The best things to do in Chicago today

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. 

The inaugural Chicago Art Fair brings top galleries from across the globe to THE MART this fall. The four-day event, ideal for collectors, designers, buyers and art enthusiasts alike, showcases contemporary and modern fine art paintings, sculptures, photography, mixed media and more in a massive space at the downtown design destination. Organizers announced that next year, Chicago Art Fair will also include the return of SOFA (Sculpture Objects Functional Art) Fair, which has been on pause since 2022.

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

Returning to a two-acre plot of land just west of Goose Island, Jack's Pumpkin Pop-Up saves you a trip to the suburbs by bringing a huge corn maze, thousands of pumpkins, axe throwing, carnival games, food trucks, twinkling orange light displays and more fall fun to the city. A general admission ticket gets you access to the pop-up, but you can also opt for add-ons that let you take home a pumpkin, grab a drink at one of bars or go axe throwing.  When is Jack's Pumpkin Pop-Up? The pop-up opens September 19 and runs through November 1. How do I get tickets to Jack's Pumpkin Pop-Up? Timed-entry tickets can be purchased via Jack's website. Prices vary based on time and ticket type.

Get in the holiday spirit at this annual ghoulish makeover of the Chicago Botanic Garden. The event brings together more than 1,000 real pumpkins—some weighing up to 150 pounds—which are LED-lit creations and staged along the garden's pathway, where other entertaining characters and activations await visitors. This year, a new 20-foot inflatable sculpture called "Monarch Skull" by artist Alyse Gamson joins the Garden's elaborate Halloween takeover. Seasonal snacks and drinks are available for purchase, in case all that wandering makes you hungry. 

Celebrating Chicago culture through couture, Chicago Fashion Week brings runway shows, markets, educational programs and more—many of which are free to attend—throughout the city. The third edition of the celebration of Chicago's fashion scene features programming like  panel discussions on styling and beauty standards, runway debuts, pop-up shopping events, and networking mixers. Check out the full schedule on CFW's website.

Spooky season will get a bit boozier this year thanks to this horror-themed cocktail pop-up at the Albion Manor, where Halloween lovers can sip expertly mixed cocktails amid metal music and goth decor. Drinks are imbued with playful touches and include choices like Abyssa’s Obsession made with pumpkin-infused rums, and the tequila-based Bone Temple. Want to recreate the creepy vibe at home? Several of the drinks are served in Halloween glassware that’s available for purchase onsite.  

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. Having made its U.S. debut at the Field Museum in May, the immersive 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 activations throughout.

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.

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.

If three hours in the theater wasn't enough Odyssey for you, then you're in luck. The National Hellenic Museum is celebrating the most iconic story of all time with a lineup of programming centered around Homer's epic, including the art exhibition The Odyssey Reimagined. Featuring works by 17 contemporary artists, the exhibit explores the current-day connections to the nearly 3,000-year-old story through paintings, photography, textiles, sound and more. 

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.

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.

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.

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.

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.

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.

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.

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.

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. What separates the Chicago Architecture Center River Cruise from similar tours are the knowledgeable Chicago Architecture Center docents that lead each excursion. You'll be able to chat with experts who know the nitty-gritty details of Chicago architecture and are eager to help you learn more about the structures surrounding you—something that makes this attraction appealing to tourists and longtime residents. All tours depart from the First Lady dock on the Chicago Riverwalk, located just down the stairs from the northeast corner of Michigan Avenue and Wacker Drive. If you want to continue learning about Chicago's buildings after your tour, you can add a Chicago Architecture Center ticket for just $5—and it's good for seven days after you board the boat.

Round up your family for a wild, multi-week Halloween festival at Brookfield Zoo. Decorate a pumpkin, take a spin on the decked-out carousel or pose for photos amongst giant inflatables and wooden cut-outs of Halloween characters. The not-too-spooky event also treats some of the zoo's animals—including gorillas, goats and lemurs—to pumpkins that they can play with, nibble on and smash. 

"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. 

This touring exhibition honoring one of the country's most significant sculptors of the 19th century stops at the Driehaus Museum. Known for major works like the Bethesda Fountain in New York City's Central Park, Stebbins' marble and bronze works are showcased in this career-spanning exhibition of sculptures, paintings, archival materials and more.

Bucktown entertainment destination WhirlyBall is introducing a new arcade, and they're offering a weekend of free games to celebrate. For three days, guests can enjoy free gameplay in the new arcade on all non-prize games. 

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.

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.

Need motivation to exercise? Head to the Obama Presidential Center on Thursday mornings for its weekly walk/run. This free event invites older adults to join in a walk or light run, starting in Jackson Park Field next to Home Court and through the manicured campus grounds. Participants are first led through a warm-up and are encouraged to take breaks at any time during the walk/run. There's no cost to sign up, but make sure to RSVP online before heading over.

Explore the historic Old Joliet Prison under the cover of the night this spooky season. In the Flashlight Tour, guests will wander through the facility with just a flashlight as they learn about the prison's operations and dark history.