Things to Do in Chicago in Winter 2025 – Chicago in winter transforms into a sparkling wonderland, where frosty winds off Lake Michigan meet twinkling holiday lights and cozy indoor escapes. If you’re searching for things to do in Chicago in winter, you’ve landed in the right place. From November through March, the city blends its iconic architecture with seasonal festivities, offering a mix of outdoor adventures and warm havens. Whether you’re a local dodging the polar vortex or a visitor chasing that “Christmas in Chicago” vibe, 2025 promises lower crowds, festive markets, and unique experiences like igloo dining under the stars.
As temperatures dip into the 20s and 30s Fahrenheit, Chicago’s resilience shines—think heated rooftops, free museum days, and sledding hills with skyline views. This guide curates the top 10 things to do in Chicago this winter, drawing from trusted sources like Choose Chicago, Time Out, and local insiders. We’ve optimized for 2025 events, with tips on bundling up, booking ahead, and making the most of shorter days. Pack layers, waterproof boots, and an appetite for deep-dish pizza—your Windy City winter awaits.
1. Glide on Ice at Millennium Park or Maggie Daley Park Rinks
Nothing screams Chicago winter activities like lacing up skates amid the glow of the city skyline. Millennium Park’s McCormick Tribune Ice Rink, open from mid-November to early March, offers free admission (skate rentals $15-20) with unbeatable views of Cloud Gate (The Bean) dusted in snow. Reserve online to skip lines, and time your visit for evenings when the Christmas tree lights up nearby. For a twist, head to Maggie Daley Park’s Skating Ribbon—a 800-foot winding path through playground sculptures, perfect for families or date nights. It’s twice the length of a standard rink, with penguin aids for kids ($5) and lockers for gear.
In 2025, expect enhanced holiday programming, including DJ nights and hot cocoa stations. Locals swear by weekdays for fewer crowds; arrive early to snag skyline selfies. Pro tip: Pair it with a stroll to the Art Institute for a seamless indoor-outdoor day. This ritual captures Chicago’s blend of urban grit and festive joy, making it a must for first-timers.
2. Wander the Christkindlmarket for European Holiday Cheer
Step into a Bavarian village at the Christkindlmarket, Chicago’s premier winter holiday market running mid-November to Christmas Eve. The original downtown spot at Daley Plaza features 30+ vendors slinging glühwein (mulled wine, $8-10), handmade ornaments, and pretzels amid wooden stalls and a massive Christmas pyramid. In 2025, expect live oompah bands and gingerbread decorating workshops on weekends. For a Cubs twist, hit the Wrigleyville edition at Gallagher Way (free entry, December 7-31), complete with ice skating on Wrigley Field and beer-infused hot chocolate.
Aurora’s suburban market adds family-friendly rides and reindeer visits. Bundle in a scarf—nights drop to 20°F—and sip slowly to savor the spices. This tradition, inspired by Nuremberg’s markets, draws 1.5 million annually, fostering that rare “hygge” in the Midwest chill. Entry is free; budget $20-30 for treats. It’s pure magic for Chicago Christmas things to do.
3. Dive into World-Class Museums with Winter Perks
Winter’s your secret weapon for Chicago museums in winter—fewer lines mean more time with T-Rex Sue at the Field Museum or Monet’s haystacks at the Art Institute. The Field Museum’s “Christmas Around the World” exhibit (mid-November to early January) showcases 50+ international trees, blending culture and holiday spirit. Tickets start at $26; go Wednesday evenings for free entry (donations suggested).
The Museum of Science and Industry dazzles with a holiday train display looping through global villages, while the Shedd Aquarium’s beluga encounters ($10 add-on) feel extra enchanting under dim lights. In 2025, look for extended hours during polar vortex weeks. Insiders recommend the Chicago History Museum for its Great Fire exhibit—pair with hot cider from the cafe. These havens warm souls and bodies, turning blustery days into intellectual feasts. Pro tip: Buy the Go Chicago Explorer Pass ($70+) for multi-site access.
4. Cozy Up at Winter Rooftops and Igloo Bars
Chicago’s winter rooftop bars redefine après-ski with fire pits, domes, and skyline toasts. The LH Rooftop on the Chicago River pops up heated igloos for $150-200 minimum (groups of 4-6), serving s’mores kits and boozy cocoa amid twinkling lights. In River North, I|O Godfrey’s Winter Wonderland domes evoke snow globes, with reservations essential for peak December weekends.
For 2025 flair, Kennedy Rooftop in Wicker Park adds curling lanes to its bubble igloos. Dress in layers—winds whip at 30 mph—and opt for sunset slots to watch the city illuminate. These spots, blending Nordic coziness with Chicago’s cocktail prowess, are ideal for romantic escapes or girls’ nights. Budget $50-75 per person; the views alone justify the chill. It’s a top pick for unique things to do in Chicago winter.
5. Cruise the Frozen River on a Heated Boat Tour
Brave the elements with a Chicago winter boat cruise, where glass-enclosed vessels let you toast the skyline without frostbite. Wendella Tours’ architecture cruises (90 minutes, $50) hug the Chicago River, narrating Frank Lloyd Wright gems under holiday lights—perfect for December evenings. Chicago Boat Company’s hot tub boats ($300 for 6, BYOB) fit under low bridges, bubbling warmth on the Riverwalk.
Lake Michigan dinner cruises from Navy Pier offer plated meals and live jazz ($100+), with outdoor decks for brave souls. In 2025, expect solstice specials with mulled wine. Book heated options; winds off the lake hit 40 mph. This perspective flips Chicago’s “windy” rep into wonder, highlighting why it’s a bucket-list winter activity in Chicago.
6. Glow at ZooLights: Lincoln Park Zoo After Dark
Lincoln Park Zoo’s ZooLights (November 22, 2025-January 12, 2026) turns 35 acres into a 3.5 million-light spectacle, free Mondays and $15 other nights. Wander paths past illuminated penguins and red pandas, with s’mores stations ($5) and carousel rides. Adults-only Holidaze nights (December 11, $26) add DJ sets and Grey Goose pop-ups.
In 2025, new features include interactive light tunnels and Santa photos. The zoo stays open year-round (free entry), letting you spot snow leopards mid-day before dusk magic. Bundle for 20°F nights; transit via the Red Line. This family favorite embodies Chicago holiday lights, blending wildlife whimsy with festive fire pits.
7. Thrill on Sledding Hills and Snowshoe Trails
When snow falls (aim for 3+ inches), Chicago’s parks become playgrounds for winter outdoor sports. Soldier Field’s 220-foot sledding hill offers Lake Michigan thrills—rent tubes onsite ($10/hour). Humboldt Park’s unofficial slopes suit locals, but check city alerts for safety.
Venture to Morton Arboretum (January-March, $15 entry + $20 rentals) for 9 miles of snowshoe trails through frosted oaks. In 2025, guided Nordic ski tours launch mid-January. Starved Rock State Park (1.5 hours south) boasts frozen waterfalls via heated shuttle hikes ($20). Gear up with thermals; post-sled cocoa at nearby cafes. These adrenaline rushes counter winter blues, proving Chicago’s parks shine in snow.
8. Cheer On the Bulls or Blackhawks at United Center
Fuel your winter with Chicago sports in winter—the United Center pulses with Bulls NBA games (tickets $50+) and Blackhawks NHL clashes through April. Tailgate in heated lots with deep-dish and team chants, even at Soldier Field’s Bears games (if playoffs extend). In 2025, holiday matchups like December 23 Bulls vs. Knicks promise packed energy.
Dress in layers under jerseys; arena temps hover at 65°F. For families, add pre-game clinics. This communal roar melts any freeze, embodying Chicago’s blue-collar heart. It’s not just a game—it’s a warm huddle against the cold.
9. Stroll the Magnificent Mile and Holiday Light Displays
The Mag Mile’s 200-block glow-up, from November to January, features State Street’s twinkling arches and Michigan Avenue’s 1 million lights. Free self-guided walks pass the Walnut Room at Macy’s for tree-trimmed lunches ($30+). In 2025, add the Chicago Christmas Tree lighting (November 28) at Millennium Park.
Extend to Navy Pier’s Winter WonderFest (indoor carnival, $20) or Brookfield Zoo’s Holiday Magic (3.5 million lights, through January 4). Layer against gusts; end with Garrett Popcorn. This promenade captures Chicago winter lights, a shopper’s and sightseer’s dream.
10. Sip and Savor at Themed Pop-Up Bars and Holiday Shows
Chicago’s pop-ups are winter’s cocktail hour: Frosty’s Christmas Bar overflows with decor and eggnog martinis ($15), while Santa Baby’s multi-level setup (December 7-January 4) nails photo ops. In 2025, Jack Frost’s adds bumper cars and tree sales.
Catch “A Christmas Carol” at Goodman Theatre ($50+) or Cirque du Soleil’s ‘Twas the Night Before (tickets from $75). These escapes—laughs, lights, libations—thaw the soul. Reserve ahead; pair with improv at Second City for laughs. It’s the ultimate festive things to do in Chicago December.
Why Chicago Winter 2025 Is Unmissable?
From skating under The Bean to curling in igloos, Chicago’s winter weaves resilience with revelry. With events like Christkindlmarket and ZooLights peaking in December, plan around holidays for peak magic—book via apps like Choose Chicago. Budget $200-300/day for couples, less for freebies. Monitor weather via NOAA; transit’s CTA holiday trains add cheer.
Whether chasing lights or culture, the Windy City proves winter’s for the bold. Ready to book? Dive in—your frosty adventure starts now