62nd Chicago International Film Festival
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Everything happening Sat Oct 17–Sun Oct 18.
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Get ready for an unforgettable night at the Downstairs Theatre At Steppenwolf Theatre – Chicago as we present “Topdog/Underdog – Chicago.” This powerful play delves into the complexities of brotherhood, identity, and…
$50 – $171
$46
The Wellness Retreat is a full-day wellness experience taking place October 17 at Northerly Island, built around one idea: where body, mind, and music meet.
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Chicago Farmers Markets sell fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds – at Chicago’s longest running farmers market on Daley Plaza and community markets in…
Free
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Following an in-studio performance on the WGN Midday News on Monday, Oct 5, Chicago singer-songwriter Stephen Kohler and percussionist Rob Klegon will perform a set of originals and covers as part of Madame Zuzu’s…
Free
If you’re looking for a fast, flexible Greeter experience, check out our Riverwalk InstaGreeter walks.
Free
Your Saturday brunch plans just got a whole lot better! Bad Momz of Comedy is taking over Comedy Bar on October 17 for a ONE-TIME-ONLY brunch & comedy show — and oh honey, this is NOT your average morning!
$25 – $35
Grab your dancing shoes and head downtown for the first-ever Loop Arts Fest.
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Marriott Theatre , Chicagoland’s longest-running musical theatre presents Come From Away , the internationally celebrated musical that was nominated for seven Tony Awards, including Best Musical, captured four…
$80 – $100
In celebration of Black Poetry Day, local Chicago poets from the Guild Literary Complex present readings from their favorite Black poets.
Free
The 10th Anniversary tour of the hit Broadway musical Waitress is coming to the James M.
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$35.00
Join Watson Adventures on a unique scavenger hunt for adults!
$19.00
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THE SWALLOW is set during a private singing lesson between a choral director and a new student.
$30.00
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$15 – $50
$40
Clarketoberfest at the Harley Clarke Mansion Oct. 16–18 brings three days of FREE fall fun, beer, food by Hatchet Burger, dancing, family festivities, and live music – including kid-favorite Jeanie B!
Free
Step into a world where light and dance intertwine in this breathtaking retelling of Sleeping Beauty.
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$35 – $45
$32
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Cheer on the Chicago Blackhawks at the United Center!
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Rising pop/country singer-songwriter Knox (Knox Morris) will perform live in Chicago on Saturday, October 17, 2026, at the House of Blues Chicago.
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Ben Schwartz is bringing his “Ben Schwartz & Friends” tour to Chicago for a night of unscripted improv comedy in the fall of 2026.
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Free
Catch Your Breath will perform live in Chicago on Saturday, October 17, 2026, as part of their “Not Broken Enough Tour”.
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HERITAGE SERIES is Park Hyatt Chicago’s signature series celebrating the traditions and craftsmanship behind the world’s most celebrated culinary and beverage cultures.
$540.00
Free
After wrapping the final season of Disney Channel’s top-rated show, LIV AND MADDIE , Joey Bragg has been incredibly busy establishing himself as a comedic leading man in Hollywood.
$25 – $35
Enjoy a 90-minute improv experience with The Second City, plus two cocktails and small bites for $110.
$110
$15 – $50
$25
Suki Waterhouse will conclude her North American tour in Chicago on Saturday, October 17, 2026.
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Alternative folk-pop band Judah & The Lion will bring their headline tour to Chicago on Saturday, October 17, 2026.
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Few contemporary violin concertos have made a splash with audiences like Arturo Márquez’s Fandango , which won a 2024 Latin Grammy.
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Celebrate Arthur Mitchell’s belief that ballet belongs to everyone with New York based Dance Theatre of Harlem, a company internationally acclaimed for redefining what ballet looks like in the 21st century.
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$22
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$40.00
Chicago-based dance company The Seldoms will kick off its 25th anniversary year at Studio5 Performing Arts Center with the world premiere of the new full-length All at Once, a Cubist-inspired performance work by…
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$34
$35.00
Stir Friday Night, Chicago’s premier and longest-running Asian American and Pacific Islander (AAPI) comedy organization, will return to the stage this fall for a two-night celebration of comedy featuring original…
$20
$40
Grupo Duelo is bringing their Gravedad Tour 2026 to the Rosemont Theatre on Saturday, October 17, 2026.
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The Sweetest Day Comedy Jam is coming to Chicago on Saturday, October 17, 2026, at 8:00 PM.
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$35 – $45
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$18
Get ready for 90-minutes of sketch comedy that flips classic horror on its head.
$20
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$46
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The Wicker Park Farmers Market will return on May 3 for its 26 th outdoor season.
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The Chicago Artisan Market – Fulton Market returns to historic Morgan MFG (401 N.
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Chicago Mosaic School’s first ever FALL Mosaic Fest! Sunday, October 18th 2026.
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Hidden history from deep research into fascinating stories, both famous and forgotten, with author and frequent TV “Talking Head” Adam Selzer
$22
If you’re looking for a fast, flexible Greeter experience, check out our Riverwalk InstaGreeter walks.
Free
Clarketoberfest at the Harley Clarke Mansion Oct. 16–18 brings three days of FREE fall fun, beer, food by Hatchet Burger, dancing, family festivities, and live music – including kid-favorite Jeanie B!
Free
Marriott Theatre , Chicagoland’s longest-running musical theatre presents Come From Away , the internationally celebrated musical that was nominated for seven Tony Awards, including Best Musical, captured four…
$80 – $100
This exhibit features photography taken by Deaf children and teens living in Somali and Sudanese refugee camps.
$45
Price: see link
Holy Ghost Bingo: God, Goblins, & Games is a Halloween-themed interactive comedy play written by Vicki Quade, one of the authors of the hit comedy, Late Nite Catechism.
$35
The 10th Anniversary tour of the hit Broadway musical Waitress is coming to the James M.
Price: see link
Go behind the scenes of winemaking at City Winery with Crush Camp, an interactive experience designed to get you closer to the craft.
$90.00
$34
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THE SWALLOW is set during a private singing lesson between a choral director and a new student.
$30.00
In their early piano trios, the teenage Shostakovich and Debussy showed the world their youthful exuberance.
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$40.00
STORIES WE WEAR: FASHION AS VISUAL NARRATIVE Join the Fashion Film Festival Chicago and the Evanston Art Center for an afternoon celebrating fashion as a powerful language of visual storytelling.
Free
$15 – $50
$35.00
$40
Identity Performing Arts 5th Anniversary – Celebrating 5 remarkable years of ingenuity, imagination, and shared spirit, on October 18th at the Edlis Neeson Theater at the Museum of Contemporary Art.
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Free
Foos Gone Wild is bringing The FOOS GONE WILD Tour 2026 live to Chicago on Sunday, October 18, 2026, at the House of Blues Chicago.
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Originally from St. Petersburg, Florida & currently based in Atlanta, Calimar White (AKA Agent Ratliff) is a hilarious standup comic, actor, influencer & business owner.
$25 – $35
$20
Lightly Toasted is a standup showcase at The Home Comedy Theater in the Lakeview neighborhood of Chicago every third Sunday of the month featuring up and coming and old school Chicago-based comics.
Free
$15
$15
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