The best things to do in Chicago this weekend

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.

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. 

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.

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 one blissful Sunday, the gridlock traffic and blaring car horns that typically characterize Wicker Park's stretch of Milwaukee Avenue will be replaced with cheery pedestrians and cyclists, live music, exercise classes, sidewalk sales and more—all thanks to Meet Me On Milwaukee. The pilot series of “pedestrianization” events—organized by Alderman La Spata, the Wicker Park Bucktown Chamber of Commerce and the Chicago Department of Transportation—will close Milwaukee Avenue to car and bus traffic between North/Damen and Ashland Avenues. 

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.

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. 

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.

Get your fall feels on at this free festival that begins at the tail end of September. You can snag a photo with a giant pumpkin, watch master carvers at work, enjoy live music and see all kinds of animals. The festival also includes several ticketed experiences such as carousel rides, a bounce house, harvest maze, a slide 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 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.

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.