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arts in the dark 2018, halloween parade
Photograph: Neal O'Bryan

The best things to do in Chicago this weekend

Find the best things to do in Chicago this weekend with our guide to concerts, exhibitions, festivals and more.

Zach Long
Written by
Zach Long
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It's the weekend of Halloween in Chicago, and you'll have no problem finding a place to show off your costume this weekend. The Arts on the Dark parade will march down State Street on Saturday night, while the Northalsted Halloween Parade takes over Halsted Street in Lakeview on Sunday evening. You can also attendee a throwback ’80s event at Time Out Market Chicago, see the new Candyman movie at Cherry Circle Room or attend a Halloween ball at the Congress Plaza Hotel. Plus, "The Office Experience" is welcoming guests (feel free to dress up in a suit) and you can throw on your dancing shoes as electro-pop duo Sylvan Esso headlines the Aragon. After you stock up on candy to give away (or eat yourself) catch up on the best things to do in Chicago this weekend.

RECOMMENDED: The best things to do in Chicago right now

Things to do this weekend in Chicago

  • Things to do
  • Festivals
  • Loop

After staging a social distance-friendly, "upside down" version of the annual parade last year—in which participants drove through a route thronged by costumed performers and puppeteers—Arts in the Dark returns to State Street for an art-centric procession along State Street to close out Chicago's "Halloweek" of holiday festivities (though the upside down version of the parade will still take place in Washington Park a few days earlier). 

  • Music
  • Dance and electronic
  • Uptown

There are few acts more exuberantly joyous than Sylvan Esso, the unlikely duo of singer Amelia Meath (formerly of acapella folk trio Mountain Man) and producer Nick Sanborn. Together, the pair makes slick, efficient electro-pop that balances emotionally resonant lyricism with danceable beats—your feet will start moving in spite of themselves. The group headlines the Aragon Ballroom on Halloween, joined by Colombian Canadian singer-songwriter (and winner of the 2017 Polaris Music Prize) Lido Pimienta.

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  • Things to do
  • Humboldt Park

In The French Dispatch—director Wes Anderson's latest pastel-hued, ultra-symmetrical flick, which is set for wide release on October 22—a group of zany journalists run amok in 1960s Paris while working for a New Yorker-esque magazine. You can get a taste of the movie's European whimsy in Chicago for a few weeks this fall at Café Le Sans Blague, a French Dispatch-themed menu takeover at Logan Square's Dayglow.

Visitors can choose from four themed coffee drinks: The Cycling Reporter (distilled coffee, juniper, lemon, alcohol-free champagne); The Concrete Masterpiece (espresso, chicory, cream, demerara sugar, cinnamon); Revisions to a Manifesto (black French roast de Belleville); and The Private Dining Room of the Police Commissioner (hibiscus, flash brewed coffee and verjus rouge, a type of juice made from unripe grapes). Purchase of each drink—which ranges from $6–$12—comes with your choice of The French Dispatch merch, including enamel pins, totes, T-shirts, notebooks, pencil cases and copies of The French Dispatch magazine (while supplies last). 

The takeover runs through November 15. Don't forget to snap a Wes Anderson-style symmetrical pic of your drink before you leave! 

  • Movies
  • Horror
  • Loop

Nia DaCosta's recent Candyman revival shot a scene in the Cherry Cricle Room inside the Chicago Athletic Association, so the restaurant is hosting a special Halloween night screening of the contemporary horror film. Guests can choose between two packages, one that provides a light meal and drinks, and another that will set you up with some popcorn and a drink. We don't recommend saying any names while standing in front of the bathroom mirrors, because the Chicago Athletic Association is definitely old enough to be haunted.

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  • Things to do
  • Festivals
  • Boystown

Wanna see some of the best Halloween costumes in the city? Head to Northalsted (formerly known as Boystown), where a group of dedicated cosplayers shows off their creations at this annual procession. You'll find drag queens, kids, parents and pets marching in the Northalsted Halloween Parade, which typically features impressive group costumes and dancers performing all the moves to Michael Jackson's "Thriller." 

  • Music
  • Rock and indie
  • North Center

Local weirdo marching band Mucca Pazza brings its mismatched uniforms, horns, cellists, guitarists, drummers and enthusiastic cheerleaders to Martyrs', squeezing onto the venue's stage. Expect a characteristically ecletcic set from the expansive collective, as it explores everything from Balkan music to big band arrangements.

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  • Things to do
  • Quirky events
  • Wrigleyville

If you're reading this, you're probably too old for trick-or-treating—but that doesn't mean you can't treat yourself this Halloween season. For a few weeks this fall, Deuce's Major League Bar in Wrigleyville will transform into Nightmare on Clark Street, a spooky pop-up complete with themed cocktails, festive snacks and plenty of ghoulish decor perfect for those among the 21+ crowd looking to celebrate the holiday.

Hosted by the same team that puts on well-loved holiday pop-ups like Santa Baby and Rudolph's, Nightmare on Clark Street will feature drinks like Cookies-N-Scream (RumChata, creme de cacao and vanilla vodka with an oreo rim and eyeball candies) and Michael Meyer's Michelada (basically a standard michelada outfitted with a "bloody" syringe). Hungry? You can pair your beverage with bites like apple pie waffles, s'mores brownies or a worms-and-dirt milkshake. And of course, the pop-up's autumn-themed decor offer bountiful opportunities for photo ops—get dressed up and feel free to snap a few pics.

Reservations for Nightmare on Clark Street are free and can be made on the Deuce's website. Keep in mind that reservations are for up to 1.5 hours, can be for no more than six people, and that you'll need to adhere to the City of Chicago's masking guidelines. 

  • Time Out Market
  • West Loop

Need Halloween eve plans? Once you've finished your horror movie marathons and haunted house excursions, swing by Time Out Market Chicago as the food hall travels back in time to the ’80s, complete with Pop Rocks-rimmed cocktails and an era-appropriate soundtrack from DJ Rhea. Guests can snap photos in front of giant Lite Brite, play Pac-Man or set a high score on a Super Mario Bros. arcade cabinet. And don't forget to wear your costume, take a photo of yourself at the Market and tag @timeoutmarketchicago—we'll be awarding Time Out Market gift card to the evening's best-dressed guests.

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  • Nightlife
  • Irving Park

This gathering of vampires from across the region at Twisted Hippo Brewery culiminates in a vote for Chicago's newest Vampire Queen. Throughout the night, watch classic vampire films, catch live burlesque performances and order from a cash bar (tickets include one complimentary drink and one vote for the Queen). Note: Proof of vaccine and vampire attire (including fangs) are required for entry. 

  • Music
  • Folk, country and blues
  • River West/West Town

The Cosmic Country Showcase celebrates twangy tunes delivered with psychedelic trappings, dressing up the Hideout's stage to present a wonderfully strange variety show. The latest edition of the event celebrates the first openly gay country album, released by Lavender Country and reissued by Paradise of Bachelors. Frontman Patrick Haggerty headlines two Cosmic Country shows during Halloween weekend, playing tunes from the pioneering record alongside regulars like Andrew Sa and a lineup of special guest musicians, comedians and performers.

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  • Time Out Market
  • West Loop

Head to Time Out Market Chicago with your kids for a Halloween Book Club and Storytime, presented with the help of Connections Academics. Stories will be read by Anna Tewell who is a former teacher and the current Director of Connections Chicago. This Halloween Book Club will be filled with fun and engaging stories about the best parts of spooky season. Kids are encouraged to celebrate the holiday by wearing their costumes!

  • Nightlife
  • Cabaret and burlesque
  • West Loop

Looking to get weird this Halloween weekend? Head to Little Wild, the new-ish rooftop bar at Ace Hotel Chicago, for a spooky three-floor bash complete with burlesque and illusionary performances, tarot readings, a costume contest and more. A $25 ticket grants you entrance and one free drink ticket, but you can also opt for pricier packages that include table reservations (ranging up to the $666 VIP group table, which comes with bottle service, front row seats and tarot readings). FYI: You'll need to be wearing a costume to get in. 

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  • Nightlife
  • Cabaret and burlesque
  • Wicker Park

Arts incubator Haven Chicago hosts this two-night, Rocky Horror Picture Show-themed Halloween extravaganza at The Den Theatre. Catch drag performances from Ramona Slick, Travis Fiero, Vanda LaRose and more alongside live shadowcast performances, plus burlesque, belly dancing, contortionist and pole dancing shows. You'll also find a vendor fair, nail art, tarot readings, a Polaroid photo booth and additional spooky activities—and don't forget to wear your best costume for a chance to win a cash prize. 

  • Nightlife
  • Nightlife
  • Loop

The Congress Plaza Hotel hosts its annual Haunted Halloween Ball, inviting costumed attendees to spend a night dancing and celebrating in a building that some claim is haunted. Guests will be able to mingle with spirits and the not-yet-deceased in the hotel's ballrooms, which sport spooky decorations, zombie cocktail servers, go-go dancers and vampire bellmen. You'll have access to multiple cash bars, great views of the city's skyline and the chance to enter a costume contest and compete for $2,000 in cash and prizes.

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  • Nightlife
  • Loop

Celebrate Halloween at this lavish party hosted by LondonHouse Chicago, where you'll find a premium bar and live DJs spread between the LH on 21 Lounge, Etoile Ballroom and rooftop space. Stick around for the costume contest that commences at midnight—the first place winner will receive an overnight stay at the hotel and two tickets to the upcoming New Year's Eve party. 

  • Theater
  • Logan Square

The Latina comedy collective Ratas De Dos Patas celebrates Día De Los Muertos with this immersive, bilingual theater experience at Hairpin Arts Center complete with a live show, living ofrendas, beer from Cervecería Cruz Blanca and a market of Latin-owned businesses. Doors open at 7pm and the show will run from 8pm to 9:30pm. 

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  • Things to do
  • Festivals
  • Suburbs

If you really want to scream, head to Six Flags Great America where you can ride roller coasters in the dark and visit six haunted houses. Escape evil clowns, delve into the gates of hell, and explore a cursed manor. As you wander the park you’ll encounter demons, zombie lumberjacks, nightmarish fairy tales, and creepy circus performers. You can add to the frightful fun by snacking on Halloween-themed treats, watching a nightly parade and catching shows featuring live music, dancing and illusions.

  • Nightlife
  • Streeterville

You'll have plenty of room for ghoulish fun at this Halloween party hosted by Offshore, the massive rooftop space at Navy Pier. Tickets to the costumed event include a four-hour bar of bottomless drinks and light bites. Come wearing your best costume—the winner of the contest will receive a $1,000 cash prize and a one-night stay at the Sable Hotel. 

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  • Music
  • Rap, hip-hop and R&B
  • Lincoln Park

Evanston rapper, producer and songwriter Kweku Collins takes the stage at Golden Dagger four times in September and October as part of a fall residency at the Lincoln Park venue. Joined by a different special guest for each performance (Ajani Jones, Creaturefight, Orisun and OddCouple), Collins will debut tracks from his unreleased new album. Hopefully he'll find some time to delve into his past work, including his emphatic cover of the Yeah Yeah Yeahs' ballad “Maps” that graced his 2017 EP, grey.

  • Time Out Market
  • West Loop

Need somewhere to take the kids on Halloween? Join us for a special storytime with Spider-Man and Ariel, where the costumed characters will entertain the little ones with captivating tales. The storytime will be followed with a meet and greet with the characters and trick or treating at the vendor stalls throughout the Market, so come prepared to celebrate all things Halloween!

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  • Museums
  • History
  • Skokie

Tracing the contemporary gay rights movement back to the June 1969 police raid of the Stonewall Inn in New York City, the Illinois Holocaust Museum's hosts an exhibtion that documents a continuing struggle for equality. On loan from the Newseum, “Rise Up: Stonewall and the LGBTQ Rights Movement,” collects more than 85 artifacts, such as posters from Harvey Milk’s campaign for public office in San Francisco and the gavel Nancy Pelosi used to announce the repeal of “don’t ask, don’t tell.” Visitors will learn about the history of the LGBTQ community through pivitol moments in history and in popular culture.

  • Things to do
  • Exhibitions
  • Magnificent Mile

Calling all The Office fanatics: The same team that created "The Friends Experience" is back with another nostalgic pop-culture experience that will make you feel like a Dunder Mifflin employee. Spread across two floors, the pop-up features 17 rooms that recreate sets from the show, including the Scranton Business Park workplace (which features Michael's office, Pam's reception desk and Ryan's closet) and Schrute Farms. Guests will be able to ecreate moments like Kevin's chili spill and the Dundie Awards—and you'll also find a few original props and costumes on display.

Don't forget to stop by a gift shop that's dressed up like the Warehouse, featuring merch like "World's Best Boss" mugs, sweatshirts that say "Nard Dog" and staplers (Jello not included). The gift shop will be open to both ticketed and non-ticketed guests, so even those who don't spring for the photo-friendly experience have a chance to buy some branded shirts and tchotchkes.

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  • Movies
  • Horror
  • Lower West Side

The Music Box of Horrors 24-hour movie marathon is back on the big screen at the Southport theater this year (on October 23 and 24), but organizers are also reviving the month-long drive-in screening series that took its place last year. Once again, you'll be able to pile your friends into a car and catch single and double features at the Chi-Town Movies Drive-In throughout October. Of course, the lineup of films is terrifyingly good.

This year's themes include Nü-Metal Mondays (films with a late ’90s soundtrack), Thirsty Thursdays (vampire movies), Friday Night Double Features (two movies!), Rip-Off Saturdays (an original movie followed by its imitator), and Serial Killer Sundays (real-life monsters).

Highlights of the lineup include psychedelic ’70s flick The Velvet Vampire, a Japanese horror double feature of Ringu and Dark Water, Hellraiser and its shot-for-shot Indonesian remake Roh, and Wes Craven's underappreciated social satire The People Under the Stairs.

Just like last year's Music Box of Horrors drive-in screenings, you can expect specialized movie intros, hilarious pre-show content, filmmaker Q&As and vendors selling their spooky wares. If you don't think that you can stay up for 24 hours of horror movies at the Music Box's marathon, this is a pretty great alternative. Admittance for each screening begins 30 minutes before showtime.

  • Movies
  • Horror

The Chicago Park District's beloved summer screening series Movies in the Parks might be over, but you can still catch a few more free flicks at select parks this October thanks to Campfire Horrors, an outdoor horror movie series featuring spooky classics and campfires for roasting marshmallows.

Screenings will be held at 7pm on every Friday of October at Northerly Park, as well as on select Saturdays at Dvorak Park, North Park Village Nature Center and Sherman Park. Unlike its summertime counterpart, Campfire Horrors features a slightly more robust selection of R- and PG-13-rated movies (The Birds, Scream and Little Shop of Horrors) along with family-friendly titles like Hocus Pocus and The Nightmare Before Christmas.

Plan to dress warmly and bring a blanket or chair to settle in for the movie. Campfires and marshmallow roasting supplies will be on hand if you want to make a snack while you watch, though you'll need to wear a face covering when you're not eating and maintain social distancing. Check out the full Campfire Horrors schedule below, and happy spooky season! 

The Birds (Friday, October 8 at 7pm, Northerly Island)

Hocus Pocus (Saturday, October 9 at 7pm, Dvorak Park)

Scream (Friday, October 15 at 7pm, Northerly Island)

The Nightmare Before Christmas (Saturday, October 16 at 7pm, North Park Village Nature Center)

Little Shop of Horrors (Friday, October 22 at 7pm, Northerly Island)

Scoob! (Saturday, October 23 at 7pm, Sherman Park)

Beetlejuice (Friday, October 29 at 7pm, Northerly Island)

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  • Things to do
  • Exhibitions
  • Streeterville

Get lost in a world of Wockets and Truffula Tree contained within this immersive experience, inspired by the literary works of Dr. Seuss. Bringing to life the characters and landscapes of books like The Cat in the Hat and The Lorax, "The Dr. Seuss Experience" is filled with a series of rooms where guests can interact with characters and snap photos. At the center of the pop-up, there's a maze inspired by Oh, the Places You’ll Go! made up of thousands of suspended balloons. Taking over 25,000 square feet on the street level of Water Tower Place, this experience is great for kids—or for embracing your inner-child.

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  • Things to do
  • Lincoln Park

The Chicago History Museum commemorates the 150th anniversary of the Great Chicago Fire of 1871, exploring how the tragic event transpired and how it changed the city for decades to come. The family-friendly exhibition examines the details of the three-day blaze, exploring how the Irish immigrant O’Leary family was blamed for the fire and tracing the path of destruction (and 100,000 homeless residents) that the incident left in its wake. Featuring more than 100 artifacts from the museum's collection—including items that were damaged in the fire—"City on Fire: Chicago 1871" also showcases a reproduction of a cyclorama painting depicting the fire's path that was originally displayed at the World's Columbian Exposition of 1893.

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  • Art
  • Photography
  • Grant Park

Explore the small-but-mighty works of photographer André Kertész, who arrived in Paris in the fall of 1925 with a camera and what was left of his savings. Over the next three years, the majority of the photos he produced were printed on postcard paper, making them easy to share with friends and benefactors. Exhibiting a collection of these small-scale works, the Art Institute's latest exhibit explores Kertész's output in the years before he graduated to international exhibitions and magazine spreads.

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  • Things to do
  • Quirky events
  • Wrigleyville

If you're reading this, you're probably too old for trick-or-treating—but that doesn't mean you can't treat yourself this Halloween season. For a few weeks this fall, Deuce's Major League Bar in Wrigleyville will transform into Nightmare on Clark Street, a spooky pop-up complete with themed cocktails, festive snacks and plenty of ghoulish decor perfect for those among the 21+ crowd looking to celebrate the holiday.

Hosted by the same team that puts on well-loved holiday pop-ups like Santa Baby and Rudolph's, Nightmare on Clark Street will feature drinks like Cookies-N-Scream (RumChata, creme de cacao and vanilla vodka with an oreo rim and eyeball candies) and Michael Meyer's Michelada (basically a standard michelada outfitted with a "bloody" syringe). Hungry? You can pair your beverage with bites like apple pie waffles, s'mores brownies or a worms-and-dirt milkshake. And of course, the pop-up's autumn-themed decor offer bountiful opportunities for photo ops—get dressed up and feel free to snap a few pics.

Reservations for Nightmare on Clark Street are free and can be made on the Deuce's website. Keep in mind that reservations are for up to 1.5 hours, can be for no more than six people, and that you'll need to adhere to the City of Chicago's masking guidelines. 

  • Art
  • Photography
  • Loop

There are more guns than people in America, making it the most heavily-armed country in the world. “American Epidemic: Guns in the United States” collects photos from 10 different photographers that contemplate the violence, trauma, racism and other issues that arrise in a society where shootings are commonplace. You'll find images by Carolyn Drake, Nancy Floyd, Stephen Foster, Andres Gonzalez, Félix González-Torres, Deborah Luster, Zora J Murff, Renée Stout, and Hank Willis Thomas and Kambui Olujimi in the exhibit. If you're going to visit, make sure to secure a timed reservation via the Museum of Contemporary Photography's website. 

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  • Time Out Market
  • West Loop

Want to watch the Bears play on a big, big screen? Time Out Market Chicago's screen is 32 feet wide by 6 feet tall, and you'll be able to watch every single game on it. And in addition to chicken wings, stacked burgers and saucy barbecue platters, you'll also be able to take advantage of select half-price draft beers and $20 beer buckets during every matchup. Plus, if a game falls on a Sunday, $10 Bloody Marys will also be available. There's no need for a reservation—just show up ready to feat while you cheer on the Bears!

  • Art
  • Painting
  • Streeterville

Los Angeles–based artist Christina Quarles paints bodies, but not in the way you'd expect. Instead of straightforward studies of the human form, her canvases demonstrate a disregard for gravity and anatomy that finds torsos, limbs and faces arranged in surreal ways. This Museum of Contemporary Art show is her largest exhibition yet, focusing on her output over the past three years, including a large-scale installation that incorporates illusions.

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  • Things to do
  • River North

Dinner comes with a side of frights at this haunted—and totally dark—dining experience headed to Chicago for Halloween season. Here's how it works: Diners enter a pitch-black room, meant to heighten the senses while eating, at Masq inside the Hubbard Inn for a 90-minute, three-course meal with wine pairings, available in meat, fish and vegan options. Each course is dished out by a masked (and spooky) server clad in night vision goggles. You'll be asked to guess what's in each meal, but don't be surprised if the scary environs lead to some degree of distraction. Don't forget to dress up in your Halloween costume! 

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  • Things to do
  • Festivals

Want to get a free, behind-the-scenes look at the Bahá'í House of Worship, Herman Miller Showroom, Chinese American Museum of Chicago and more than 100 other architectural gems throughout the Chicago area? You'll soon have a chance to do so: After offering a virtual version of its programming in 2020, the annual architecture festival Open House Chicago returns this October with in-person tours, online lectures and an expanded version of its app for independent exploration throughout the city, featuring self-guided tours of thematic architecture "trails" in different neighborhoods of Chicago. 

The program kicks off on September 28 with Chicago Architecture Center members-only previews before launching on-app programming on October 1 (available for download on Apple or Android devices). Using the app, folks can navigate a series of self-guided, multi-site tours—called "trails—which include topics like the Obamas in Hyde Park and the 150th anniversary of the Great Chicago Fire. The app will also include a guide to sites available for in-person visits, plus info on other city attractions, and will be available through October 31.

In-person tours will take place during the weekend of October 16–17, with tours spread throughout more than 30 neighborhoods and a handful of suburbs. New sites this year range from the newly-opened Pullman National Monument Visitor Information Center to the Sable Hotel at Navy Pier; in addition, catch returning favorites such as the Alfred Caldwell Lily Pool, Glessner House, International Museum of Surgical Sciences and more. 

Throughout October, you can also check out a series of free virtual lectures on different architectural and historical topics, including "Revisiting Learning from North Lawndale" and "How the Great Fire Changed Chicago." Plus, the CAC continues to host "Helmut Jahn: Life + Architecture"—a look at the work of the iconic Chicago-based architect, who died earlier this year. 

The festival will run throughout the entire month of October—you can read through an up-to-date list of sites here. FYI: While no advance registration is required for on-site visits, some sites may require proof of COVID-19 vaccination or a negative test to enter, so check CAC's website before planning your visit. 

  • Theater
  • 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. Returning to in-person programming (attendees must be vaccinated and masked) after more than a year spent in the virtual realm, the company's signature show is more unpredictable than ever, 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.

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  • Things to do
  • Festivals
  • River West/West Town

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, thousands of pumpkins, ax 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 three bars or go axe-throwing. 

  • Things to do
  • Exhibitions
  • Streeterville

You'll find nearly 1,000 glowing pumpkins spread throughout Navy Pier at the attraction's month-long Pier Pumpkin Lights event, which places elaborate jack-o'lanterns across the Pier's outdoor facilities. Wander around the glowing, spooky spectacles and catch deals from the Pier's many restaurants and bars, plus other seasonal festivities fit for the whole family. 

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  • Art
  • Contemporary art
  • Loop

Curated by School of the Art Instiute of Chicago faculty members Giovanni Aloi and Andrew S. Yang, “Earthly Observatory” collects artworks that examine how humans engage with and form an understanding of the planet that we live on—from its natural wonders to man-made objects. Visitors can take in works like an elongated horse skeleton created by artist Zoé Strecker and a red "carpet" crafted from Oklahoma soil by artist Rena Detrixhe. Drawing on elements of art, design and natural sciences,“Earthly Observatory” is an exhibit that melds creativity and critical thinking. All visitors to the SAIC must register in advance.

  • Things to do
  • Quirky events
  • River North

Snag a treat and some decorative gourds at the month-long, 5,000-square-foot JoJo's Pumpkin Patch pop-up, a festive patio adjacent to JoJo's Shake Bar in River North where you'll find hay bales, festive lights and "pumpkin domes" outfitted with tables for dining and hanging out. 

Guests can enjoy a menu of special seasonal dishes, including caramel apples, pumpkin pie, apple pie, spiked ciders and hot chocolate. There's also a decadent Pumpkin Patch Shake— topped with a slice of pumpkin pie, a taffy apple, roasted marshmallow and a Reese's pretzel—plus cocktails like the Caramel Apple Mule and Pumpkin Spiked Latte. And if you need a big orange gourd to bring home, you can purchase one here. Cheers to fall! 

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  • Art
  • Film and video

Projecting a 25-story-tall video installation on the side of the Merchandise Mart, Art on theMart's latest program showcases the work of conceptual artist Barbara Kruger. Throughout the fall, you'll be able to see Kruger's video piece "Untitled (Questions), 1990/2021," which projects a series of questions across the face of the building in a bold font. The presentation conicides with Kruger's new exhibition at the Art Institute of Chicago, "Thinking of You. I Mean Me. I Mean You."

Art on theMART's array of 34 digital projectors display the 30-minute program at 7:30 and 8pm every evening. The show is best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

  • Art
  • Contemporary art
  • Grant Park

Don't call this one a retrospective. Yes, the Art Institute's exhibition of Barbara Kruger's work encompasses four decades of her career, but "THINKING OF YOU. I MEAN ME. I MEAN YOU." isn't stuck in the past. Instead, the display takes Kruger's vintage works and presents it alongside new pieces that build upon them, unlocking new context and meaning. Spread throughout the museum, guests will find rooms wrapped in Kruger's imagery, installations in the Regenstein galleries and pieces that inhabit the exterior walls of the museum (as well as billboards, bus stops and storefronts around Chicago). Expect to see Kruger's biting sense of humor on display—often spelled out in big, bold letters.

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  • Things to do
  • Festivals

Every two years, Chicago becomes a global hub of architecture and design during the Chicago Architecture Biennial. This year's edition takes place across three months, filling vacant lots with site-specific architectural projects and presenting a pair of exhibitions at the Bronzeville Artist Lofts and the Graham Foundation. The theme of this year's Biennial is "The Available City," presenting projects and conversations that respond to and expand upon the question of "who gets to participate in the design of a city?"

Highlights of this year's programming include a circular outdoor meeting space designed by Matri-Archi(tecture) in a lot on 63rd Street in Woodlawn and a pair of exhibitions at the Bronzeville Artist Lofts and the Graham Foundation that feature projects by a global group of architects and designers, hailing from New York, Porto, Paris and Beijing. Plus, a series of Activation Weekends will activate the various Biennial installations throughout the city, welcoming performers, experts and cultural programming.

Stay up-to-date on the latest programming and activations by visiting the Chicago Architecture Biennial website.

  • Museums
  • Natural history
  • Museum Campus

One of the Field Museum's most popular traveling exhibitions (which debuted in Chicago in 2014) returns home, using interactive displays to showcase how the bodies of animals operate much like machines. Visitors can use a pump to see how a giraffe's heart is able to send blood all the way up its neck or take in footage of a cheetah running to see how it's able achieve incredible speeds.

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  • Art
  • Street art
  • River North

It's been more than a decade since a genuine Banksy work was spotted in Chicago, but you can see 80 of the street artist's creation in this exhibition. "The Art of Banksy" is an unauthorized show collecting canvasses, screen prints, sculptures and other pieces that the enigmatic artist made between 1997 and 2008, including the now-famous images "Flower Thrower" and "Girl with Balloon."

Presented by the same folks behind the "Immersive Van Gogh" experience, the opening ot the "The Art of Banksy" has been stymied by a recent venue change—the show was originally scheduled to open at the Epiphany Center of the Arts, but organizers and the owners of the West Loop venue parted ways. Now, the exhibition will be housed on the fourth floor of 360 N State Street, in the same building that hosts the Museum of Broadcast Communications.

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  • Art
  • Architecture
  • Loop

Best known locally for designing the James R. Thompson Center and Terminal 1 (including its popular neon-lit walkway) at O'Hare International Airport, German-born architect Helmut Jahn spent his career pursuing distinctive visions. In light of his recent passing after being struck while riding a bicycle in suburban Chicago, the Chicago Architecture Center presents a career retrospective, exploring his work and the enduring legacy of the structures he designed.

Showcasing a collection of personal and professional items loaned by Jahn’s family and firm, the exhibit traces his path, beginning with his days as a student at the Illinois Institute of Technology. Guests can take in photography, models and sketches of Jahn's most famous designs, including the Sony Center in Berlin and the Michigan City Public Library. You'll also get a peek at more recent projects like Chicago's 1000M and the Pritzker Military Archives, which is currently under construction in Somers, Wisconsin.

  • Art
  • Contemporary art
  • Streeterville

The Museum of Contemporary Art Chicago presents a survey that encapsulates two decades of work by Pakistani artist Bani Abidi, a former student at the School of the Art Institute of Chicago. Known for her video, photography and sound works, Abidi satirizes displays of power and nationalism as she explores the geopolitical relationship between India and Pakistan as well as the historical power struggles of South Asia. The exhibit takes its name from Abidi's watercolor series "The Man Who Talked Until He Disappeared," which depicts writers, political leaders and bloggers from Pakistan that have disappeared over the past decade.

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  • Theater
  • Experimental
  • Lake View

Since 1997, a trio of performers covered in bright blue paint have headlined the Briar Street Theater in Lakeview. The Blue Man Group's show has evolved throughout the years, incorporating new compositions, narratives and state-of-the-art technology. But at its core, this production is all about combining percussion, music, physical comedy and buckets of brightly-colored paint in ways that make you want to jump out of your seat and dance along to the beat.

  • Things to do
  • Exhibitions
  • Loop

Looking for a less conventional kind of escape room to check out in Chicago? Visitors are tasked with deciding the fate of a man accused of murder in this new, multi-room immersive experience in the South Loop, which uses projections, live actors and other tools to challenge the internal biases involved in our day-to-day decisions as well as the criminal justice system.

Located inside the Roosevelt Collection Shops, the 90-minute experience takes visitors through a weaving set of storylines and sets in a Clue-like pursuit of figuring out who's responsible for a crime; in the process, the exhibit explores elements racism, ageism, classism and other social issues that affect the criminal justice system. Visitors will have an hour to examine the case and come to a decision and then an additional 30 minutes for photo opportunities. 

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  • Art
  • Design
  • Loop

Comic artist and author Chris Ware and historian Tim Samuelson curate an exhibition devoted to the early days of the comic strip. Showcasing work from the period of 1880 to 1960, the exhibit includes early strips that ran in newspapers as well as work by African-American cartoonists and publishers. The exhibit also pays tribute to Frank King, who penned "Gasoline Alley," creating one of the very first autobiographical comics based on real Chicagoans and the neighborhoods they lived in. If you've already seen the Museum of Contemporary Art's “Chicago Comics: 1960s to Now” exhition, this show will give you an even deeper understanding of the artforms ties to the Second City.

  • Time Out Market
  • West Loop

Every Sunday from 11am to 3pm, Time Out Market Chicago's chefs offer a variety of delicious brunch dishes, from Hangover Ramen with shrimp and smoked pork to a stack of Buttermilk Pancakes layered with whipped mascarpone. Order as much as you want, grab a mimosa pitcher from the bar and stick around from 1 to 3pm for a set of tunes from the Chicago Soul Jazz Collective. 

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  • Comedy
  • Uptown

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.

  • Art
  • Old Town

Step inside of Starry Night and The Bedroom in Arles with the help of more than 75 digital projectors in this high-tech exhibition that explores the work of Vincent Van Gogh. Designed by the Italian creative team that worked on the "Atelier des Lumières" exhibitions in Paris, "Immersive Van Gogh" covers 35-foot walls with animated versions of the Dutch painters work, accompanied by a score that blends electronic and classical compositions. The exhibition takes up residence in the Germania Club Building in Old Town, which will go by the name Lighthouse ArtSpace Chicago and host additional interactive art exhibitions in the coming years.

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  • Theater
  • Circuses & magic
  • Loop

Enjoy dinner and show on the 14th floor of the Cambria Hotel at Teatro ZinZanni, a 2.5-hour experience that combines circus acts, comedy, cabaret and a meal curated by Debbie Sharpe—the Goddess of The Goddess and Grocer. The show takes place in an ornate, circular theater (designed to resemble a Belgian mirror tent) where the audience surrounds the stage. Guests dig into a four-course meal while watching as comedians, aerialists, acrobats, singers and dancers perform amazing feats and catchy tunes. It's somewhere between Cirque du Soleil and a traditional cabaret show, with restaurant-quality refreshments.

  • Things to do
  • Loop

The Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady is one of the most popular attractions in Chicago. Enjoy a tour with your friends and family and soak up the sunshine while hearing the secrets and stories behind Chicago’s riverfront buildings, as told by expertly trained CAC docents.

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  • Shopping
  • Markets and fairs
  • West Loop

Originally established in the late 1800s, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. The market introduced the Maxwell Street Polish sausage, provided a venue for rising Chicago blues musicians and was immortalized in a scene in The Blues Brothers. These days, the market sets up on nearby Desplaines Street (between Roosevelt and Howard) every Sunday, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and occasional performances by local bands and dance troupes. Don't let the cold or wet weather scare you away—the Maxwell Street Market takes place outdoors year-round.

  • Comedy
  • Stand-up
  • Logan Square

Now housed in the space on Milwaukee Avenue in Logan Square, the country's longest countinuously running independent comedy showcase continues every Friday and Saturday night. Boasting alumni like Cameron Esposito, Kumail Nanjiani and Hanibal Buress, this stand-up show will introduce you to fresh new faces that may end up starring in Marvel movies or becoming podcast mainstays. Snag an affordable ticket, avoid the two-drink minimum and prepare to laugh your ass off.

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  • Sports and fitness
  • Running

Go for a run and replentish your electrolytes with a beer during this series of 5K walks and runs, that take place at breweries throughout Chicago (and beyond). All of the Illinois Brewery Running Series events are untimed fun runs, more focused on camaraderie than competition. Participants at each event recieve a free beer, glassware or seasonal swag item, plus access to post-run events that feature live music, food, goodies from sponsors and giveaways. Check out the complete schedule of events on the Illinois Brewery Running Series website.

  • Art
  • Sculpture
  • Suburbs

See five towering sculptures by South African artist Daniel Popper at the Morton Arboretum's new outdoor exhibition, which spreads the 15- to 26-foot-tall works throughout the natural area. Made of glass-reinforced concrete, wood, fiberglass and steel, the one-of-a-kind pieces in "Human+Nature" depict human figures that evoke the natural landscape they're set amid, including a pair of 36-foot-long hands reaching out from a grove of oak trees and a maternal figure that springs up amid magnolia trees.

Access to "Human+Nature" is included as part of timed-entry admission to the Morton Arboretum, and there's a map that will allow you to easily plan your visit and spot all five of the sculptures along the way.

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  • Art
  • Photography
  • Lincoln Park

The Chicago History Museum welcomes a fascinating multimedia exhibition of more than 65 pieces from the celebrated street photographer. Known for beautifully capturing everyday moments, each of the shots on display here was taken when Maier was a suburban Chicago nanny from the ‘50s to the ’70s. Most of them have never been on display, and feature alongside film clips, quotations, and sound bites that help to bring Maier’s incredible work further to life.

‘Vivian Maier: in Color’ opens May 8 2021. Admission is included in the Chicago History Museum entry price. For more information head to www.chicagohistory.org/exhibition/vivian-maier-in-color

Written by Time Out. Paid for by Chicago History Museum

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  • Art
  • Installation
  • West Loop

The home of Chicago's only Infinity Mirror Room (created by Japanese Yayoi Kusama) is open to the public once again, presenting a new collection of one-of-a-kind art installations alongside some old favorites. New additions to WNDR Museum include a multi-sensory experience from S̶A̶N̶T̶IA̶G̶O̶X that uses artificial intelligence, sounds, visuals and scents, as well as an installation called I Heard There Was a Secret Chord that allows guests to become part of an evolving virtual choir.

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