The best November 2025 events in Chicago

Returning to a two-acre plot of land just west of Goose Island, Jack's Pumpkin Pop-Up saves you a trip to the suburbs by bringing a huge corn maze, more than 10,000 pumpkins, axe throwing, carnival games, food trucks, twinkling orange light displays and more fall fun to the city. A general admission ticket nets you access to the pop-up, but you can also opt for add-ons that let you take home a pumpkin, grab a drink at one of bars or go axe throwing. 

Hosted at Stolen Saddle—one of Chicago's newest and largest country bars—this annual Halloween-themed extravaganza features a multi-level haunted house as well an upstairs bar serving spooky cocktails. There will also be photo ops galore and plenty of other spooky surprises.

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.

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. 

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.

More than 115 emerging artists will be selling their work at Saatchi Art's touring art fair, which takes place this year at Artifact Events. Prices for art start at around $100, making this the perfect opportunity for burgeoning collectors to start their very own gallery wall without spending an arm and a leg. 

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.

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.

The Chicago Botanic Garden hosts this annual (and quick to sell out) display of festive lights, giving guests a host of shimmering reasons to visit the forest preserve during the holiday season. Set along an illuminated path, the after-dark experience features a series of installations to explore, including a 110-foot tunnel made up of 100,000 lights and a group of trees festooned in bulbs that “sing” holiday songs.