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 December, January, February and early March in the city and suburbs.

Things to do in Chicago in the winter

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Where to Stay in Chicago During the Winter

If you are visiting Chicago in the winter, it is even more important to stay somewhere centrally located so you don’t have to walk very far while sightseeing or spend money on ride sharing. I recommend these Chicago hotels for winter – they are not only centrally located but many also offer winter attractions and activities like heated rooftops and even curling.

The Peninsula Chicago.  The Peninsula Chicago is a 5 star hotel with a central and convenient location right off the Magnificent Mile, close to shopping and less than a block from the Water Tower and 360 Chicago. This is the only hotel in Chicago with a seasonal skating rink. Other hotel amenities include a world renown spa and a half-Olympic length swimming pool. Click here to see the latest prices and click here to read reviews.

Gwen Hotel Chicago.  The Gwen Hotel Chicago is conveniently located off the Magnificent Mile and is connected to The Shops at North Bridge, which provides guests with enclosed access to shopping. The hotel was ranked #1 in Chicago and #8 in the world according to Condé Nast The Best Hotels in the World: 2021 Readers’ Choice Awards. It has an outdoor winter rooftop with fire pits and heaters as well as outdoor curling and igloos. Click here to see the latest prices and click here to read reviews.

LondonHouse Chicago, Curio Collection by Hilton.  LondonHouse Chicago, Curio Collection by Hilton is located on the iconic Chicago River, on the corner of Wacker Drive and Michigan Avenue, just minutes away from Millennium Park and the city’s theater and business districts. Many or their rooms as well as their tri-level rooftop bar have amazing views of the Chicago River. Click here to see the latest prices and click here to read reviews.

Chicago Athletic Association Hotel.  Chicago Athletic Association Hotel is a unique boutique hotel conveniently located right across The Bean and Millennium Park. It is a short walking distance to two ice skating rinks as well as The Art Institute of Chicago. The hotel has several bars & restaurants including Cindy’s, the popular rooftop restaurant and bar which offers panoramic instagram worthy views of Millennium Park and Lake Michigan. Families will enjoy spending time in their Game room where you can play billiards, shuffleboard, foosball, and other games for free. Click here to see the latest prices and click here to read reviews.

What to Pack for Chicago in the Winter

For out of town visitors, winter in Chicago is typically very cold and it frequently snows. Layers are key because the temperature can vary greatly (from below zero to more than 60 Fahrenheit). Here are some things to pack if you are visiting Chicago in the winter for the first time:

• Winter coat – I recommend a longer coat with a hoodie to keep you warm
• Knit hat
• Scarf
• Gloves – Thin touchscreen gloves are best so you can use your smartphone without having to take them off
• Boots – Boots are a must if it snows but some people like to wear them even if there is no snow because they are warmer. Make sure your boots are water resistant with good traction.
Reusable water bottle
External battery for your phone – To recharge your phone’s battery when you are outdoors

Things to Do in Chicago in the Winter

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 Chicago indoor attractions.

See the City of Chicago Christmas Tree

Seeing the City of Chicago Christmas Tree

The City of Chicago puts up a large Christmas Tree annually at Millennium Park during the holiday season.

The Bean in Chicago's Millennium Park with the Christmas tree in the background

Make sure to stop by The Bean – a must on any Chicago bucket list. The Bean is located a few feet away from the tree and can even take photos of The Bean with the Christmas tree in the background.

Where: Millennium Park near the intersection of Michigan Avenue & Washington Street.

Cost:  Free.

RELATED: Best Places to See Holiday Lights in Chicago for more places to see holiday lights in Chicago and the suburbs this winter.

Go Outdoor Ice Skating

Outdoor Ice Skating in Chicago in the winter

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 is at the McCormick Tribune Ice Rink in Millennium Park right in front of The Bean. Admission is free, but online ticketed reservations are required. Reservation dates are released 2 weeks in advance.

Skating ribbon at Maggie Daley Park in Chicago

Another ice skating rink with great skyline views is the skating ribbon at Maggie Daley Park located next to Millennium Park. The skating ribbon has a path twice the length of a lap around a traditional skating rink.  Reservations are strongly encouraged.  See the official website for hours and prices.

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

Polar Adventure Days at Northerly Island

Have fun this winter while enjoying all the wonders of nature at the annual Polar Adventure Days at Northerly Island. This family friendly event is offered two Saturdays throughout the winter and is free. All activities will be outdoors.

Activities include: touring the new Northerly Island Natural Area during winter, seeing Husky teams sled around the peninsula, encountering birds of prey, making nature-inspired winter craft, building a shelter in the Nature Play space, toasting a marshmallow over a camp¬fire and exploring the island on snowshoes (if there’s snow).

Where: Northerly Island, 1521 S. Linn White Drive, on the Museum Campus.

Cost: FREE but registration required. Limited parking is available for $3, cash only, during Polar Adventure Days.

Go Snowtrekking at Northerly Island

At least three inches of snow on the ground, explore Northerly Island and Burnham Nature Sanctuary on snowshoes in the winter while enjoying incredible views of Chicago and looking out for winter birds and various wildlife.

Snowshoes are provided for all participants (registration is required) on select Saturday mornings in January and February (weather permitting).  Call (312) 745.2910 to verify weather conditions before you go.

Cost:  $5 to check out a pair of snowshoes with a valid ID.

Drive Ice Bumper Cars at Gallagher Way

The Rink at Gallagher Way is back with an 8,000-square-foot ice rink for skaters of all skill levels to skate on their own, participate in skating lessons and learn to curl.

Hours: Monday through Thursday from 5-9 p.m., Saturdays from 5-9 p.m. and Sundays from 3-7 p.m. Closed Fridays.

Cost: $15 for a 10-minute ride.

Where: Gallagher Way, 3635 N Clark St, Chicago, IL 60613

Go Outdoor Curling

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A post shared by The Gwen Hotel (@thegwenchicago)

Curling is a winter sport in which players slide stones on a sheet of ice or a lane towards a target. Below is a list of places offering outdoor curling (along with drinks) this winter:

Upstairs at The Gwen, 521 North Rush Street
Kennedy Rooftop, 1551 W North Ave
Harry Caray’s Tavern – Navy Pier, 700 E. Grand Ave

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. Here are some of the best outdoor igloos in Chicago open this winter (advance reservations may be required).

Kennedy Rooftop (1551 W North Ave)
I|O at The Godfrey Hotel Chicago (127 West Huron Street)
Joy District (112 West Hubbard Street)

Enjoy Warm Temperatures at the Garfield Park Conservatory

The Garfield Park Conservatory is one of the largest and most stunning botanical conservatories in the US. Often referred to as “landscape art under glass,” the Garfield Park Conservatory showcases thousands of plant species from around the world throughout eight indoor display gardens.  

Where: 300 N. Central Park Ave., Chicago, IL 60624

Hours: Wednesday 10am-8pm; Thursday – Sunday 10am-5pm; Closed Monday and Tuesday. Visitors are encouraged to make a reservation online in advance.

Cost: FREE (suggested donation)

See Flowers inside the Lincoln Park Conservatory

Lincoln Park Conservatory is always green and lush year round, offering visitors a tropical experience within its four display houses: Palm House, Fern Room, Orchid House and Show House.

Hours: Timed entry reservation is required.

Where: 2391 N. Stockton Drive, Chicago, IL 60614

Cost: Free.

Visit the Field Museum

The Field Museum is one of the largest natural history museums in the world with more than 40 million specimens and artifacts. Inside the museum you will see Maximo, the Titanosaur, the largest dinosaur that ever lived. (Click here to purchase an Early Access VIP Tour if you want to avoid crowds).

Hours: Open daily 9am to 5pm (last admission at 4pm)

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

Cost:  Prices vary. 

Admire Famous Works at The Art Institute of Chicago

The Art Institute of Chicago
The Art Institute of Chicago is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. (Click here to buy a skip the line ticket if you want to avoid long lines).

When: Hours are Monday and Thursday–Sunday from 11 a.m.– 6 p.m. Closed on Tuesdays & Wednesdays.

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 the Shedd Aquarium

Visit the Shedd Aquarium is one of the best and most visited aquariums in the United States.  

When: Open 9am to 6pm daily. 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)

Tip:  If you are visiting a few museums and indoor attractions, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.

READ: Best Indoor Things to Do in Chicago for more indoor Chicago attractions.

See the Orchid Show at Chicago Botanic Garden

Soak up the color and fresh blooms of thousands of orchids and other tropical plants at the Chicago Botanic Garden. This year’s Orchid Show: Untamed celebrates the unexpected verve of wild orchids. See what happens when sweeps of orchids take over an old secret garden, twine around abandoned pillars, and break through the whimsical spaces of our imagination.

Where: Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe, IL 60022 (24 miles north of downtown Chicago)

Cost: Adult: $7 Member/non-Member $9; Children (3-12): $5 Member/$6 non-Member; Children 2 and under are free. Orchid Show ticket includes admission to the Garden; $8 parking fee applies. See for prices and to purchase tickets.

As you can see there are many things to do in Chicago in the winter. 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: