Fall events in Wicker Park
Fall in Wicker Park and Bucktown, Chicago: art walks, festivals, Halloween events and neighborhood happenings.
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Friday, October 2 Today
WPB First Fridays Art Walk6 to 8pmFree1389 N Milwaukee Ave, Chicago, IL 60622The Wicker Park Bucktown Chamber of Commerce hosts its free monthly self-guided art walk, with galleries, pop-up spaces and artist studios opening their doors from 6 to 8 pm. This month's edition includes a student series showcasing Pritzker elementary artwork at the Chamber offices, plus beverages and light bites at select stops.
Sunday in the Park with George at Chopin Theatre7 to 9:40pm, day 2 of 3, Oct 1 to 3$401543 W Division St, Chicago, IL 60642Kokandy Productions' revival of Sondheim and Lapine's Pulitzer-winning musical about Georges Seurat, the first Chicago storefront staging in over 15 years. Now extended through Nov 29 after strong reviews from the Tribune, Sun-Times and Reader. Plays the intimate Chopin Studio downstairs, about 2 hours 40 minutes.
Chopin in Winter at Chopin Theatre7 to 8:15pm, day 1 of 3, Oct 2 to 4$401543 W Division St, Chicago, IL 60642Chopin Theatre Productions stages its own production of MacArthur Fellow Stuart Dybek's celebrated Chicago story, set in a postwar working-class neighborhood. Actor Yasen Peyankov plays all the characters while pianist Jana Pavlovska weaves fifteen Chopin pieces and boogie-woogie through the storytelling. Limited engagement, about 75 minutes.
Noel Miller: Special Taping7:15pm1331 N Milwaukee Ave, Chicago, IL 60622Touring comedian Noel Miller (TMG Show, Everything is F#&ked tour) tapes his new comedy special live at The Den Theatre in Wicker Park. Shows October 2 and 3; two-item minimum.
Saturday, October 3 Tomorrow
Candlelight: Queen vs. ABBA8:30 to 9:30pm$681500 N Hoyne Ave, Chicago, IL 60622Candlelight's candlelit string-quartet series takes over the 1906 Romanesque Revival church for a night of Queen and ABBA hits arranged for strings, performed by the Metropolis String Quartet. About 60 minutes, all ages 8 and up.
Saturday, October 10
Eric Oren7pm1331 N Milwaukee Ave, Chicago, IL 60622Chicago comedian and Second City grad Eric Oren records his newest hour of stand-up live at The Den Theatre in Wicker Park. Ages 18 and over.
Candlelight: Neo-Soul Favorites8:30 to 9:30pm$521500 N Hoyne Ave, Chicago, IL 60622The Candlelight series brings neo-soul and hip-hop favorites to Wicker Park Lutheran Church: Prince, Lauryn Hill, SZA, Frank Ocean, D'Angelo, Childish Gambino and more, played by string quartet under a sea of flameless candles. About 65 minutes.
Friday, October 16
Yoko Ono Creation Celebration and FEMME FANTASQUE #2 Release Party6 to 8pm1854 W North Ave, Chicago, IL 60622Quimby's hosts a Yoko Ono birthday celebration paired with the release party and interactive art show for FEMME FANTASQUE #2 with Mike Smith, then an 8 pm musical march from the store to the Six Corners at North and Milwaukee with Environmental Encroachment. Wicker Park's beloved zine shop does this kind of thing better than anyone.
Randomness at a Moment in Time (world premiere)7:30 to 9pm1331 N Milwaukee Ave, Chicago, IL 60622World premiere of an original one-act drama at The Den Theatre: a troubled WWII veteran returns home and criss-crosses the country on one last mission. Ages 16 and up. Plays Oct 16 through 18 in Wicker Park.
Saturday, October 17
Boo-Palooza & BarkPalooza10am to 2pmFree1425 N Damen Ave, Chicago, IL 60622Annual family Halloween party in Wicker Park: kids' musicians, a costume parade and contest, pumpkin patch and decorating, games, and a straw maze, plus BarkPalooza's dog costume parade. Suggested donation of $10 per family. Note: the 2026 event page is not yet published; the time shown is carried from the prior year's listing.
Wicker Park Bucktown Thrift Riot12 to 6pmFree1425 N Damen Ave, Chicago, IL 60622Neighborhood-wide shopping event spanning more than 20 thrift, vintage and resale boutiques along Damen, Division and Milwaukee. Free to browse on your own; a $45 VIP shopping shuttle runs two sessions (noon to 3 and 3 to 6) with drinks, snacks, discounts and a swag bag. Five stores hide specially marked items worth a $50 gift card each.
Candlelight: Tribute to Metallica6:30 to 7:30pm$521500 N Hoyne Ave, Chicago, IL 60622Metallica's catalog gets the candlelit string treatment in the historic Wicker Park church: Enter Sandman, Master of Puppets, Nothing Else Matters and more, performed by the Metropolis String Quartet. 60 minutes, ages 8 and up.
Candlelight: The Best of Hans Zimmer8:30 to 9:30pm$611500 N Hoyne Ave, Chicago, IL 60622Fever's Candlelight series pairs Hans Zimmer's film scores with the glowing sanctuary of Wicker Park Lutheran Church: Interstellar, The Dark Knight, Gladiator, Dune, Inception and more, played by string quartet. About 60 minutes.
Thursday, October 22
Stone and Stone on the Road7pm1331 N Milwaukee Ave, Chicago, IL 60622New York twin comedy duo Stone and Stone (Last Comic Standing, Comedy Central) make their Chicago debut at The Den Theatre in Wicker Park. Two-item minimum.
Sunday, October 25
Meet Me On Milwaukee Series10am to 4pmFreeMilwaukee Ave, Chicago, IL 60622The final car-free Sunday of the season: Milwaukee Avenue closes to traffic from North and Damen to Ashland for a day of walking, biking, sidewalk sales, live music, fitness classes, and pop-up vendors. Presented by the Wicker Park Bucktown Chamber of Commerce. Free.
The Dracula Show Halloween Special9pm$201035 N Western Ave, Chicago, IL 60622Halloween special of the live-audience comedy-variety show hosted by Dracula, with sets from Redder Moon and Corpse Dust plus DJ Scary Lady Sarah. Doors 8pm, show 9pm at the Empty Bottle in Wicker Park. 21 and over.
Saturday, October 31
WPB Trick-or-Treat3 to 6pmFree1414 N Ashland Ave, Chicago, IL 60622Neighborhood trick-or-treating along Wicker Park Bucktown business corridors, organized by the chamber with a digital treat map of participating stops. Costumes encouraged. Check the event page for the map. Free.
The Jazz Room: This is Halloween Edition6 to 7pm$271331 N Milwaukee Ave, Chicago, IL 60622Halloween edition of the 1920s speakeasy-style jazz, soul, and blues show at The Den Theatre in Wicker Park. Shows run about one hour; doors open 30 minutes early. Tickets from $26.80.
Daft Disko Halloween: Chicago9 to 11pm$212011 W North Ave, Chicago, IL 60647French house and disco Halloween party at Subterranean in Wicker Park, presented by ORLOVE. Costumes encouraged. 21 and over. Tickets from $20.98.
Thursday, November 19
The Deep End (world premiere)7:30 to 10pm, day 1 of 4, Nov 19 to 22$121331 N Milwaukee Ave, Chicago, IL 60622New Wave Theatre Company's world premiere of an original play by Z. Croix Kelchen: a woman loses herself in a VR product called The Diving Board and starts questioning what is real. Plays The Den Theatre in Wicker Park, evenings at 7:30 and Sunday matinees at 3.
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