The best things to do in Chicago today

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.

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.

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.

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. Every corner is crafted to ignite curiosity and inspire a sense of awe we, whether you’re a kid seeing it all for the first time or an adult who forgot what it feels like to play.

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.

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 local thrifter worth one's salt knows that Vintage House Chicago is a treasure trove holding some of the city's best secondhand scores. The bimonthly vintage and handmade market showcases local makers and curators at rotating venues throughout the city. Each market features a new lineup, so you can plan on finding something new every time.

Drag Race: The Experience has sashayed into Chicago for a one-month stint. But does it bring the requisite charisma, uniqueness, nerve and talent? Well… yes and no. 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. There’s never-before-seen footage playing across a glowing wall of retro TV screens, an abundance of photo ops and QR-guided prompts that politely boss you from room to room. Guests are given a unique QR code to use with the scanner in each room, enabling them to collect photos throughout their visit. The layout isn’t especially intuitive, but if you approach it as one giant, glittering selfie machine, the whole thing snaps into relative focus. There are costumes, clips and even a full Snatch Game set, ready for you and your friends to butcher celebrity impressions with enthusiasm if not accuracy. The experience ends in an atrium where you can retrieve your photos, sip a drink at the Gold Bar, shop exclusive merch (yes, including a “shantay” fan) and attempt a Best Friend Race-style scavenger hunt. During its run, Drag Race: The Experience will host screenings and premiere parties across the Drag Race universe. The space is also rentable for private events, which may be when...

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 “the creature”—his term for the rising musical prodigy Wolfgang Amadeus Mozart—launches an artistic takeover that endangers not just Salieri’s career but his very conception of himself. The scaffolding of his principles collapses beneath his suspicion that God has chosen someone else above him, and his devotion rots into destruction. Amadeus | Photograph: Courtesy Michael Brosilow Salieri never leaves the stage. Recounting his venomous rivalry from the safety of his deathbed, he is both Amadeus’s antagonist and its narrator, and his voice is the lens that refracts the entire story. Once he had offered his life in monastic devotion to music and to God; now he confesses how swiftly he turned away from both when Mozart revealed what true genius sounds like. In a lesser actor’s hands the role might wear thin, but Ian Barford, seasoned in Steppenwolf cynics since 2017’s Linda Vista, is magnetic. Salieri insists on being the omniscient puppeteer behind Mozart’s downfall, yet the audience can’t quite believe him. His envy is so vast it becomes its own orbiting body, circling a sun named Mozart. That sun is played by David Darrow, whose Mozart radiates an irresistible, maddening charm. Darrow leans into the character’s impish, sophomoric...

“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.

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.

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.

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.

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. LondonHouse Chicago's rooftop also offers cozy heated igloos, which can be booked by contacting rsvp@londonhouse.com; reservations require a $600 food and drink minimum.

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.

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.

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.

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. 

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.

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.

“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.

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.

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.

Pegasus Theatre Chicago presents its 38th annual slate of competition-winning one-acts by Chicago high school students, staged and performed by professional directors and actors. This year's featured plays are Love & Gyros by Lily Zhang, Family Fishing Trip by Lydia Vodopic and Superheroes Anonymous by Carolina Boss.

If dozens of vendors aren't enough of a draw for you to come to the lively Sunday market at this West Town neighborhood’s namesake park, maybe the weekly complimentary market programming—which includes free yoga, meditation and storytime for kids—will be. The market is also committed to sustainability, with plastic-free vendors and composting.

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.

Watch the planes fly out of Midway while you glide across the ice on the rink at Wentworth Park. If you're looking for something to do after your fingers are frozen, consider heading south for a beer at the 5 Rabbits Cerveceria. (See the park's website for ice rink hours.) Skate rentals are $6.

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.

Wanna relive the thrill of punishing a captive audience like you did during grade school show-and-tell? Then Show & Tell for Grownups is the place for you! Once a month, comedians, storytellers and everyday passionate folks gather to share their quirky, heartfelt or downright fascinating interests. Each presenter gets five minutes on the clock to wax philosophical about their obsession, then it’s the audience’s turn with a quick Q&A. Think of it like falling down a Reddit rabbit hole—only live, and way more fun. Feeling especially brave? Sign up for your five-minute show-and-tell slot here.