The best January 2026 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.

Open wide! Chicago Restaurant Week is back for its 19th year. More than 470 Chicagoland eateries will offer specially curated prix fixe menus for brunch ($30), lunch ($30) or dinner ($45/$60) between January 24 and February are 9. With more than two weeks to chow down, there's plenty of time to make a few reservations and check out some of the best restaurants in Chicago while saving some coin.

Prepare for a magical adventure: Disney on Ice is coming to United Center and Allstate Arena for its latest show, Jump In! The ice-skating spectacle promises awe-inspiring visuals, thrilling stunts and mesmerizing choreography featuring over 50 of your favorite Disney characters. Along with aerial acrobatics and interactive elements, Disney on Ice will also welcome a few new characters to the crew: Anxiety, Joy, Sadness, Disgust, Anger and Fear from Inside Out 2 and multiple new characters from Moana 2 will be lacing up their skates.

Every two years, Chicago becomes a global hub of architecture and design during the Chicago Architecture Biennial. This edition’s theme is SHIFT: Architecture in Times of Radical Change, bringing together over 100 projects by architects, artists and designers from 30 countries—each piece engaging with the cultural, social and environmental fluxes transforming our world. Not sure where to start? Check out our first-timer's guide to the exhibition. 

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.

Pinkmas at the Museum of Ice Cream is more than your run-of-the-mill holiday outing—it's a dazzling, immersive holiday experience. Visitors can share their wildest dreams with a Wishing Tree, walk through a life-size snowglobe, and feast on festive treats and ice cream creations, all while taking advantage of countless photo opportunities.

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 newly renovated Intuit Art Museum is the perfect place to visit the exhibition, “Catalyst: Im/migration and Self-Taught Art in Chicago.” This exhibition is part of a citywide initiative highlighting Chicago's artistic heritage and creative communities. “Catalyst” focuses on the impact of immigration and migrant experiences within the self-taught artist community. The featured works investigate the inciting incidents for artists' displacement and subsequent settling in Chicago, offering a unique perspective on artistic practice as a personal narrative.

While all of the other music festivals are in hibernation, Tomorrow Never Knows has been bringing up-and-coming artists to venues all over the city for the past 20(!) years. Organized by the folks at Schubas and Lincoln Hall, the lineup usually sports an abundance of rising acts who perform at the organizing venues as well as Bridgeport's Ramova Theatre. This year, you'll be able to catch a variety of bands, including dream-folk luminary Cassandra Jenkins, Chicago instrumental two-piece Mute Duo, avant-pop sensation Perfume Genius and more.