This winter is predicted to bring colder and snowier conditions to Chicago than anything we’ve seen in recent years. Winter in Chicago can be a grueling time, but it doesn’t have to be all about snow shoveling and biting temperatures! From sipping mulled “Glühwein” in Daley Plaza 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. A winter Sip & Create Workshop Series
It is one of the essential winter activities in Chicago to cure your January blues! Brought by The Pendry and Venteux Brasserie, the Sip & Create workshops series encourages local residents to explore their creative side. For six weekends from January to March 2025, Chicago-based creatives will teach workshops that include learning the craft of natural dyeing using botanicals and kitchen scraps, jewelry making, inlay clay carving, and beyond.
5. Enjoy a rooftop curling and cocktails experience
The Gwen Hotel’s annual Curling & Cocktails experience is back on November 23, coinciding with the nearby Magnificent Mile Lights Festival.
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.
6. 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.
7. 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.
Don’t miss the “Unseen Oceans” exhibit at the Field Museum, where you can explore the underwater world through life-sized projections and interactive displays.
Art enthusiasts will want to check out artist Jitish Kallat’s ongoing exhibition Public Message 3, which explores the parallels between two historical events within the context of universal peace.
8. 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.
9. 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.
The company has also introduce heated Duffy boats that can accommodate larger groups.
10. Celebrate the start of the holiday season with Chicago’s annual Christmas tree lighting
Chicago’s annual tree lighting celebration is Friday, November 22, at Millennium Park. The event is a beloved tradition in Chicago, marking the unofficial start of the Christmas season.
This year’s celebration will feature live musical performances, followed by the tree illumination and fireworks.
There’s plenty of other fun-filled activities to partake in at Millennium Park this holiday season. On November 15, the McCormick Ice Skating rink will open, followed by the The Millennium Park Holiday Market and the park’s Holiday Sing-Along series.
11. Shop and sip mulled wine at the Christkindlmarket
Another beloved Chicago tradition, the Christkindlmarket will open again this month. Visitors can enjoy German-inspired food vendors, handmade gift options, and of course, festive mulled wine in one of the market’s iconic souvenir mugs.
With so much to do and see, the Christkindlmarket is the perfect winter activity in Chicago with family and friends in the lead-up to Christmas.
Chirstkindlmarket takes place at Daley Plaza in the Loop, and will be open every weekend from November 22-December 24. Click here for more information about dates and time.
12. Catch the CTA holiday train
All aboard the CTA holiday train! Santa’s holiday train trip around Chicago is one of Chicago’s essential winter bucket list activities, and you won’t want to miss it this year.
Beginning in late November, a decked out CTA train will make its rounds along the city’s L system, spreading holiday cheer to all who enter. The CTA holiday train features festive decorations, lights, and holiday music.
A ride along the holiday train is enough to brighten anyone’s day and make the morning or evening commute a fun-filled experience.
In addition to spreading joy as Santa and his reindeer whizz around all eight lines, the Holiday Fleet also delivers donated food baskets to local community organizations and charities.
13. Check out a light show
Experience the magic of the Chirstmas season with one of the many spectacular holiday light shows in Chicago.
From parades, to immersive walk throughs, each light show offers a new unique experience, creating magical holiday memories for visitors of all ages.
14. 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.
15. Indulge at one of Chicago’s holiday pop-ups
If there’s one time of the year to treat yourself, it’s Christmas, and there’s no better place to indulge than at one of the many holiday pop-ups in Chicago.
During the holiday season, bars and restaurants across Chicago decorate themselves head to toe in extravagant holiday decor and offer special Christmas-themed cocktails, boozy milkshakes, and other festive treats. One of the best winter activities in Chicago: stay tuned for our list of the best holiday pop-ups in Chicago for 2025!