Chicago is a vibrant city that I have had the privilege of exploring over the last three years. I’ve had the opportunity to experience the best that the city has to offer from amazing food, incredible sports, and the hottest entertainment. Whenever a friend or acquaintance comes to town for 2-3 days and asks me “What would you recommend we go do?” I send them the following list. You won’t have time to do it all, so pick a few activities and a few restaurants/coffee shops to round out your long weekend itinerary.
Professional Sports
Chicago has an amazing professional sports scene: no matter what time of year you are visiting, you can check out top notch teams:
| SPORT | TEAM NAME | MONTHS YOU CAN CATCH A GAME |
|---|---|---|
| Men’s Hockey (NHL) | Chicago Blackhawks | October – April |
| Men’s Basketball (NBA) | The Bulls | October – April |
| Women’s Soccer (NWSL) | Chicago Red Stars | April – September |
| Baseball (MLB) | White Sox AND Cubs | April – September |
| Women’s Basketball (WNBA) | Chicago Sky | May – September |
| Football (NFL) | The Bears | August – December |
| Men’s Soccer (MLS) | Chicago Fire | March – October |
Live Entertainment/Venues
- Architecture Boat Tours: I love architecture boat tours. I’ve been on multiple due to the number of visitors that have come to see me in Chicago. You will wind around the city via the Chicago River while learning more about the history of Chicago and the buildings. There are a lot of great tour operators, my personal favorite is run by the Chicago Architecture Center.
- Comedy: Some notable comedians have come through Second City enterprise including Stephen Colbert, Tina Fey, Steve Carell, Conan, Mike Meyers. There are multiple stages, but my favorite is the main stage. As another option, I also really enjoyed the Improvised Shakespeare Company with my friends-they improvise everything while in Shakesperean costumes and speak.
- Music: Some of my favorite experiences so were seeing Buddy Guy play in his venue Legends (January only!) and the Salt Shed. Check out this article from Choose Chicago for an additional 30 music venues from large to intimate.
- Festivals: locals know that Summer is when the city of Chicago COMES ALIVE: we suffer through the winters for the privilege of hitting up all our favorite festivals on weekends throughout the summer months. With that being said, we have festivals all year round! Case in point, in December I love visiting the Chriskindlmarket Christmas market in Wrigleyville; make s’mores, drink spiked hot chocolate or Glühwein, go ice skating in the middle of Wrigley Field-so cute, so demure. So, bundle up and get outside, even if it’s cold. Choose Chicago has a great guide that highlights festivals by month.
- Museums: There’s a museum for every vibe!Art Institute, Museum of Science and Industry, Field Museum, Medieval Torture Museum, Chicago History Museum, Adler Planetarium, and so much more!
- Navy Pier: This is on the more touristy side of things. Ride the Ferris wheel and other games, ride around the lake on a boat tour (different from architecture tour).
- The Bean: located in Millennium Park, no trip to Chicago is complete until you’ve taken a selfie with the Cloud Gate sculpture!
Other Activities
- Walk the path by the Chicago Riverwalk and enjoy a beverage by the water
- Grab a drink at CloudBar 360 which sits at the top of the John Hancock building
- Go to the top of the Willis Tower (previously known as the Sears Tower)
- Rent a bike or walk along the 18 miles of lakefront trail
- Play volleyball on North Avenue Beach or try SUP (summer months only)
- Visit Eataly to visit one of several restaurants upstairs or browse the Italian market on both floors
- Explore the Starbucks Reserve Roastery bar on the top floor to enjoy a delicious espresso martini
- Rent a speedboat and go cruising along the Chicago River or Lake Michigan
- Sunset Dinner Cruise
- Rent a kayak and paddle through downtown Chicago
- You can do this on a tour or rent some kayaks by the hour and do your own thing. I used Kayak Chicago and they did a great job, but other tours have great reviews as well
- Walk around Lincoln Park; visit the Lincoln Park Zoo (it’s free!), Lincoln Park Conservatory, or have a picnic in the sprawling green areas near the lake
- Magnificent Mile for shopping; you can find both luxury and affordable brands
- Lincoln Park or Logan Square Farmer’s Market (Sundays April-October)
Off the Beaten Path
Most tourists don’t leave the downtown, but if you want a different vibe for dinner one night, here are several neighborhoods to check out:
- Lincoln Park
- Old Town
- Wicker Park
- Logan Square
- Andersonville
- Lincoln Square
- West Loop
- South Loop
- Lakeview
- Wrigleyville
- Ukrainian Village
- Chinatown
Chicago is an amazing city and I hope you fall in love with it the way I did. Did I miss anything on my list? Comment below!
