The best things to do in Chicago this weekend

Middle Brow is adding another street fest to the calendar this year with its inaugural Armitage County Fair. The two-day fest features live music across two stages, comedy sets, a petting zoo and county fair-style competitions like greased-watermelon races and giardiniera-eating contests. The food and beverage lineup will exclusively feature local brands like Lonesome Rose, Pretty Cool Ice Cream, Gretel, Marz and Giant.

Whether you're looking to brush up on your Korean, Japanese or Mandarin Chinese, or are just looking for something out-of-the-box to do, check out the language and culture exchange Sip and Speak. Taking place at the Gangnam Market Food Hall, the free event lets language learners of all levels practice their skills over famous Asian games like Gonggi, Mahjong and Go. Admission is free (though a $10 donation is suggested), but attendees are encouraged to reserve a ticket in advance.

Get ready to hunt for some new (and old) treasures! The beloved Randolph Street Market Festival is back with two days of curated, European-style vintage and antique shopping. Browse wares from hundreds of vendors, or grab a cocktail and bite to eat from local restaurants while tapping your toes to live music. 

They say that there's nothing more American than apple pie, but we're of the opinion that the most patriotic food of all is the chicken wing. Soaked in a variety of different sauces (from classic buffalo to Asian ginger, spicy garlic and honey chili), it's a versatile dish that has become a national staple. WingOut Chicago celebrates the venerable chicken wing, inviting cooks from Jake Melnick's, Smoke Daddy and more to put their spin on the dish. General admission includes entry and access to live entertainment, with the option to purchase à la carte wings and beverages. Opt for VIP tickets for early entry, all-you-can-eat wings and a drink package.

A new street fest is coming to town with the debut of Clark Street Live in Wrigleyville between Addison Street and Newport Avenue. The two-day fest features food and drinks from local spots, plus live music across two stages. This year's lineup includes country artist Matt Stilwell and tribute band Radio Gaga. 

Taking place in and around Lakeview’s St. Alphonsus Church, this autumn event features the requisite selection of suds, brats, pretzels and two stages of Bavarian music along with sets from local cover bands like Dancing Queen: An ABBA Salute. Activities include a stein-holding contest, polka dancing and a “Kinderfest” for the kiddos on Sunday. 

The Chicago Cultural Center is free and open to the public throughout the majority of the year, but if you need an excuse to check out all it has to offer, an Open House should do the trick. This year, the event will feature live music, gallery exhibitions, shopping and more. For a full schedule of activities and to RSVP, visit the official website.

Set sail with Chicago Line Cruises for an evening of jazz on the river. On the last Sunday of each month through September, the cruise line is partnering with the Jazz Institute of Chicago for 90-minute cruises featuring live performances, an on-board bar, open-air decks and a prime view of the sunset.

Find the perfect vintage piece for your collection at this Andersonville market, where you can shop antiques, home decor, jewelry, clothing and other trinkets from over 30 vendors on six different dates throughout the summer. Participating businesses include Antiqueandmod, J-Bird Clay, Scal's Vintage, The Paper Archive and many more.

Lincoln Park exhibition space Wrightwood 659 presents an engaging show that features the works of three trailblazing women: Yayoi Kusama, Niki de Saint Phalle and Mary Bauermeister. Inner Worlds showcases large-scale works, mixed-media works, sculptures and more by the artists, who are acclaimed for their approaches to perception and embodiment. Highlights of the exhibit are two of the late Kusama's Infinity Mirror Rooms.

Chicago's largest Oktoberfest celebration is returning to the heart of Fulton Market. Located just behind Restaurant Row at 171 N. Peoria St., this lively six-week German fest is pouring Hofbräu München beer imported directly from Germany. Guests can also expect Bavarian pretzels, brats, live German music, carnival games and more. 

From model to battlefield correspondent—and with many other titles in between—Lee Miller was a complex figure, and this year, the Art Institute of Chicago is showcasing works from her career in an expansive exhibit titled Lee Miller: Fearless. The first comprehensive survey of Miller's photographs in more than 25 years, Lee Miller: Fearless will feature nearly 150 works and will explore her life and approach to creativity, both behind and in front of the camera.

Celebrate Oktoberfest over the course of three weekends at The Northman Beer & Cider Garden, which is bringing a host of festivities to its Riverwalk digs this September and early October. Expect giant pretzels and German sausages, beer steins and polka music, and scenic waterfront views with a European vibe.

Explore music from around the globe during this annual festival, now in its 24th year, which brings a wide array of performers to venues across the city for free musical performances. Experience sounds and subgenres from regions like Brazil, South Korea, Senegal and more. For a full list of performances, visit the festival's website. 

Explore Chicago's eerie past as you snake down the river aboard the First Lady Creepy Cruise. The 90-minute tour combines architectural history with stories of the city's shady past, from mob legends to ghost sightings, for a spooky evening on the water.

Looking for a great way to start your weekend? Lululemon ambassadors and local run leaders host a free weekly run club every Saturday morning. Runs start at the brand's Rush Street store in the Gold Coast, before heading down the Lakefront Trail and back to the store for post-run snacks. The run route is 3 miles, but multiple distances and durations are offered as well. Dogs, strollers and runners of all experience levels are welcome—just be sure to sign up in advance.

Sportsman's Club's Sunday BBQ series is back for another glorious year, bringing local restaurants to the bar's patio to cook a meal that's usually paired with a beverage. For the uninitiated, the takeovers are first-come, first-served, with the featured chef holding court over the bar's grill and menu. This year's lineup includes Bar Bambi, Pizz'amici, Milli by Metric, Kimski, Mister Tiger, Diego and more.

A Gen Z version of Grease takes the stage at the Apollo Theater this season. Vape! The Grease Parody is an Off-Broadway spoof of the iconic 1978 musical, complete with playful takes on the original storylines, modern references and, yes, vapes instead of cigarettes.

Chicago-based designer Confidence Apparel is hosting a fashion show at Navy Pier to raise awareness for Suicide Awareness Month. With a theme of Hope in Motion, the evening will be emceed by Emmy Award-winning journalist Jasmine Minor and will feature a runway presentation, food and drinks, interactive activations and live art.

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.

Explore notable Impressionist Mary Cassatt's works in the first exhibit in more than 25 years dedicated solely to the American artist at the Art Institute. Known for her works depicting mothers with children and intimate caretaking scenes, Cassatt was the only American to join the French Impressionists. After Impressionism showcases paintings, pastels and prints from the time in her career when she began to take her art in a new direction.

The masterminds behind the irreverent long-running comedy show Drunk Shakespeare are unleashing their latest monster mash-up, Drunk Dracula, on the city during the month of October. The premise is simple, but no less hilarious: Dracula gets drunk, unsuspecting citizens fight for survival and Bram Stoker’s vampire classic gets a boozy makeover that’s equal parts unhinged and fun.

This exhibition poses a devastatingly powerful question: What if Emmett Till had not been brutally lynched in Mississippi in 1955? Through photography, the exhibition imagines an alternate history in which Till lived—moving from images inspired by the last meal his mother packed before his trip south to meditations on the life he might have experienced, from the rise of the Chicago Bulls to the ongoing fight for civil rights.

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.

Ready to explore Chicago's amazing architecture while floating on the river? The Chicago Architecture Center River Cruise takes place aboard a First Lady boat, transporting guests on a 90-minute tour that traverses three branches of the Chicago River and explores the stories behind more than 50 buildings that make up the city's iconic skyline.

Whether you’re parenting a pint-sized Pokémon devotee or a nostalgic millennial still clinging to a holographic Charizard card for its “possible resale value” (guilty), the Pokémon Fossil Museum is designed to surprise and delight. Making its U.S. debut at the Field Museum in spring 2026, the international exhibition invites visitors to compare Fossil Pokémon like Tyrantrum and Archeops with real-world fossils—including SUE the T. rex. Expect Pokémon models, real fossil excavation tools and immersive soundscapes throughout.

Whether it's on a minibus or on foot, this tour takes you to the locations frequented by some of Chicago's most notorious gangsters and the places that have been haunted by their ghosts. With four tours offered daily, there's always an opportunity to take a step back in time to learn about figures like Al Capone and Chicago's haunted history.

Intuit Art Museum joins the national Handwork 2026 celebration with an exhibition investigating Henry Darger’s relationship to traditional American paper crafts. Drawing on research by art historian Dr. Mary Trent, the exhibition demonstrates how Darger adapted common practices—such as making paper dolls and scrapbooks—into a complex, mixed-media narrative style. By showcasing Darger’s source materials alongside his final works, the exhibition highlights how he reclaimed these institutionalized hobbies to express the interior lives and struggles of the marginalized.

As the Driehaus Museum’s first artist-in-residence, Brendan Fernandes will transform the Murphy Auditorium into a dynamic site for sculpture, movement and sound. Inspired by the Judson Dance Theater, Fernandes’ Scores for the Murphy Auditorium will unfold as an episodic residency throughout 2026, with performances and public programs announced over time.

Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. Running for 30 minutes on Thursdays through Saturdays, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

"Flyway City: Architecture for a Flourishing Ecosystem," designed by Studio Gang and led by world-renowned architect Jeanne Gang, explores solutions to prevent the estimated one billion annual bird-glass collisions in the U.S. Through a variety of architectural models, interactive media and local artifacts, the exhibition demonstrates how urban design can coexist harmoniously with nature. 

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 arrive 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.

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.

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 every time you show up to see it.

This immersive exhibition recreates the Secret Annex where Anne Frank, her family and four others hid during the Nazi occupation of the Netherlands. Chicago is only the second U.S. city—and the first in the Midwest—to host the experience, which includes rarely seen artifacts from Frank’s life. Visitors can walk through the reconstructed hiding place while learning about Anne’s childhood, the rise of Nazi Germany and the Frank family’s years in Amsterdam. The exhibition offers a powerful look at the risks, courage and daily realities of those who lived in hiding. Admission is free on Friday, June 12 in honor of what would have been Anne's 97th birthday. Guests can also enjoy the exhibit for free with the purchase of a general admission ticket for the rest of the weekend.

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.