The best things to do in Chicago this weekend

Once again, Prison City Vintage and Dibs Vintage are curating a weekend-long thrifting extravaganza—and this year's Illinois Vintage Fest is bigger than ever. Stationed at the DuPage County Fairgrounds, two entire buildings will be stocked with some of the Midwest's best thrifters and clothing slingers. Beyond new wardrobe additions, expect artisanal goods, collectibles, homewares and more.

The baseball season is still a few months aways but there will be plenty to talk about at the North Siders’ annual convention, which features panels, player meet-and-greets, autograph sessions and interactive experiences. If you're a die-hard Cubbies fan, this is just as sacred as a pilgrimage to the Friendly Confines.

In Peter Shaffer’s Amadeus, genius is not just a blessing: It’s a declaration of war. Composer Antonio Salieri sees himself as one of its principal casualties. Once the darling of the 18th-century Viennese court, he watches in mounting horror as Mozart launches an artistic takeover that endangers not just Salieri’s career but his very conception of himself. Above all, Shaffer offers a haunting portrait of two artists with irreconcilable visions of art, love and faith, but drawn again and again to the same creator: the keyboard.

Looking for an alternative to alcohol this January? Some of the city’s best bartenders and mixologists are coming together to create a selection of zero-proof drinks. Guests will get to sample all of the offerings and vote for their favorite. In addition, non-alcoholic spirit, wine, beer and seltzer brands will be on hand to provide tastings of their products as well. A portion of all ticket sales will benefit Ben's Friends, a charity supporting food and beverage professionals affected by addiction.

Elevate your morning routine with an exclusive wellness experience at The Auditorium. Held in the breathtaking Dress Circle, this unique Pilates session unfolds beneath sweeping arches and gilded architecture, offering dramatic views of the world-famed stage. Following the workout, enjoy a curated Beyond Yoga pop-up, a complimentary prosecco toast and healthy refreshments from Chicago Gold Coast Health Foods. Each ticket also includes a guided tour, providing a rare behind-the-scenes look at this historic landmark.

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. Prices vary from show to show; visit the website for the full schedule.

This family-friendly exhibition explores six habitats—Desert, Ocean, Rainforest, Sky, Woods and City—through the eyes of modernist artist Charley Harper. Designed to foster appreciation for biodiversity and interdependence, the exhibit includes interactive games, a DIY soundscape station and multisensory interpretations of Harper’s beloved work.

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.

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. 

Just when you thought the state's largest mall couldn't surprise you anymore, Woodfield Mall announces WONDRA, a sprawling new immersive experience. Inside, you’ll wander through enchanted meadows that respond to the sound of your voice, stumble across bioluminescent landscapes and drift into crystal caves and celestial gardens that blur the line between digital spectacle and raw wonder. 

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.

Most people call January “the first month of the year” or “four weeks of taking my resolutions seriously,” but Chicago blues fans know that it's actually “Buddy Guy month.” Throughout the month, the legendary bluesman picks up his polka-dot guitar and takes the stage during a residency at the South Loop blues clubs that bears his name. Guy performs every Thursday, Friday, Saturday and Sunday night, with a different supporting act joining him each evening. This year, you'll see Guy paired with folks like Bobby Rush, Katie Kadan and Michael Damani. Tickets to Guy's January residency aren't exactly cheap, but witnessing a bonafide blues icon perform in his hometown is the kind of experience that's worth the dough.

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.

“Mutuality” a group exhibition of new works created during the 11th year of the Hyde Park Art Center’s biennial Center Program, a professional development program designed to elevate emerging and mid-career artists. The exhibition defines mutuality as demonstrating mutual care and interest, encouraging artists to consider how their intentions, works and practice impact the world. Artworks in “Mutuality” represent over 20 artists practicing a multitude of disciplines, from painting and drawing to fiber and printmaking to performance and sound.

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.

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. 

Immerse yourself in a picture-perfect whimsical décor, sparkling lights and breathtaking Chicago skyline views from the 22nd floor and indulge in a delightful selection of holiday-themed cocktails, including steaming spiced mulled wine and chilled festive drinks. 

“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. 

Andrew Lloyd Webber's bombastic megamusical haunts the Cadillac Palace for a spectacular eight-week run. The age-old tale of love, loss and revenge unfolds against the Baroque interior of the Cadillac Palace Theatre—transporting you straight to late 19th-century Paris. 

Andrew Lloyd Webber's bombastic megamusical haunts the Cadillac Palace for a spectacular eight-week run. The age-old tale of love, loss and revenge unfolds against the Baroque interior of the Cadillac Palace Theatre—transporting you straight to late 19th-century Paris. 

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.

Find your flow with the whole family in the cozy confines of the Peggy Notebaert Nature Museum at a Brain to Belly Kids Yoga session! This creative class flows through several fun poses, each one complementing the month's children's story. Children (ages two to eight) and their grown-ups will enjoy moving, breathing and connecting together while bringing the story's plot to life. Bonus: Your ticket includes full access to all museum exhibits, so stick around after class!

The DuSable Black History Museum and Education Center's newest exhibition, “Paris in Black” charts the journeys of Black artists, performers and intellectuals who found a safe haven and creative incubator in 20th century Paris. Experience the City of Lights through the eyes of visionaries like Langston Hughes, James Baldwin and Henry Ossawa Tanner, who lived and created in defiance of American racism. The exhibition houses over 100 objects, including magnificent paintings, historic photographs and multimedia elements—all telling the story of Black resilience and artistry.

Known for his groundbreaking homes spanning across the United States and rejection of minimalist conventions, Bruce Goff—whose lifelong mentor was Frank Lloyd Wright—is one of the modern world's most celebrated architects. To celebrate his legacy, The Art Institute of Chicago will be hosting the first major exhibition of Goff’s work in 30 years. The show will feature more than 200 works celebrating every phase of Goff's creative practice, from elaborate architectural drawings and models to a selection of Goff's lesser-known artistic output in abstract painting.

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.

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.

You’ve probably seen a Shakespeare play before, but never like this. Five professional actors come together for each performance of Drunk Shakespeare. The twist? One of them has had five shots before the show and is trying to stay on track while the other four actors do their best to hold the performance together.

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.

Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 North Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levels—you just need to bring your own mat and arrived properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.

The Godfrey’s rooftop becomes a winter wonderland when the temperatures plunge, featuring clear heated igloos decorated with festive lights that can be booked for groups of up to 10 people indulging in bottle service. Even if you’re not going all out, you can hang out at a booth under the retractable roof or gather around an outdoor fire pit for s’mores and a hot cocktail.

Produced by World of Wonder—the company behind Drag Race and the global DragCon conventions—the attraction casts visitors as the main character inside some of the show’s most iconic spaces. You can strut the Main Stage, snap a selfie in the Werk Room, film a confessional and flip through racks of costumes pulled straight from the runway. Roll up with your squirrel friends and you’ll have a day that’s pure eleganza.

For more than 30 years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. The company's signature show is more unpredictable than ever these days, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.

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.

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.