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.

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.

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.

Experimental Sound Studio's longtime partnership with the Chicago Park District and Lincoln Park Conservatory continues with “Semblance of Fern,” a new sound installation by composer Sarah Belle Reid. The immersive installation explores the formal connections between mathematical models and nature in the contemplative confines of the conservatory's Fern Room. After getting your fill of tropical palms and vibrant flowers, mosey over to the Alfred Caldwell Lily Pool, which is free to visit and recently reopened to the public.

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.

Step aboard City Cruises’ Seadog for a fun-filled journey through Chicago's history of ghosts, spirits, scandals and sins. As guests cruise along the Chicago River for 45 spooky minutes, expert—and costumed—docents weave stories of Chicago's darker side while cruising through the city's most iconic architecture. The cruise is BYOB, so be sure to bring a bevvy of your choice. 

A marquee program of the Chicago Cultural Alliance, Journey Chicago is a series of events taking place at cultural heritage centers across Chicagoland throughout October. Attendees can expect to experience unique cultural encounters, including Stitching Stories: Asia from East to West, Mid-Autumn Festival hosted by the Chinese American Museum of Chicago and Family Album Day, a genealogical experience presented in partnership by the Puerto Rican Arts Alliance and Bronzeville Historical Society.