31 Things to Do in Chicago This Winter

Chicago certainly has a reputation for its bitter cold winters, but that doesn’t mean you should spend the next three months hibernating.

We rounded up 31 of our favorite things to do in Chicago this winter. Work your way through our list, and spring will be here before you know it!

Explore world-class museums

1. The Art Institute of Chicago

Located in the heart of downtown Chicago, the Art Institute is considered by many to be one of the best museums in the world. With more than 300,000 works of art, it’s a museum you’ll want to visit again and again.

You may already know that children under 14 get in for free. But now, children between ages 14-17, who are residents of the City of Chicago, get in free, too. If you’re a Chicago or Illinois resident, be sure to take advantage of Free Winter Weekdays. You’ll receive free admission on weekdays from January 9 to February 16, 2017.  These complimentary tickets are issued at the museum admission counter.

Make your trip to the Art Institute even easier by reserving parking in advance. Book Art Institute parking here.


2. The Field Museum

The Field Museum is Chicago’s museum of natural history and is one of the largest in the world. One of the most famous exhibits is SUE the T.Rex,  the largest, best-preserved, and most complete Tyrannosaurus rex ever found.

With Free Admission Days, basic admission is free for Illinois residents with valid proof of residency. The following dates have been released, with more to come:

January 4, 5, 16, 28, 29, 30
February 1 – 28

Reserve Field Museum parking here.


3. The Shedd Aquarium

The Shedd is the largest indoor aquarium in the world! With more than 8,000 aquatic animals, it’s a must-see museum in Chicago. Residents of the City of Chicago receive a $3 discount on admission every day, and Illinois residents get free admission on the following dates this winter:

January 9, 10, 16, 17, 23, 24, 27, 28, 29 30, 31
February 6, 7, 10, 11, 12, 13, 14, 21, 27, 28

Be sure to reserve Shedd Aquarium parking in advance!


4. The Adler Planetarium

The Adler opened to the public in 1930 and is the western hemisphere’s first planetarium. Here are four ways to explore the Adler this winter. Admission is free to Illinois residents on the following dates in January and February:

January 6-13, 16-20
February 6-10, 20-24

Reserve Adler Planetarium parking here.


5. The Museum of Science and Industry

Chicago’s Museum of Science and Industry brings science to life for kids and adults of all ages. It features a bunch of can’t-miss exhibits including a U-505 submarine. Admission is free to Illinois residents on the following dates this winter:

January 10, 11, 12, 16, 17, 18, 19, 24, 25, 26, 31
February 1, 2, 7, 8, 9, 14, 15, 16, 21, 22, 23, 28


6. Lincoln Park Zoo

Located just off Lake Shore Drive in Chicago, the Lincoln Park Zoo is open and free every day. Even in the winter, there’s plenty to see, ranging from polar bear training to free flight feeding. Through February 26, there’s ice-skating at the Zoo on select days.

Reserve Lincoln Park Zoo parking here.


7. Kohl Children’s Museum

The Kohl Children’s Museum is located in Glenview, IL, just north of Chicago. With 17 interactive exhibits, it’s a great way to get kids out of the house this winter. And don’t miss the SpotHero exhibit when you’re there!


Bring the outdoors inside

8. Logan Square Farmers Market

The Logan Square Farmers Market is a summer favorite among Chicagoans, but you can enjoy it in the winter, too! The market runs indoors every Sunday between 10:00 AM – 3:00 PM, from November 6, 2016 until March 26, 2017. Stop by for local produce and seasonal staples.


9. Rock climbing at Brooklyn Boulders

Get your fill of rock climbing right in the heart of Chicago’s West Loop. This indoor climbing facility is ideal for beginners, advanced climbers and everyone in between.

Reserve Brooklyn Boulders Chicago parking here.


10. Indoor skydiving at iFLY Chicago

Ready to try something new this winter? Indoor skydiving at iFLY gives you the feeling of free fall in a safe environment. No parachute or cliff-jumping required.

Reserve parking near iFLY here.


Catch the Bulls and Blackhawks

11. and 12. Grab tickets to the Bulls or Blackhawks and head to the United Center for a sure-fire good time this winter. If you’re not picky about who they’re playing, do some digging to find the cheapest tickets.  Then reserve Chicago Bulls and Blackhawks parking here.


Have a laugh

13. The Second City

The Second City is a world-famous comedy club, known for its always-entertaining shows as well as its famous alums, including Bill Murray, Tina Fey, Amy Poehler, Steve Carell, and Stephen Colbert. You can’t go wrong with any of the shows–just be sure to reserve your tickets far in advance, as shows regularly sell out. Then reserve parking near Second City here.


14. The Comedy Bar

The Comedy Bar, one of Chicago’s top comedy clubs, is located in the heart of River North, making it within walking distance of several downtown hotels. But if you’re driving, we’ve got you covered. You can reserve parking near The Comedy Bar here.


15. Laugh Factory

Chicago’s Laugh Factory is an off-shoot of the original Laugh Factory in Hollywood. World famous comedians have performed here, so if you’re a fan of stand-up, be sure to catch a show here this winter. You can also reserve Laugh Factory parking here.


Take in some tunes

16. The Green Mill

The famous Green Mill is believed to be the oldest continuously run jazz club in the United States. Check out the calendar of upcoming performances and stop by for live jazz or a poetry slam! Then reserve Green Mill parking here.


17. Kingston Mines

Kingston Mines is widely considered to be one of Chicago’s best blues clubs. It features a mix of local bands and world-famous blues artists on a regular basis. Kingston Mines is on a busy stretch of Chicago’s Lincoln Park neighborhood, so do yourself a favor and reserve parking in advance.


18. The Vic

The Vic is one of Chicago’s biggest music venues, featuring a beautiful theater with great acoustics. On its ‘off’ nights from music, The Vic transforms into The Brew & View, a movie theater showing cult favorites and second-run movies for just $5. It is located in Chicago’s bustling Lakeview neighborhood. If you don’t want to circle the block a bunch of times, consider reserving parking in advance.


19. The Chicago Theatre

The Chicago Theatre is a landmark theater located in the heart of downtown Chicago. Upcoming acts include Aretha Franklin, Martina McBride, Wilco, Regina Spektor and more. You could also see a bunch of famous comedians this winter, including Chris Tucker, John Cleese, Sinbad and George Takei. Then reserve Chicago Theatre parking here.


20. Chicago Symphony Orchestra

This January, the Chicago Symphony Orchestra will travel to Europe for an 11-concert tour, but plenty of other performances will fill the Symphony Hall, including A Prairie Home Companion on January 14. The CSO returns to Chicago in early February. Check out the full calendar here, and then reserve parking in advance.


Try something new on the food & drink front

21. The Chopping Block – Merchandise Mart

Channel your inner Julia Child by taking a cooking class at The Chopping Block. Classes in January and February offer a range of cooking styles and cuisines, from a sushi workshop to simple French food. After you’ve reserved your spot at The Chopping Block, make a reservation for nearby parking.


22. Afternoon Tea at The Drake

Believe it or not, Afternoon Tea at The Drake Hotel has been a tradition for nearly a century. When you arrive at the Palm Court, you’ll choose from 17 selections of tea, plus a tier of finger sandwiches, petit fours, English scones and mini lemon poppy seed loaf accompanied by preserves, lemon curd, and English Devon Cream.

You can reserve parking near The Drake here.


Chicago Food Halls:

Chicago has seen an explosion of food marketplaces and halls, especially in the last few years.

23. With over 30 vendors, Chicago French Market is a European-style indoor market with fresh food, flowers and international cuisine. Reserve parking near Chicago French Market here.


24. Eataly is Mario Batali’s sprawling two-story Italian marketplace in the heart of River North. If you find yourself wandering its aisles for hours, you’re not alone. You can reserve Eataly parking here.


25. Revival Food Hall is an all-local outpost in the Loop.  Stop by on a weekday and enjoy staples from some of Chicago’s most popular restaurants, including Aloha Poke, Smoque BBQ, Furious Spoon and many more. You can reserve parking near Revival here.


26. Latinicity is one of the latest additions to Chicago’s food hall scene and offers a twist on Latin street food. It features 10 cafeteria-style restaurants, plus a tapas restaurant, coffee café, full bar, market and lounge. Latinicity is located in a busy area of the Loop, so you may want to book parking in advance.


Solve your way out of an escape room

27. Room Escape Adventures

At Room Escape Adventures, you have 60 minutes to solve puzzles with your team, in order to escape a locked room–while a chained-up zombie inches closer to you and tries to eliminate you from the game. The hour will fly by! You can find and reserve parking near Room Escape Adventures here.


28. Escape Artistry

If zombies aren’t your thing, try The Railcar at Escape Artistry. What begins as a normal commute on the el train soon becomes a race against time. Work with your team to solve puzzles and save the city of Chicago from disaster. You can reserve parking near Escape Artistry here.


29. Fox in a Box

Fox in a Box is another escape room adventure, with four different missions: The Lab, The Bunker, The Bank, and The Prison. Pair up with a partner or some friends and choose your mission! Then reserve parking in advance.


Enter the Hamilton lottery every day

30. Haven’t snagged Hamilton tickets yet? You can enter the lottery every day right here for your chance at $10 tickets. If you get tickets, consider yourself very lucky! Then reserve parking for Hamilton here.


Take a vacation

31. And if you just can’t take the cold anymore, we wouldn’t blame you for heading out of town. If you’re going to the airport, reserve your parking spot in advance!

Parking near O’Hare Airport

Parking near Midway Airport