The best November 2025 events in Chicago

Returning for its third year, this multi-day celebration of stand-up brings over 20 comedians (and counting) to six iconic venues across the city—from the Chicago Theatre to the legendary Zanies, where punchlines have been landing since before you were born. The 2025 lineup includes heavy-hitters like Fortune Feimster (Nov. 8, Chicago Theatre), Pete Holmes (Nov. 6, Riviera Theatre) and an array of scene-stealers like Earthquake,  Marie Faustin and Joe Machi. 

With soundstage-sized pieces like horned sculptures emitting soap bubbles, inflated spheres bedecked in abstract squiggles and surreal faceless figures hovering in space, “EmotionAir” reimagines the humble balloon as any other artistic medium—a conduit for creativity and emotion. 

The Cubs may be hibernating for the winter, but Gallagher Way provides some excellent reasons to hang out in Wrigleyville during baseball's offseason. The Wrigley Field-adjacent space hosts a variety of seasonal activities, including photos with Santa, a winter market, carnival rides and holiday movie screenings. 

More than two million lights cover the trees, fences and structures in the Brookfield Zoo at this annual holiday event, which is now in its fourth decade. Guests can walk through a 300-foot-long tunnel featuring colored lights synchronized to music, spot larger-than-life illuminated animal sculptures, gaze up at a 41-foot-tall lit tree and warm up with concessions such as funnel cakes, pizza, spiced wine and hot cocoa. 

Work up an appetite for the afternoon feast at this beloved Thanksgiving tradition, which sends runners on a 5K or 8K course that begins in Lincoln Park. You'll usually see participants dressed up as pilgrims, poultry and superheroes thanks to the race's “costumes highly encouraged” policy, but you're welcome to stick to your regular running attire. After zipping through the course, stick around Lincoln Park for the Turkey Day Tailgate, where you can go play cornhole, enjoy hot cider and eat donuts—because there's nothing wrong with a sweet appetizer before your Thanksgiving meal.

Skate under the Chicago skyline and within eyeshot of the Chicago Christmas Tree at the McCormick Tribune Ice Rink in Millennium Park. Plus, take advantage of free skating lessons on most Saturdays and Sundays, where you can learn both beginner- and intermediate-level skills. 

The iconic German-inspired holiday market at Daley Plaza brings just over a month of Christmassy celebrations to the Loop. Browse stalls stocked with handmade gifts, German food and plenty of hot beverages to keep you warm while you wander around and soak in the festive atmosphere. Don't leave without trying spiced glühwein, a German hot wine concoction that's best enjoyed in the market's famous boot mugs.

Why settle for watching a parade weave through New York City on TV when you can see giant cartoon character balloons, marching bands and dancers on the streets of Chicago? If you happen to be in the city on Thanksgiving, you can catch the annual procession before digging into your turkey. Moving down State Street between Ida B. Wells Drive and Randolph Street, the parade finishes by 11am, which means you'll have plenty of time to get home and help with the cooking.

Situated in the heart of downtown Chicago with the city's sweeping skyline as a backdrop, the Skating Ribbon at Maggie Daley Park is a winter attraction unlike any other. Skaters can lace up and wind around a winding ice-covered path that's twice the length of a lap around a traditional rink. 

Every local thrifter worth one's salt knows that Vintage House Chicago holds some of the city's best thrift scores. The bimonthly vintage and handmade market showcases local makers at rotating venues throughout the city. Each market features a new lineup, so you can plan on finding something new every time.