverwalk or check out the Chicago Brewhouse.
Chicago Boat Architecture Tour
401 North Michigan Avenue, Chicago, IL 60611
Weather permitted this is absolutely worth it. Enjoy a 60-75 minute tour on the river and learn about Chicago's history. Don't worry, you can buy drinks on the boat.
Zanies Comedy Night Club
1548 North Wells Street, Chicago, IL 60610, (312) 337-4027
Best stand-up night club in the city! Buy tickets in advance if you are interested. If you prefer stand-up over improv this is the place to go. Bryan and I prefer Zanies to The Second City.
The Second City
1616 North Wells Street, Chicago, IL 60614, (312) 337-3992
All the best performed here - Tina Fey, Chris Farley and others! The improv/skits here are unforgettable. The main stage has the best shows and you need to buy tickets in advance.
Eataly Chicago
43 East Ohio Street, Chicago, IL 60611, (312) 521-8700
This is a fun way to drink wine and taste different Italian food! Casual dining, shopping, and drinking.
Happy Camper Pizzeria
1209 North Wells Street, Chicago, IL 60610, (312) 344-1634
This is our favorite pizza in Chicago! Beware it's not traditional Chicago deep dish style. It's in a great location with a lot of other restaurants and bars nearby. The Tony and The Curt are our favorites.
Jeni's Splendid Ice Creams
1419 North Wells Street, Chicago, IL 60610, (312) 877-5880
Best homemade ice cream in the city. Brambleberry is a must have!
Three Dots and a Dash
435 North Clark Street, Chicago, IL 60654, (312) 610-4220
Bryan's favorite! Unique tropical tiki bar hidden in an alley. The drinks can be expensive but you'll never see anything like it.
Flight Club Chicago
111 West Wacker Drive, Chicago, IL 60601, (312) 284-2474
Great place for all ages and if you have a large group. Play darts, enjoy drinks and small bites. Call in advance to rent out a dart lane.
Cindy's Rooftop
12 South Michigan Avenue, Chicago, IL 60603, (312) 792-3502
Overlooks Michigan ave and Millennium Park. Great view of the city. It's a popular place on the weekends so there can be a line to get upstairs.
Cloud Gate (Chicago Bean)
201 East Randolph Street, Chicago, IL 60602
Popular tourist attraction. In the middle of Millennium Park offering great views of the city. If you've never been to Chicago it's something to see at least once.