The best November 2026 events in Chicago

Why settle for watching a parade weave through New York City on TV when you can see giant cartoon character balloons, marching bands and dancers on the streets of Chicago? If you happen to be in the city on Thanksgiving, you can catch the annual procession before digging into your turkey. Moving down State Street between Ida B. Wells Drive and Randolph Street, the parade finishes by 11am, which means you'll have plenty of time to get home and help with the cooking.

The Chicago Botanic Garden hosts this annual (and quick to sell out) display of festive lights, giving guests a host of shimmering reasons to visit the forest preserve during the holiday season. Set along an illuminated path, the after-dark experience features a series of installations to explore, including a 110-foot tunnel made up of 100,000 lights and a group of trees festooned with bulbs that "sing" holiday songs. 

The circus is coming to town as Ringling Bros. and Barnum & Bailey presents a reimagined version of The Greatest Show on Earth from November 6-8. The new tour won’t have any animals, but instead features musical performances blended with aerial artistry, modern comedy and never-before-seen acts on highwire, trapeze, bicycles and more. Performers include The Navas Troupe on the Double Wheel of Destiny, unicyclist Weslley Williams, and trapeze group Flying Cáceres.

What's the ultimate reward for finishing a race? If you answered "chocolate," then you should probably sign up for the Hot Chocolate Run or Walk, an annual race that ends with all types of sweet treats. Participants get a race-themed hoodie, a medal that looks like a cup of hot cocoa, and access to a post-race gathering where chocolate goodies will be served.

The Music Box Theater brings back its beloved annual Halloween tradition with five screenings of The Rocky Horror Picture Show. Each screening is paired with a shadowcast as actors perform in front of the screen during the film. It's a wonderfully weird tradition that's known to sell out.

“Rashid Johnson: A Poem for Deep Thinkers” is a major survey spanning the Chicago artist’s nearly three-decade career. Through photography, video, immersive painting and large-scale installation, the exhibition explores the fragility of the human psyche against the weight of historic forces. Centering freedom as his primary muse, Johnson draws inspiration from radical movements of the late 20th century, showcasing how individuals and communities resist established orders to carve out new paths through history.

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.

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.

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. 

Every year, the Griffin Museum of Science and Industry puts up its four-story Grand Tree and surrounds the towering pine with more than 50 trees that represent Chicago's various communities and their respective holiday celebrations. Visitors will be able to take in even more seasonal cheer at the accompanying Holidays of Light exhibit, which recognizes the traditions of Chinese New Year, Diwali, Kwanzaa, Ramadan, Hanukkah, Visakha Puja Day and St. Lucia Day. Admission to Christmas Around the World and Holidays of Light is included with a regular Museum of Science and Industry ticket.

Hosted at Stolen Saddle—one of Chicago's largest country bars—this annual Halloween-themed extravaganza features photo ops galore, plus an upstairs bar serving spooky cocktails like Freddy’s Tequila and Darcula's Blood. There’s no haunted house this go-around—but that doesn't mean Nightmare on Clark Street won't be serving up scares this Halloween season.

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.

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.

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.

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. 

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. 

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.

Every Wednesday, the Old Town School of Folk Music hosts a showcase of world music and dance. Featuring both local and touring talent, you're sure to hear something new and exciting at this long-running series. Before the show, be sure to peruse the Old Town School of Folk Music Store, where you can rent instruments, learn about lessons and peruse a wide selection of books.

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.

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.

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.

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.

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.

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.

The team behind the popular Drunk Shakespeare series puts a spirited spin on the holidays with the return of Drunk Christmas Carol. The 90-minute rendition of Charles Dickens' iconic story features a completely sober cast, minus one actor who takes five shots before performing. 

Explore a host of galleries and programming at this monthly event that showcases West Town’s dynamic arts community. On the first Friday of every month, galleries and arts-based businesses stay open until 8pm.

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.

Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. Stationed just a stone's throw away from the Adler, the Doane Observatory is also home to the largest public telescope in the area and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.

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.

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.

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.

Located inside The Den, a 1920s greystone-turned-hotel in Lakeview, the Blind Wolf Speakeasy is an intimate, approachable bar, event venue and home to a free weekly comedy show. Blind Wolf Comedy hosts a rotating roster of Chicago comics each Wednesday at 8pm, as well as open mic nights on Thursdays at 7:30pm. There's no cost to attend, but you can reserve a seat through their Instagram page.

The Whistler’s monthly lit series pops up on the second Wednesday of every month, bringing an evening of readings, workshopping and discussion to the Logan Square cocktail bar. Each show is followed by an installment of the Relax Attack Jazz Series, a free event with a constantly rotating bill.

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.

"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. 

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.

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.