Fall events in Wicker Park
37 upcoming. Fall in Wicker Park and Bucktown, Chicago: art walks, festivals, Halloween events and neighborhood happenings.
TodayFriday, October 16
6 to 8pm
Quimby's BookstoreQuimby'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.
7 to 8:15pm, through Oct 18$40
Chopin TheatreChopin 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.
7 to 9:40pm, through Oct 18$40
Chopin TheatreKokandy 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.
7:30 to 9pm
The Den TheatreWorld 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.
10pm$28.84
Empty BottleBoston slowcore trio Horse Jumper of Love plays a late Empty Bottle show with Flooding and Sects. Doors 9pm, show 10pm, 21 plus.
All day, through Oct 24
The Den TheatreA musical comedy from a visiting company with a run at The Den Theatre in Wicker Park.
All day, through Oct 24
The Den TheatreAmy Herzog's acclaimed play about a grandmother and her grandson, staged by a visiting company at The Den Theatre.
All day, through Oct 31
The Den TheatreA comedy show from a visiting company with a run at The Den Theatre in Wicker Park through Halloween night.
TomorrowSaturday, October 17
10am to 2pmFree
ChicagoAnnual 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.
12 to 6pmFree
ChicagoNeighborhood-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.
6:30 to 7:30pm$52
Wicker Park Lutheran ChurchMetallica'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.
8:30 to 9:30pm$61
Wicker Park Lutheran ChurchFever'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.
WednesdayOctober 21
8pm$26.78
Empty BottleWelsh jangle pop band The Tubs plays Empty Bottle with Mopar Stars on its fall tour. An 8pm midweek stop for fans of bright, guitar led indie.
ThursdayOctober 22
7pm
The Den TheatreNew 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.
SundayOctober 25
10am to 4pmFree
ChicagoThe 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.
9pm$20
Empty BottleHalloween 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.
TuesdayOctober 27
6pmFree
Easy BarFree pumpkin carving contest with pre scooped pumpkins and tools provided, prizes for best, most creative and ugliest, presented by New Belgium.
WednesdayOctober 28
7:30pm$30.57
SubterraneanPost hardcore band Wolf & Bear plays upstairs at Subterranean with Coletta and Origami Button. Doors 6:30pm, show 7:30pm, 17 plus.
ThursdayOctober 29
7:15 to 8:45pm$35
The Den TheatreAustralian comic Josh Thomas, creator of Please Like Me, brings his new stand up show Jiggle Jiggle to Wicker Park for one night at The Den Heath Mainstage.
SaturdayOctober 31
3 to 6pmFree
ChicagoNeighborhood 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.
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