chicago marathon 2017
Photograph: Jaclyn Rivas
Photograph: Jaclyn Rivas

The best things to do in Chicago this week

Find the very best things to do in Chicago this week, including cultural events, festivals and shows.

Shannon Shreibak
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Last updated October 6, 2025: We may be in the midst of an alarmingly summery spooky season, but Chicago's event calendar has more to offer than tricks and treats. If you’re looking to embrace the month’s Halloween themes, there’s no shortage of events for you: Jack’s Pumpkin Pop-Up is haunting Goose Island once again, Lincoln Park Zoo is hosting Fall Fest all month long and Island Party Hut's Fall Fest will dominate the Chicago Riverwalk this week. If you’re saving all your stamina for the weekend, spend the week prepping your wittiest Chicago Marathon sign to cheer on this year’s runners or kick back at Music Box Theatre’s annual horror movie marathon.

RECOMMENDED: Discover the best things to do in Chicago in October 2025

Time Out Market Chicago

Best events in Chicago this week

  • Things to do

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.

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  • Things to do
  • Avondale

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. 

  • Things to do
  • Suburbs

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. 

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  • Things to do
  • Millennium Park
  • Recommended

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.

  • Things to do
  • Event spaces
  • West Loop

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. 

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  • Attractions
  • Parks and gardens
  • Suburbs

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. 

The eighth annual Destinos: Chicago Latino Theater Festival returns to Chicago with a four-week lineup of live theater performances at venues throughout the city and Northwest Indiana. As usual, this year's lineup revolves around Latino-driven storylines, including several world premieres: Teatro Inovarte (a musical blending mariachi, ballet and queer love), Concrete Content (an immersive sketch show reimagining Latin futures via fake movie trailers) and more. 

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  • Sports and fitness
  • Yoga & Pilates
  • Streeterville
  • Recommended

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 levelsyou 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.

  • Things to do
  • Festivals

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. 

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  • Things to do
  • Festivals
  • North Center

Dovetail Brewery and Begyle Brewing Company are teaming up yet again for their annual Oktoberfest bash. Taking place outside in the shared lot between both breweries, the event features special beer tappings (alongside favorites from Dovetail and Begyle), live music and delicious bites from food trucks, including Happy Lobster, Soul & Smoke and the Fat Shallot. A $5 suggested donation benefits local food pantry The Friendship Center.

  • Museums
  • Museum Campus

Every Wednesday, the Adler stays open late from 4–10pm so that folks can visit after work or school—best of all, admission is free for Illinois residents. Escape the planet with exhibits about the first lunar missions, the solar system and more, plus sky shows in an immersive dome theater. 

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  • Kids
  • Lincoln Park

Get your fall feels on at Lincoln Park Zoo's annual free festival. You can snag a photo with a giant pumpkin, watch master gourd 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. 

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  • Things to do
  • Quirky events
  • Wrigleyville

Hosted at Stolen Saddle—one of Chicago's newest and largest country bars—this annual Halloween-themed extravaganza features photo ops galore as well an upstairs bar serving spooky cocktails like Freddy’s Tequila and Monster Mash. With the Cubs clinching a playoff spot this year, 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.

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  • Things to do
  • Literary events
  • Logan Square

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 concert with a constantly rotating bill—this month's lineup features Michael Hudson-Casanova’s Mystery School.

  • Things to do
  • Hyde Park

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. Designed for ages eight and up, the puzzles are engaging for the whole family, while also making this a perfect outing for couples and large groups. The escape room’s runtime averages 50 to 90 minutes, though puzzle-solving prowess may shorten or extend your stay in the museum.

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  • Things to do
  • Performances
  • Loop

The masterminds behind the irreverent long-running comedy show Drunk Shakespeare are unleashing their latest monster mash-up, “Drunk Dracula,” on the city just in time for spooky season. 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.

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  • Things to do
  • Festivals
  • Suburbs

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. 

  • Things to do
  • Loop

This annual festival assembles luminaries from the fields of politics, journalism and the arts for a multi-week series of programming across the city, with events ranging from lectures and discussions to screenings and musical performances. Not sure which events to hit? Some of this season's biggest speakers include Kate McKinnon, Margaret Atwood, Salman Rushdie and Nick Offerman. 

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  • Experimental
  • Uptown

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.

  • Art
  • Film and video
  • Recommended

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.

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  • Things to do
  • Festivals
  • Streeterville

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.

  • Comedy
  • Uptown
  • Recommended

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.

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