Best Things to Do in Chicago in the Winter (From a Local!)

The best things to do in Chicago in the winter. You will find something for both adults and families with kids to do in January, February and early March in the city and suburbs.

Things to Do in Chicago in the Winter

Things to do in Chicago in the winter

Winter is officially here in Chicago. Wondering what there is to do in Chicago this winter? Below are the best things to do in Chicago during the winter – whether looking for fun outdoor winter activities or the best indoor attractions.

Go Ice Skating

Skating ribbon at Maggie Daley Park in Chicago

There are several places to go outdoor ice skating in Chicago during the winter. One of the best and picture perfect spots to go ice skating in downtown Chicago is the skating ribbon at Maggie Daley Park which has a path twice the length of a lap around a traditional skating rink.

When:  Open daily (weather permitting) through February 28, 2021. Reservations are required and can be made up to 2 weeks in advance. See the official website for hours and to make a reservation.

Where: 337 E Randolph St., Chicago, IL 60601

Cost:  Skating costs $5 if you bring your own skates. You can rent skates for $16-$20 depending on date.

Go Sledding

Chicago usually gets a lot of snow during the winter. If there is snow on the ground (usually at least 3 inches), grab a sled and head to one of sledding hills found in parks and forest preserves in the Chicago area.

Where: Various. See Best Sledding Hills in Chicago.

Cost:  Free

Get Some Culture at The Field Museum

You can The Field Museum is a natural history museum in Chicago, Illinois, and is one of the largest such museums in the world.

When: Open 9am to 5pm, Thursday through Monday. Closed on Tuesdays and Wednesdays. Must purchase timed tickets to enter.

Where: Chicago’s Museum Campus, 1400 S Lake Shore Dr, Chicago, IL 60605 (detailed directions and parking information is available here)

Cost:  Prices vary. Click here to see prices and purchase tickets online in advance.

Visit the Shedd Aquarium

You can Shedd Aquarium for unforgettable encounters with belugas and bluegills, stingrays and sturgeons.

When: Advance purchase of timed tickets is required.

Where: 1200 S. Lake Shore Drive, Chicago, IL 60605 (detailed directions and parking information is available here)

Cost: Admission is $39.95 ($19.95 for Chicago residents) for adults; $29.95 ($14.95 for Chicago residents) for children (3–11)

Take Fun Photos at the Museum of Illusions Chicago

The new Museum of Illusions Chicago offers an interactive, immersive and fun experience for both adults and kids. Visitors can engage in over 80 astonishing and mind-bending exhibits that will teach you about vision, perception, the human brain and science. The original concept was launched in Zagreb, Croatia in 2015 and has expanded to over over 15 cities around the world.

When: Sunday – Thursday: 10am – 8pm Friday – Saturday: 10am – 9pm

Where: 25 E Washington St, Chicago, IL 60602

Cost:  Adult (ages 18+): $21 Child (ages 5 – 12): $15 Child (ages 4 and under): FREE
Student (ages 13+), Teachers, Military / First responders and Senior Citizens (ages 60+): $18​ with ID
Family (2 adults + 2 children): $65

Enjoy the views from 360 CHICAGO Observation Deck

The 360 CHICAGO Observation Deck on the 94th floor of the former John Hancock Building has the best views of the Chicago skyline and Lake Michigan.

Where: 875 North Michigan Avenue, 94th floor, Chicago, IL 60611

When: Friday – Monday: 9 AM – 9 PM (last entry is 30 minutes prior to closing); Tuesday – Thursday: Closed

Cost:  Adults: $25.00, Youth (3 to 11): $15.00, children (under 3): free. $5 extra for Tilt.

Outdoor Curling

Curling is a winter sport in which players slide stones on a sheet of ice or a lane towards a target. Two Chicago hotels have outdoor curling rinks on their rooftops.

Curling at The Gwen


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The Gwen Hotel, a luxury hotel, has custom-designed, an iceless Curling Rink on its outdoor rooftop terrace. Come on in and experience our Winter Wonderland by curling with the skyline view!

When:  Now through March 14, 2021. See their website to make a reservation.

Where: Upstairs at The Gwen, 521 North Rush Street, Chicago, IL, 60611

Cost:  Admission is $30 per person (for a minimum of 2 people), which includes a choice of one cocktail and 45 minutes of curling play time.

Curling at The Kennedy Rooftop
The Kennedy Rooftop, on top of the new Hyatt Place Wicker Park, also offers outdoor curling with amazing skyline views.

When:  See their website to make a reservation.

Where: The Kennedy Rooftop at Hyatt Place Chicago / Wicker Park, 1551 W North Ave, Chicago, IL 60622

Cost:  $30 non-refundable deposit for 1 hour.

Eat and Drink in an Igloo


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Having dinner and drinks in an outdoor igloo has been trendy for a few years but there are more igloos in Chicago this year. Here are some of the best outdoor igloos in Chicago open this winter (advance reservations are required).

Kennedy Rooftop: 1551 W North Ave, Chicago, IL 60622
Joy District: 112 West Hubbard Street, Chicago, IL 60654
I|O at The Godfrey Hotel Chicago: 127 West Huron Street, Chicago

See the Immersive Van Gogh Exhibit

Chicago will be the setting for the U.S. premiere of Immersive Van Gogh Exhibit, a massive indoor digital presentation of Vincent Van Gogh’s artwork.  From the creators of the blockbuster show at Atelier des Lumières seen by over 2 million visitors in Paris and Toronto and featured in Emily in Paris on Netflix.

When: Opens February 11, 2021. Must purchase tickets online in advance.

Where: Lighthouse ArtSpace at Germania Place, 108 W. Germania Pl, Chicago IL

Cost:  Tickets start at $39.99 plus fees for off peak times. See https://www.vangoghchicago.com/ for full prices and to purchase tickets in advance.

Admire Famous Works of Art at The Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and largest art museums in the United States. The museum has been closed for the last few months but will be reopening February 11, 2021. Two exhibitions, “Monet and Chicago” and “Bisa Butler: Portraits,” will be extended beyond their original closing dates.

When: Hours are Monday and Thursday–Sunday from 11 a.m.– 6 p.m. (10–11 a.m. for members). Closed on Tuesday–Wednesday. Must purchase tickets online in advance.

Where: 111 S Michigan Ave, Chicago, IL 60603

Cost:  $25 for adults, $19 for seniors, students and teens (14-17); members and children under 14 are always free. Visit their website to purchase tickets in advance.

As you can see there are many things to do in Chicago in the winter (even this year). Have you visited Chicago during the winter? If you end up loving Chicago (most people do), you can always return when the weather is warmer for Chicago tourist attractions you can enjoy year round.

Planning a trip to Chicago? Check out my Chicago guides and itineraries:


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