What are our picks for the best events happening in Chicago worth your time this weekend (October 16-19)? This is the Week to Weekend Guide you need. Ready to make this weekend count? From art+culture events, fashion celebrations and spooky scenes we’ve curated the best of things to do this weekend in Chicago so you can skip the scroll.
61st CHICAGO INTERNATIONAL FILM FESTIVAL
October 16-26 | Varies
AMC NEWCITY 14 | Gene Siskel Film Center | Chicago History Museum| Music Box Theatre |
Chicago International Film Festival was started in 1964 by filmmaker and graphic artist Michael Kutza to provide an alternative to the commercial Hollywood movies that dominated the city’s theaters. Seeking out the best in international cinema, the Festival has opened windows to a world of film previously or otherwise unavailable in Chicago.
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THE LION KING
October 3-19 | Time Varies
Cadillac Palace Theatre | 151 W. Randolph Street
Giraffes strut. Birds swoop. Gazelles leap. The entire Serengeti comes to life as never before. And as the music soars, Pride Rock slowly emerges from the mist. This is Disney’s THE LION KING. The show is suitable for ages 6 and up.
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THEASTER GATES ‘OH YOU’VE GOT TO COME BACK TO THE CITY’ OPENING RECEPTION
October 16 | 5-7pm
GRAY Chicago | 2044 W Carroll Avenue
GRAY is pleased to present OH, YOU’VE GOT TO COME BACK TO THE CITY, a solo exhibition by Theaster Gates. The exhibition opens at GRAY Chicago with a public reception for the artist on October 16, and remains on view through December 20, 2025. This is Gates’s fourth solo exhibition with GRAY. In OH, YOU’VE GOT TO COME BACK TO THE CITY, Gates brings together a new series of tar paintings, sculpture, and installation to tell an allegory of the city in decay and the potential contained within its ruins. The exhibition’s title comes from a song by Chicago musician and poet Marvin Tate, in which the City, personified as a character, has cleaned up its act and attempts to lure its residents back from the suburbs.
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AFRORHYTHMIC: A FELABRATION
October 16 | 8pm-1am
Room 43 | 1401 E. 43rd
Soundrotation, in conjunction with Ty Harvey’s Dungeon Series, is back with one of the most anticipated parties of the year, AFRORHYTHMIC: A Felabration. In observation of what would have been the 87th birthday of Nigerian music pioneer and activist Fela Anikulapo Kuti, join DJ Duane Powell as he curates a musical journey centered around Fela’s vast classic catalog and all that it inspired. African rhythms be it Afrobeat, Afro-Cuban, Afro-Brazil, AfroHouse, Gqom, Broken beat etc.
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YOKO ONO: MUSIC OF THE MIND EXHIBITION PREVIEW
October 17 | 7:00 pm – 10:00 pm
Museum of Contemporary Art Chicago | 220 E Chicago Avenue
MCA Members enjoy first-look access to the MCA’s newest exhibitions alongside curators, artists, and fellow art enthusiasts. Pritzker Director Madeleine Grynsztejn and the MCA invite you and a guest to attend the Members’ Preview for Yoko Ono: Music of the Mind. Mingle with fellow MCA Members and enjoy a live DJ set and cash bar, while being among the first to welcome the MCA’s newest exhibition to Chicago.
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19TH ANNUAL MARWEN ART FAIR
October 17 | 6:30-9:30pm
Marwen | 1111 S. Homan Avenue
Art Fair is Marwen’s biggest annual event, transforming 3 floors of our building into a gallery with over 400 unique works by over 150 artists from our expanded community. Enjoy an open bar and heavy appetizers while you bid on artwork by Marwen young artists, Teaching Artists and METAs, staff, and alumni. Tickets are $50 in advance or $60 at the door.
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STEVE AOKI
October 17 | 7PM
TAO Chicago |
Steve Aoki back in Chicago with Nathan Scott.
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WEST LOOP CONTEMPORARY ART FAIR
October 17, 18 & 19 |
Stephen M Bailey Auditorium Plumbers Hall |
A curated boutique expo with over 40 invitation-only fine artists offering direct sales to the public. The Fall West Loop Contemporary Fine Art Expo will feature a Unique Collection of Eclectic, Extraordinary and Diverse Art, and offer the opportunity to meet all the Artists in person.
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MAPPING FROM MEXICO: NEW NARRATIVES FOR THE HISTORY OF CARTOGRAPHY
October 16-18 | 12pm
Soldier Field | 1410 Special Olympics Drive
The 2025 (22nd) Nebenzahl Lectures series continue to promote new thinking in map history by asking how orienting our stories from Mexico, looking out toward the rest of the world, challenges common narratives and popular assumptions in the history of mapmaking. Despite the prominent role mapping in Mexico has played, cartographic histories are often told from a European perspective
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CHICAGO SYMPHONY ORCHESTRA
October 16-19 | 6:30-10:30PM
Symphony Center |
This weekend, lineup of events hosted by the Chicago Symphony Orchestra including: Klaus Mäkelä leads Berlioz’s Symphonie fantastique, signature Fall in Love with Music event, Notes for Peace and SCP Piano with Yunchan Lim.
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LYRIC OPERA OF CHICAGO PRESENTS MEDEA
October 17 | Doors 7PM
Lyric Opera House |
Lyric Opera of Chicago presents Medea, a tale of infidelity and revenge like no other. Euripides’s millennia-old tragedy comes to life — and gruesome death — in this presentation of acclaimed director Sir David McVicar’s iconic, grand-scale production.
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WE LOVE YACHT ROCK
October 18 | 12:00 pm – 6:00 pm
Navy Pier|
Set Sail—Without Leaving Shore! Experience the smooth sounds and effortless cool of the late ’70s and early ’80s at We Love Yacht Rock, a free one-day celebration at Navy Pier.
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BALD BROTHERS: KEVONSTAGE & TONY BAKER
October 18 | 6pm(Doors)
The Chicago Theatre
Bald Brothers: KevOnStage and Tony Baker will bring a freestyle comedy show to Chicago.
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WINES IN THE WILD: SIP & SAFARI
October 9 | 7PM
Brookfield Zoo Chicago | 31st Street and Golfview Avenue, Brookfield
Wines in the Wild features the perfect blend of wildlife and – you guessed it – wine! Join us for a wonderful evening in the newly renovated Discovery Center at Brookfield Zoo Chicago. The evening will include wine/liquor tastings with representatives from wineries and distilleries throughout the United States, delicious food from our catering team, the SSA Group, animal ambassadors, as well as a silent auction with unique travel, wine, and Zoo-centric items! It’s a night you won’t want to miss!
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CHICAGO FIRE FC DECISION DAY GAME WATCH PARTY
October 18 |
Revolution Brewing Chicago |
Join us on Saturday, October 18, at Revolution Brewing (3340 N Kedzie Ave, Chicago, IL) for the ultimate Chicago Fire FC Watch Party! The fun starts at 4 PM, with kickoff at 5 PM as we take on the New England Revolution in a Decision Day matchup that determines our playoff position. We’re also bringing back the fan-favorite Hazy Pitch IPA, brewed in celebration of the Fire. Plus, enjoy exclusive opportunities throughout the event:
Connect with Fire front office executives to discuss 2026 season memberships, Enter raffles for exciting prizes, enjoy a free drink, learn how to enjoy free playoff tickets. Celebrate with fellow fans and enjoy great vibes as we cheer on the Fire.
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BRANDY AND MONICA BOY IS MINE TOUR
October 18 |
United Center |
The highly anticipated The Boy Is Mine Tour is coming to United Center on October 18! The iconic GRAMMY Award-winning artists, Brandy and Monica, will embark on their first-ever co-headlining tour. It also marks a historic moment more than 25 years in the making, building on the legacy of their 1998 game-changing duet “The Boy Is Mine,” which spent a record-shattering 13 consecutive weeks at #1 on the Billboard Hot 100 and became a defining cultural touchstone of late ‘90s R&B.Joining them is a powerhouse lineup of special guests: GRAMMY-winning superstar Kelly Rowland, chart-topping singer-songwriter and GRAMMY winner Muni Long, and rising star Jamal Roberts, fresh off his 2025 American Idol Season 23 win.
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OPEN HOUSE CHICAGO 2025
October 18-19
Chicago
Open House Chicago (OHC), one of the largest architecture and urban exploration festivals in the world, returns to celebrate 15 years of architecture, culture and community.
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CHICAGO ARTISTS COALITION
October 18 | 6-10:30pm
SECRIST | BEACH |
Celebrate 51 years of creativity and connection-building with us in your funkiest 70’s attire. We’ll honor 15-year CAC board member and EXPO founder Tony Karman, enjoy a performance by CAC Alum Celeste, and disco the night away with our outstanding DJ Duane Powell. Bites by All Together Now and beverages included!
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INVICTUS & AN AFRICAN AMERICAN REQUIEM
October 18 | 7:30pm
Harris Theater at Millennium Park | 205 E. Randolph
Ear Taxi Festival, the Chicago Philharmonic, Apollo Chorus of Chicago, and Cedille Records have partnered together for the world premiere of Stacy Garrop’s Invictus and Midwestern premiere of Damien Geter’s powerful An African American Requiem. Nearly 200 musicians take the stage, amplifying voices past and present in a stirring call for justice, resilience, and empathy.
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CHICAGO HUMANITIES FEST UCHICAGO ARTS & HUMANITIES DAY
October 18 | 10am-7:00pm
Harris Theater at Millennium Park | 205 E. Randolph
What makes us human? On October 18, Chicago Humanities and the University of Chicago Arts & Humanities Division join forces to explore this timeless question through a dynamic series of events. For more than four decades, UChicago’s distinguished faculty have hosted an annual Humanities Day each fall — presenting vibrant humanistic research and teaching to a broad audience. Together, we’re expanding this beloved tradition, creating new opportunities to discover how the arts and humanities allow us to understand, individually and collectively, who we’ve been, who we are, and who we might become..
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BOO! BRUNCH
October 19 | 10 a.m. and 12 p.m.
Brookfield Zoo Chicago | 31st Street and Golfview Avenue, Brookfield
Join us for a fun-filled brunch in the Pavilions! Enjoy a live Interactive DJ spinning spooky tunes, capture memories at our spine-tingling photo ops, and enjoy spooky face painting for all kids – included! Every child also receives a free pumpkin to decorate at our festive Pumpkin Painting Station.
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CHICAGO BEARS VS NEW ORLEANS SAINTS
October 19 | 12pm
Soldier Field | 1410 Special Olympics Drive
Coming off a win against the Commanders, the Bears (3-2) face the New Orleans Saints (1-5).
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LINCOLN SQUARE GREEKTOBERFEST
October 18-19 | 1-5PM
St Demetrios Greek Orthodox Church | 2727 W. Winona Street
Lincoln Square GreekToberfest 2025. Authentic Greek Food, Pastries, Loukoumades, Greek Music & Dancing (Dine In or Carry Out)
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*Cover image credit Unsplash
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