The best things to do in Chicago this week

Want to get a free, behind-the-scenes look at the Chicago Board of Trade Building, Walt Disney's birthplace home, Orchestra Hall at Symphony Center and more iconic buildings throughout the Chicago area? You’ll have a chance to do so when the Chicago Architecture Center’s annual festival Open House Chicago returns to the city, opening up more than 170 architectural wonders across the city for free tours. 

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.

Raise the dead and celebrate spooky season with Chicago Athletic Association's quarterly skate night! Tear through the hotel's one-of-a-kind roller rink housed in a vintage gymnasium while Halloween-themed videos are projected on the walls and DJs All the Way Kay & J Bambii soundtrack the night. Whether you're a seasoned skater or a newbie, everyone is invited to lace up and join the fun. 

This annual arts-centric Halloween parade returns to State Street to cap off the City of Chicago's “Halloweek” festivities with an evening of colorful, family-friendly flair. Watch as participants from major cultural organizations, inspiring youth programs and aspiring artists in every field march down the downtown thoroughfare and prepare for a spectacle. 

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. 

360 Chicago and One Tail at a Time are teaming up for a blissful morning of yoga and puppies. Bring your mat for a 45-minute class; once the workout is over, you’ll have time to play with the pups and enjoy a coffee or mimosa. Stick around for as long as you’d like afterwards to take in the unparalleled views of the city. All proceeds benefit One Tail at a Time.

Some of the latest and greatest movies to hit the festival circuit arrive in the Midwest during the Chicago International Film Festival, which typically presents a lineup of around 100 dramas, documentaries, comedies and foreign films, plus 60 short film programs. In addition to CIFF's home base at AMC Newcity 14, the fest offers viewing opportunities across the city, with screenings at the Music Box Theatre, the Gene Siskel Film Center and more. 

Get your fill of frights at this undeniably spirited footrace. This one-of-a-kind nighttime adventure takes place on the grounds of Chicago’s largest cemetery, the sprawling 350-acre Victorian-era Rosehill Cemetery. Doubling down on the spooky factor, the entire course will be illuminated by candlelight, casting eerie glows on the statues and mausoleums along the way. Participants can choose between a chip-timed run or a more leisurely fun run/walk. The race will be followed by a celebration at Fireside Inn across the street. 

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. 

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. 

Love may not be blind, but is it deaf? Join comedian and host Allison Goldberg as she helps one lucky bachelorette find a prospective partner. Four men will compete in a series of games, which include scrolling through their phones and calling moms, to win a date. The only catch? They’ll have to do it all without speaking. Those in search of love themselves can also get in on the fun—a “wingcouple” roaming the audience will help match singles together. 

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. 

The Rocky Horror Picture Show's 50th Anniversary Spectacular Tour crash lands at The Chicago Theatre just in time for spooky season. Join the original Brad Majors (Barry Bostwick), Columbia (Nell Campbell) and Magenta (Patricia Quinn) for a screening of the original unedited film like you've never seen it before. Plus, enjoy a live shadow cast with audience participation, a memorabilia display featuring artifacts and wardrobe from the movie, a costume contest and more.

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. 

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. 

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.

SAUCED continues to liven up the market scene with its winter lineups, corralling over 50 local vendors selling handmade goods, jewelry, vintage clothing, prints and more treasures. Need to refuel? Snag food from the fleet of local vendors, or bust some moves to live beats from a rotating lineup of DJs.

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.

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.

This annual celebration of scary films returns to the Music Box Theatre for a monthlong marathon of frightening, thrilling and chilling movies. Catch screenings of films like Addams Family Values, Let The Right One In, and Bride of Frankenstein. 

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.

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. 

South Loop's Prairie Cannabis Dispensary is partnering with legendary tattoo artist David Allen—who's best known for his mastectomy tattoo series—for a Breast Cancer Awareness Month pop-up. During the event, Prairie Cannabis will donate 5% of gross sales from select brands to fund mastectomy tattoos. Attendees can also enter a raffle for a $300 floral tattoo: a rare chance to bypass Allen’s waitlist and access his work at a fraction of the usual cost. 

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.

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.

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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