Winter turns Chicago into a beautiful wonderland, with snow adding extra charm to the city. Enjoy the season by going ice skating near Cloud Gate (also known as “The Bean”) or sledding by the snowy lakefront. There are plenty of fun and cozy ways to experience and love winter in Chicago.
Go Ice Skating at a Unique Rink
Want to enjoy winter in true Chicago style? Head to the famous ice rink in Millennium Park — it’s a must-visit spot for skating. As you glide across the ice, you’ll be treated to stunning winter views of Michigan Avenue, the city skyline and The Bean covered in snow.
Right next door, you can lace up your skates and glide through the beautiful Skating Ribbon at Maggie Daley Park. This curvy ice path winds through a winter scene filled with pine trees and even passes a rock climbing wall. It’s about twice as long as a regular skating rink, making it a fun and unique place to skate.
You can rent skates at both rinks. They usually stay open from November until early March, depending on the weather.
In Hyde Park, you can visit the Midway Plaisance Ice Rink located on the University of Chicago’s beautiful campus. Interesting fact — this rink sits right where the very first Ferris wheel was built for the 1893 World’s Fair.
Don’t forget to check out the Sky Rink at The Peninsula — it’s the only rooftop ice skating rink in Chicago. You can skate high above Michigan Avenue while enjoying the city views and the lively atmosphere below.
Sip Cocktails on a Winter Rooftop
Stay warm while enjoying Chicago’s popular bar and restaurant scene this winter, with cozy fire pits, heated igloos and plenty of warm outdoor dining spots to choose from.
Places like I|O Godfrey in River North and The Kennedy in Wicker Park set up special winter pop-ups with festive decorations, sparkling lights and private igloos that feel like you’re inside a magical snow globe. Be sure to book a spot at these cozy winter rooftops.
Enjoy Cocktails and Curling
Go up to the lovely rooftop curling rink at The Gwen in River North. This hotel’s rooftop bar has an iceless curling area where you can play the game while sipping winter drinks like spiked hot chocolate. The terrace also has fire pits, perfect for warming up between games.
In the West Loop, Kaiser Tiger is famous for its lively beer garden with bocce courts in summer that turn into curling rinks during winter. The outdoor beer garden has infrared heaters to keep you warm between games, along with a full bar and hot drinks to enjoy.
Get Out on the Water
Winter offers exciting new ways to enjoy Chicago’s beautiful waterfront. You can rent a hot tub boat from the Chicago Boat Company and cruise along the Chicago River. These unique BYOB boats hold up to six people and let you take in the city’s skyline even in the cold months. The company also offers heated duffy boats for a warm and cozy ride.
For a memorable night, try one of the dinner cruises on Lake Michigan. These beautiful boats offer delicious meals, live music, dancing and amazing views of Chicago’s glowing skyline. You can also enjoy a dinner cruise on a glass-enclosed boat along the Chicago River.
Go Sledding, Snowshoeing and Winter Walking
Set on the parkland surrounding historic Soldier Field, home of the Chicago Bears, the Soldier Field sledding hill has a slope that stretches over 200 feet on a tall hill — perfect for thrill-seeking sledders. From the top, you’ll get an unbeatable panoramic view of Lake Michigan.
Just outside Chicago, the Morton Arboretum is a quiet and relaxing spot for winter walks. Visitors can bring their own cross-country skis or snowshoes and rentals are also available there.
Don’t miss the free Polar Adventure Days at Big Marsh Park, where visitors can enjoy making winter crafts inspired by nature, watch husky sled teams in action and see wolves and birds of prey up close.
Visit a Museum
Chicago is full of amazing museums and cultural spots, and they’re the perfect places to stay warm on a cold winter day.
A great place to begin is the lakefront Museum Campus, which is home to famous attractions like the Field Museum, Adler Planetarium and Shedd Aquarium.
Also near downtown, you’ll find the Art Institute of Chicago — one of the oldest and largest art museums in the country.
Visit Museum Campus South to explore the hands-on exhibits at the Griffin Museum of Science and Industry. You can also venture into Chicago’s neighborhoods to find many cultural museums, local art galleries and other hidden gems worth exploring.
Catch a Must-See Winter Show
Winter is the perfect time to explore Chicago’s vibrant theatre scene. Check out Broadway in Chicago for touring shows, hit musicals and pre-Broadway premieres at the city’s historic downtown theatres. You can also enjoy original productions at award-winning theatres like Steppenwolf, Goodman and Court Theatre. For something unique, visit one of the many neighborhood theatres around the city.
Meet the Cold-Weather Zoo Animals
Chicago’s free Lincoln Park Zoo is open all year round. During winter, you can see polar bears, penguins and snow monkeys enjoying the cold weather outside. Many animals stay indoors when it’s chilly, so you can step inside the animal houses to watch penguins, gorillas, bright-colored birds and more.
Visit a Stunning Indoor Garden
Step inside and warm up at one of Chicago’s beautiful indoor gardens or conservatories. The Lincoln Park Conservatory, located in historic Lincoln Park, is free to visit and features several rooms filled with exotic plants and colorful flowers.
Don’t miss the historic Garfield Park Conservatory, one of the biggest in the country, covering two acres of beautiful greenhouse space. You can also find many other indoor gardens to explore in and around Chicago.
Warm Up with Hot Cocoa
Chicago has lots of great places to enjoy a cup of hot chocolate. Visit Katherine Anne Confections for rich drinking chocolate or try Mexican hot chocolate at Kristoffer’s Café & Bakery in Pilsen or XOCO in River North. And don’t miss the creative, picture-perfect cups at BomboBar, a popular walk-up spot in the West Loop.
Admire the Frozen Lake
One of the most amazing sights in winter is when Lake Michigan freezes, creating stunning views. Walk along the Lakefront Trail for a close-up look and great photos of the skyline. You can also stop by nearby attractions, such as The Magnificent Mile for shopping or museums like the Peggy Notebaert Nature Museum, Adler Planetarium and the Griffin Museum of Science and Industry, to warm up before continuing your winter adventure.
Free Things to Do in Chicago in Winter
- Go ice skating at Millennium Park
- Go sledding at Soldier Field
- Join the free Polar Adventure Days at Northerly Island
- Explore Millennium Park
- Walk along the Lakefront Trail
- Visit Lincoln Park Zoo
- Stop by an indoor botanic garden
Outdoor Things to Do in Chicago in Winter
- Go ice skating at Millennium Park
- Skate along the Ribbon at Maggie Daley Park
- Try curling on a rooftop or outdoor rink
- Join the Polar Adventure Days at Northerly Island
- Visit Lincoln Park Zoo
- Explore Millennium Park
- Walk or bike along the Lakefront Trail
- Rent a hot tub boat on the Chicago River
- Enjoy a dinner cruise on Lake Michigan
Indoor Things to Do in Chicago in Winter
- Enjoy cocktails at a cozy winter rooftop bar
- Treat yourself to a cup of hot chocolate
- Visit an indoor garden or conservatory
- Explore museums and art galleries
- Visit famous Chicago attractions
- Watch a live theatre performance
- Have a laugh at The Second City comedy show
- Support the Chicago Bears, Bulls or Blackhawks
Moving Around Chicago in Winter
Getting around Chicago in winter is manageable once you know your options. The city’s public transportation system, including CTA trains and buses, operates reliably even during snow or cold weather. For extra comfort, taxis and rideshare services such as Uber and Lyft are available across the city.
Winter is also a busy season for people relocating to new homes or neighborhoods. STI Moving & Storage, a trusted moving company in Chicago, ensures moves are handled smoothly and safely, even in challenging winter conditions. With proper planning and professional help, moving during the colder months can still be efficient and stress-free.
For shorter trips, walking remains popular since most sidewalks are cleared regularly. Divvy bikes, including electric options, are also available year-round for quick rides. Whether you’re exploring Chicago downtown or settling into a new place, Chicago keeps moving through every season.
Ready to make your move this winter?
Let STI Moving & Storage handle the heavy lifting while you enjoy everything Chicago has to offer.
