Winter is one of the most magical times of the year in Chicago, when snow gives the city an added sparkle. Embrace the season and set off on a wintry adventure, from ice skating in the shadow of Cloud Gate (aka “The Bean”) to sledding within view of the snowy lakefront. You’ll find lots of reasons to love winter in Chicago.
- Free things to do in Chicago in winter
- Outdoor things to do in Chicago in winter
- Indoor things to do in Chicago in winter
Go ice skating at a unique rink
Looking for the ultimate winter experience in Chicago? The iconic rink in Millennium Park is a bucket-list spot to take a spin on the ice. You’ll be surrounded by breathtaking winter views of Chicago, including bustling Michigan Avenue, the downtown skyline, and The Bean dusted in snow.
Nearby, strap on a pair of skates and glide through a winter wonderland along the curvy Skating Ribbon that meanders through scenic Maggie Daley Park. The winding path, which is twice the length of a lap around a traditional skating rink, passes by pine trees and a rock climbing wall.
Skates are available to rent at both rinks. These rinks are open from November through early March, weather permitting.
In Hyde Park, head to the Midway Plaisance Ice Rink on the gothic University of Chicago campus. Fun fact: The rink stands on the exact spot where the first-ever Ferris wheel was erected for the 1893 World’s Fair.
And don’t miss the Sky Rinkat The Peninsula, the only rooftop ice skating rink in the city, perched high above the hustle and bustle of Michigan Avenue.
Explore more: Check out more winter ice rinks around Chicago.
Sip cocktails on a winter rooftop
Stay warm while enjoying Chicago’s acclaimed bar and restaurant scene with cozy fire pits, toasty igloos, and more heated outdoor dining options this winter.
Unique spots like the I|O Godfrey in River North and The Kennedy in Wicker Park host seasonal pop-ups with festive decor, twinkling lights, and personal igloos that make you feel like you’re in an enchanted snow globe. Grab a reservation at these cozy winter rooftops.
Enjoy cocktails and curling
Head upstairs to the charming curling rink at The Gwen in River North. The hotel’s rooftop bar features an iceless curling rink, where you can play this classic winter sport while enjoying seasonal cocktails like boozy hot chocolate. The rooftop terrace is also decked out with fire pits so you can cozy up between rounds.
In the West Loop neighborhood, Kaiser Tiger is known for its bustling beer garden with bocce courts in the summer, which transforms into outdoor curling rinks in the winter. The cold-weather beer garden features infrared heaters to keep you cozy between rounds, plus a full bar and warm cocktails.
Get out on the water
Winter brings fun new ways to explore Chicago’s stunning waterfronts. On the Chicago River, rent a hot tub boat from Chicago Boat Company. These one-a-kind BYOB vessels fit six people and are a unique way to admire the city’s skyscraper-lined Riverwalk in the colder months. The company also rents heated duffy boats.
For an unforgettable evening, check out the many dinner cruises on Lake Michigan. These luxurious vessels offer elegant plated meals, live music and dancing, and breathtaking views of the sparkling Chicago skyline. You can also opt for a dinner cruise on a glass-enclosed boat on the Chicago River.
Go sledding, snowshoeing, and winter walking 
Located on parkland surrounding historic Soldier Field (home of Chicago Bears football), the Soldier Field sledding hill features a slope spanning more than 200 feet on a towering hill that makes it a must for thrill-seeking sledders. And the panoramic view of Lake Michigan from the top can’t be beat.
Just outside Chicago, the Morton Arboretum offers a peaceful place for winter walks. Guests are welcome to bring their own cross-country skis or snowshoes and rentals are available on site.
And don’t miss the free Polar Adventure Days at Big Marsh Park, when visitors can make nature-inspired winter crafts, watch husky sled teams at work, and encounter wolves and birds of prey.
Explore more: Find more things to do in Chicago all year round.
Visit a museum
There’s no shortage of acclaimed cultural institutions in Chicago — and all of them are a great place to warm up during a chilly winter day.
A good place to start is the lakefront Museum Campus, home to iconic spots like the Field Museum, Adler Planetarium, and the Shedd Aquarium.
Also near downtown, you’ll find the Art Institute of Chicago — one of the country’s oldest and largest art museums.
Head to Museum Campus South to explore the interactive Griffin Museum of Science and Industry. Or head out into the city’s neighborhoods to discover a treasure trove of cultural heritage museums, art galleries, and other hidden gems.
Catch a must-see winter show
Winter is a great time to discover the city’s diverse theatre scenes. Check out what’s playing from Broadway in Chicago, which brings touring productions, hit musicals, and pre-Broadway premieres to Chicago’s historic downtown theatre district. Or see an original production staged at the city’s many Tony Award-winning theatre companies, like the Steppenwolf Theatre, the Goodman Theatre, Court Theatre, and more. If you’re looking for something one of a kind, you’ll love the city’s many neighborhood theatres.
Meet the cold-weather zoo animals
Chicago’s free Lincoln Park Zoo is open for exploration 365 days a year. In the colder months, admire majestic polar bears, penguins, and snow monkeys as they play outside. Many of the animals move indoors during the winter, so warm up inside the animal houses, where you can watch penguins, gorillas, colorful birds, and more.
Visit a stunning indoor garden
Get inside and warm up at one of Chicago’s indoor botanic gardens and conservatories. The Lincoln Park Conservatory is a free experience in historic Lincoln Park, with multiple rooms dedicated to exotic flora and flowers.
And don’t miss the historic Garfield Park Conservatory, one of the largest conservatories in the nation, occupying two acres of lush greenhouse space. Find more indoor gardens to explore in and around Chicago.
Warm up with hot cocoa
Chicago has plenty of spots to indulge in a cup of cocoa. Head to Katherine Anne Confections to try the decadent drinking chocolate, or try a mug of Mexican hot chocolate from Kristoffer’s Café & Bakery in Pilsen or XOCO in River North. And don’t miss the over-the-top, Instagram-worthy cups at BomboBar, a popular walk-up window in the West Loop.
Explore more: Check out more of the top spots for hot chocolate in Chicago.
Admire the frozen lake
One of the best things about the chilly weather? When Lake Michigan freezes over and makes for some epic views. Head to the Lakefront Trail for an up-close look and a picture-perfect angle of the skyline. Plus, you can easily experience some of the city’s best shopping destinations (like The Magnificent Mile) and cool museums (like the Peggy Notebaert Nature Museum, the Adler Planetarium, or the Griffin Museum of Science and Industry) to warm up before you continue your winter exploration.
Free things to do in Chicago in winter
- Ice skating at Millennium Park
- Sledding at Soldier Field
- Experience Polar Adventure Days at Northerly Island
- Explore Millennium Park
- Walk the Lakefront Trail
- Go to Lincoln Park Zoo
- Visit an indoor botanic garden
Outdoor things to do in Chicago in winter
- Ice skating at Millennium Park
- Skate the Ribbon at Maggie Daley Park
- Go curling on a rooftop or outdoors
- Experience Polar Adventure Days at Northerly Island
- Go to Lincoln Park Zoo
- Explore Millennium Park
- Walk the Lakefront Trail
- Rent a hot tub boat on the Chicago River
- Take a dinner cruise on the lake
