Winter in Chicago can be a grueling time, but it doesn’t have to be all about snow shoveling and biting temperatures! From catching a ride on a hot tub boat to gliding around the quarter-mile ice rink in Maggie Daley Park, here’s our winter bucket list and favorite winter activities in Chicago.
1. Go ice skating at the Maggie Daley Ice Ribbon
There’s no better way to glide into winter than with ice skating, and the Maggie Daley Ice Ribbon just might be one of the best ice skating rinks in Chicago!
The winding ribbon of ice curves up and down around a 40-foot climbing wall with the city’s stunning skyline in the backdrop. It’s a must for your winter bucket list. It’s also free Monday-Thursday if you bring your own skates!
2. Let world-class acrobats shock and astound you at Love Struck by AirOtic
If you’re looking to add some heat to your winter, Love Struck by AirOtic Soirée is hosting a series of steamy Valentine’s Day-themed performances. Complete with incredible choreography, seductive stunts, and complimentary cocktails, the seasonal shows are bound to have you on the edge of your seat all evening. Grab tickets here!
3. Dine and Drink in a personal snow globe
Outdoor dining in Chicago doesn’t stop when the temperatures drop. Diners can enjoy the patio experience all winter long at the best igloo dining spots in Chicago.
Igloo dining offers a cozy retreat from the cold while still allowing guests to enjoy stunning views and outdoor ambiance.
From riverside domes at City Winery to rooftop winter wonderlands at the Godfrey Hotel, there are options to suit every taste. Many venues offer special packages, themed decor, and seasonal menus to enhance the magical atmosphere.
4. Enjoy a rooftop curling and cocktails experience
The Gwen Hotel’s annual Curling & Cocktails experience is back!
The rooftop activity combines the Scottish sport of curling with skyline views, making it perfect for winter socializing.
Up to 12 guests can enjoy 50 minutes of curling on an artificial 8′ x 32′ rink, complete with complimentary cocktails and bites. Remember to dress warmly for this outdoor experience.
5. Take a snow tubing trip near Chicago
The Windy City’s flat landscape doesn’t exactly lend itself to sledding, but luckily, there’s no shortage of places for sledding and snow tubing just outside the Windy City.
Chicagoans can take a day trip to Wisconsin and visit the 900-foot-long chute at Cascade Mountain or the Wilmot Mountain Ski Resort. For an adventure closer to home, there’s the 800-foot ride at the Blackwell Forest Preserve in suburban Warrenville.
Unlike skiing, tubing requires little to no experience, making it an easily accessible and fun-filled family activity during the cold months.
6. Browse a world-class museum for free
Whether you’re an animal lover or a contemporary art connoisseur, you can find the perfect exhibit to suit your interests at one of Chicago’s world-class museums this winter.
Illinois residents can take advantage of 2026 free admission days at the Field Museum, Art Institute, Shedd Aquarium, and more this winter.
7. Warm-up and revitalize at one Chicago’s luxurious spas
Treat yourself to a day of relaxation this winter at one of Chicago’s luxury spas. Whether you’re looking for a quick escape or a full day of pampering, Chicago’s spa scene has you covered.
For any interested spa goers, Aire Ancient Baths is a must-try experience.
The hot tub spa features seven different baths at various temperatures where guests can soak and relax. Guests can also enjoy a salt exfoliation area, fresh cucumber water, aroma therapy, and relaxing massages during their stay.
Other ca n’t-miss experiences include the Peninsula Hotel’s spa, the Chuan Spa at the Langham Hotel, and the one-of-a-kind Piva Beer Spa.
8. Sail the Chicago River in a Hot Tub Boat
The Chicago Electric Boat Company’s viral hot tub boats are back this winter season! If you missed out last year, now’s your chance to get in on all the fun.
One of our favorite winter activities in Chicago, the unique zero-emissions vessels feature a fully functioning hot tub that can accommodate up to six people.
These boats offer a perfect blend of relaxation and sightseeing, equipped with underwater lights, floating cup holders, and a bluetooth speaker.
9. Rent a Private Sauna Pod
Local company Thunder Domes has launched their Fire and Ice Sauna pod at North Avenue Beach just in time for winter.
The mobile, wood-fired sauna offers customizable temperatures between 160 and 200 degrees, perfect for warming up during chilly Chicago winters.
Visitors can enjoy 25-minute to one-hour sessions, with the option to take an invigorating plunge in the icy lake waters.
The sauna pod accommodates up to three guests, making it one of the ideal fun outings with friends and winter activities in Chicago.
