The best December 2025 events in Chicago

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. Note that you'll need to make a free online reservation for both regular skating and lessons, and if it seems too warm to skate, call ahead—this rink is open through early February 2026, weather permitting.

Every year, Millennium Park is adorned with an epic Christmas tree that remains on display until the beginning of the new year. The larger-than-life attraction is festooned with twinkling lights and crowned with an illuminated star. Spectators can check out the festive tree near Washington Street and Michigan Avenue through early January. Want to see the tree light up for the first time this season? The annual Christmas Tree Lighting Ceremony returns this year on Friday, November 21.

Happy’s is back for its farewell season, and they're closing out a holly, jolly run in full holiday spirit. Situated on the ground floor of the Chicago Athletic Association, Happy's transforms the hotel's Tank space into a holly, jolly wood-paneled dive bar serving cocktails and bar bites. Admission is free, and the pop-up is just a short walk from the Millennium Park ice skating rink.

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. Reservations for the popular ice rink should be made in advance, as they tend to fill up quickly.

Admission to the Skating Ribbon is free Monday through Thursday and for 11am sessions Friday through Sunday (and $5 for other time slots Friday through Sunday, as well as holidays) if you bring your own skates. No skates? Entry is $17–23 if you need to rent a pair. The Ribbon stays open through March (weather permitting) and even offers hours on Thanksgiving Day, Christmas Eve, Christmas Day, New Year's Eve and New Year's Day.

Don't forget to hit the ice during your next visit to Winterland at Gallagher Way! Until February 15, 2026, visitors can rent ice skates for $16 or bring their own, ride ice bumper cars and more. Check out the Gallagher Way website to stay updated on skate nights, skating lessons and curling matches—all beginning January 2026.

See Christmas lights while staying warm at this pandemic-era innovation that allows visitors to drive through a gleaming tunnel of more than one million LED lights synchronized with holiday music. Plus, the show takes place in Bridgeport at Rate Field, home of the Chicago White Sox.

Bring a thermos of hot chocolate and a cozy blanket to accompany your ride through Willow Hill Lights, a drive-through holiday light experience in suburban Northbrook. Located at Willow Hill Golf Course, the 2.5-mile display of glittering lights features holiday favorites like Rudolph and Frosty the Snowman—not to mention a 30-foot-tall Christmas tree. Proceeds from the show benefit Misericordia, a not-for-profit that supports more than 600 children and adults with intellectual and developmental disabilities.

Slide past an indoor skydiving center and Fogo de Chão on the Chicago Wolves Ice Rink at Rosemont's Parkway Bank Park, where you can hit the ice on most days through the end of January. Check the official website for hours. Admission is free, and skate rentals are $8 per pair.