The best things to do in Chicago this weekend

Toast the season and spoil your pup at Barktoberfest, hosted by Sheraton Grand Chicago Riverwalk. A host of local pet businesses will be selling their wares and offering interactive, dog-focused experiences. After you’re done shopping, refuel at Chicago Burger Company with its special pup menu featuring options like a Barkuterie Board, Bark Burger, Cookie Treats and the ever-popular Pup Cup.

For one blissful weekend, Fulton Street transforms into an open-air gallery and music venue. Shop more than four blocks of art available for purchase at this family-friendly festival, where you'll also find two days of live music and no shortage of solid dining options nearby.

Fall is about more than crisp leaves and pumpkin spice—and Island Party Hut is here to prove it. The Riverwalk tiki bar’s fall fest returns with seasonal cocktails, river hayrides, a pumpkin patch and more. With live music, photo ops and a drink included in your ticket, it’s a celebration guaranteed to get you in the autumn spirit.

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? Lucky for you, we've made a first-timer’s guide highlighting some of the exhibition's best events.

Get ready, punk rockers! Riot Fest is returning to Douglass Park with a laundry list of rock, punk, metal and emo artists. The festival will also host a carnival, wedding chapel, Riot Fest Museum and more. This year's headliners include Blink-182, Weezer, Jack White and Green Day.

Labubu mania sweeps through Gangnam Market for one wild weekend. Visitors can browse a wide range of Labubus—not to mention clothing and accessories for said Labubus—available for purchase. If you're all stocked up on the plush monsters, swing by for a meet-and-greet with costumed Labubu characters or get your Labubu tattooed by viral L.A. tattoo artist Hunter Choa.

Designed as a choose-your-own-adventure experience, Move at the Shed is your chance to curate your own day of—what else?—movement. You can stretch out with a yoga session, break a sweat at dance cardio or kick back with live music from Jamila Woods. A class pass fetches you access to a whole gamut of activities, like community walks, special lounge areas and photo ops.

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, more than 10,000 pumpkins, axe throwing, carnival games, food trucks, twinkling orange light displays and more fall fun to the city. A general admission ticket nets 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. 

For 39 years and counting, the National Museum of Mexican Art has celebrated one of Mexico’s most extraordinary traditions with a multimedia exhibition. This year, “Día de Muertos: A Celebration of Remembrance” is dedicated to the Texans and New Mexicans who tragically lost their lives in 2025's flash floods. 

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.

Break out those cowboy boots and daisy dukes, because Wrigleyville Country Fest is taking the North Side by storm! For one day only, Wrigleyville will transform into Nashville's Music Row, with live music and barbecue abound. Ticket includes a whiskey shot, access to a brunch buffet and, of course, a whole day's worth of live music.

One of Chicago's most popular farmer's markets, Green City Market welcomes vendors selling regional produce to the south end of Lincoln Park (between Clark Street and Stockton Drive) on Wednesdays and Saturdays. Amid the rows of vendors, you’ll find farm-fresh eggs from Michigan, cheese from Wisconsin and scrumptious pies baked by Chicago’s own Hoosier Mama Pie Co.

Hokus Pokus Live! conjures up a wild and wicked theatrical experience starring nationally renowned drag queens Ginger Minj, Jujubee and Sapphira Cristál as the legendary Sisters. Landon Cider—winner of The Boulet Brothers' Dragula season three and the “World's Next Drag Supermonster”—stars as Billy. With big laughs, powerhouse vocals and a dash of magic, this live spectacle brings the cult classic to the stage like never before.

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 N 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.

Local Afro-contemporary dance company Red Clay Dance Company offers a creative response to the 2024 exhibition Freedom Square: The Black Girlhood Altar through dance and storytelling, honoring this living altar to missing and murdered Black girls and women. Featuring an award-winning ensemble of dancers and new music by Jamila Woods, this immersive, evening-length choreographic work serves as a sanctuary for the stories of the women and girls featured on the altar—blending dance, song, digital media and built environment to foster a resonant experience. 

With its latest exhibition, the Chicago Botanic Garden showcases the patterns and prints that adorn the natural world. Through meticulously planted gardens and nature-inspired art installations, Patterned by Nature highlights the intersection between graphic design and horticulture. Exhibition highlights include colossal embroidered flowers by Raquel Rodrigo, a collection of upcycled fashion sourced from garden materials by Columbia College Chicago’s School of Fashion and a paisley patterned succulent garden. 

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 Thursdays through Saturdays beginning at 7:30pm, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

As if you needed an excuse to spend golden hour at Time Out Market's rooftop bar—we're hosting a very special happy hour until the cold snap arrives. Sip on vibrant spritz drink specials crafted for summer lounging, complete with a live DJ spinning feel-good vibes all evening long. Whether you're here to dance, chill or just toast to the moment, this is your chance to savor the season.

You probably know young Frenchwoman Amélie’s story from the silver screen, and now you can see it in Chicago’s intimate Chopin Theater. Transport yourself to the streets of Paris with this musical that closely follows the film’s plot—Amélie seeking connection and joy through her wondrous imagination. The musical will unfold throughout the Chopin Downstairs Studio, transforming the lobby, bar, and café into set pieces.

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.