The best February 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—this rink is open through early February 2026, weather permitting.

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.

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. Stay up-to-date by visiting the Chicago Architecture Biennial website.

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. 

Located on the terrace of The Peninsula Chicago, the 2,100-square-foot Sky Rink offers ice skating in the shadows of the city's tallest buildings, all while overlooking Michigan Avenue. Show off your skills in a winter wonderland featuring snowflake lighting and festive music, and when you need to warm up, grab a hot drink and snack at the Chalet.

Visiting “The Land of Oz: Beyond the Page” at the Gold Coast’s Driehaus Museum feels a bit like opening a very elegant jewelry box: beautifully crafted, lovingly arranged and also...surprisingly compact. Tucked away into two rooms on the museum’s top floor, the film-inspired exhibit offers a curated peek behind the yellow brick road—costumes, concept art, early editions of L. Frank Baum’s original book and just enough memorabilia to spark a pleasant jolt of nostalgia. The exhibit's highlights include a replica of Dorothy’s slippers—one of only 20 editions worldwide—and a collection of “movie edition” Wizard of Oz books adjusted to better match the silver-screen adaptation. In the end, the Driehaus Museum’s Wizard of Oz exhibit doesn’t attempt to sweep you away in a tornado of spectacle so much as hand you a small, neatly labeled basket of curiosities. Its strength lies in details—like early drafts of the film’s script and a replica of the Cowardly Lion’s courage medal, which was a departure from the book’s bottle of courage the character drank. It’s these little factoids that make the exhibit worth a visit. While the exhibition may leave devoted Oz scholars wanting more, it offers casual visitors a gentle, concentrated dose of nostalgia within the museum’s ornate surroundings. You may not walk out feeling as though you’ve traveled all the way to the Emerald City, but you will have enjoyed a tidy, thoughtfully assembled layover somewhere between fantasy and reality.

Until February 2026, the University of Chicago's Smart Museum of Art hosts “Unto Thee,” Theaster Gates's first solo museum exhibition in his hometown of Chicago. Known for his installations merging sculpture, performance and social practice, Gates has become a driving force in the contemporary art world and beyond. “Unto Thee” embodies the relationships Gates has fostered throughout Chicago, underpinning his belief that art has the capacity to connect and transform communities.

“Music of the Mind” is a retrospective that celebrates key moments of Ono’s career, showcasing art driven by ideas and expressed in poetic, humorous and profound ways. Tracing Ono’s career back to the 1950s, “Music of the Mind” presents over 200 works across a variety of media including performance footage, music and sound recordings, scores, film, photography, installation and archival materials. The exhibition also features participatory works—a key component of Ono’s creative practice—where visitors are encouraged to interact with instruction-based artworks.

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.

“Living with Modernism: Kelli Connell” presents two series of photographic works by the Chicago artist. The exhibition's first body of work, “Pictures for Charis” finds Connell responding to iconic Edward Weston photographs through a queer, feminist lens. The second major work, “Double Life,” spurs a dialogue with the Mies van der Rohe-designed McCormick House while charting the evolution of nature, identity and relationships. This exhibition marks the largest presentation of Connell’s work in Chicagoland, placing queerness, power structures and shifting ecologies to the forefront.