The best things to do in Chicago this weekend

Every October, more than 45,000 runners hit the streets of Chicago and take a 26.2 mile tour of the city by foot. While it's too late to enter the race (and complete weeks of grueling training), you can join tens of thousands of spectators on the city's streets to cheer on participants as they make their way through the course. The start and finish line in Grant Park isn't open to the public, but you can head to neighborhoods like Pilsen, Chinatown, Boystown and Lincoln Park to join crowds of onlookers toting handmade signs, blaring music and encouraging all of the runners as they whiz by, or meet your runner at the reunite area of Grant Park starting at 9:30am. 

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.

Celebrate the close of summer in unforgettable fashion with Michelin-starred Chef Christian Hunter at the Time Out Market Rooftop. Throughout the night, guests will enjoy a seafood-forward menu highlighting the best of the season—dressed and grilled oysters, tomato tartare, playful small bites and thoughtful vegetarian options.

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. 

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.

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.

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. Some standout events include an indigo dyeing and shibori workshop; The Chicago Streetwear Expo; a runway show emphasizing sustainability; and Fleurotica, a fashion show featuring garments made entirely from plants, flowers and natural materials. 

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. 

To the surprise of no one, The Brewed—Chicago's premier horror-themed cafe—is deadly serious about spooky season. For one delightfully chilling day, The Brewed is hosting a family-friendly Halloween block party, complete with horror vendors, plentiful treats, a photo booth, DJs and much more. The event will be pregamed with a skeleton scavenger hunt. 

Hundreds of tricked-out cars and motorcycles line Loomis Street in Pilsen during this annual community festival, where you can take a look under the hood and watch classic rides bouncing around (with some hydraulic assistance). If you can tear yourself away from the automotive display, you can chow down on tasty tacos, shop for goods made by local vendors and listen to live DJs.

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.

Already got a jack-o'-lantern carved up at home? Ogle more than 7,000 unique, hand-blown glass pumpkins made by 18 artists during the Morton Arboretum's annual glass pumpkin patch. The multi-day event lets guests watch glass blowing demonstrations, meet the artists and buy their very own glass pumpkins.

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.

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. Seasonal snacks and drinks are available for purchase, in case all that wandering makes you hungry. 

Round up your family for a wild, multi-weekend Halloween festival perfect for all ages to enjoy. 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 capybaras, polar bears and gorilla—to pumpkins that they can play with, nibble on and smash. 

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. 

Get ready to unleash your inner Nancy Drew: Escape the Museum is returning to the Griffin Museum of Science and Industry. Participants will journey through a world of mystery, where each exhibit holds clues that lead closer to victory—and the honor of being crowned a member of the Guild of Alchemists. Curious about what the night entails? Check out our latest Instagram Reel for a full rundown.

A terrifying story set in the world of the Paranormal Activity film franchise, Felix Barrett (Sleep No More) and Chicago playwright Levi Holloway's latest endeavor promises chills and thrills. Here's what you need to know: James and Lou flee from Chicago to London in hopes of escaping the past, but they soon discover that it's not the city that was haunted—it's them.