50 Things to Do in Chicago This Weekend October 23 – 25, 2026
Discover the best events and activities happening in Chicago this weekend.
MarketLister's Top 5 Weekend Picks in Chicago
Arts in the Dark Halloween Parade
Chicago’s signature nighttime Halloween parade is the weekend’s strongest public spectacle: a free, all-ages procession of illuminated puppets, costumes, music, dance, and cultural organizations against the Grant Park skyline. It has the broadest crowd appeal and best visual potential of the candidate set. Location: Columbus Drive in Grant Park, Chicago, IL; official Attend/About pages state the parade moves north from Balbo Drive to Monroe Street. Dates: Saturday, October 24, 2026, 6:00 PM – 8:00 PM CT. Admission: Free; No tickets required; free to watch from the sidewalk. Availability: Verified scheduled, free, open to the public, and rain or shine. No tickets required. Note: Muse listed Balbo to Jackson; the most detailed official Attend/About/Participate pages currently state Balbo to Monroe, while the homepage still contains a conflicting Balbo-to-Jackson reference. Reference: https://artsinthedark.com/attend/ Reference: https://artsinthedark.com/about/
Día de los Muertos Xicágo
A major, free, community-rooted Día de los Muertos celebration with ofrendas, live performances, art activities, and an illuminated ofrenda projected onto the museum exterior. It ranks above several ticketed Halloween attractions because it is culturally significant, distinctive to Chicago’s Pilsen community, highly visual, and broadly accessible. Location: National Museum of Mexican Art / Harrison Park, 1852 W 19th Street, Chicago, IL 60608. Dates: Saturday, October 24, 2026, 3:00 PM – 8:00 PM CT. Admission: Free (museum admission always free); No tickets required. Availability: Verified scheduled, free, open to the public, and rain or shine. No tickets required. Reference: https://nationalmuseumofmexicanart.org/events/dia-de-los-muertos-xicago-2026
Night of 1,000 Jack-o'-Lanterns
A large, polished nighttime pumpkin-art trail with artist-carved pumpkins, giant pumpkins, live carving, costumed performers, seasonal food and drink, and a new illuminated sculpture. Although outside city limits, it fits the geography rule as a major Chicago-area cultural attraction reasonably accessible to local residents. Location: Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe, IL 60022. Dates: Research-period nights: Friday, October 23 – Sunday, October 25, 2026; event run October 7–11, 14–18, and 21–25, 2026; 6:30 PM – 10:30 PM CT, with ticketing page listing last ticketed entry at 9:30 PM. Admission: From $24 adult, $17 child ages 3-12 (nonmember, advance); members from $20; Timed-entry tickets required; purchase online in advance. Availability: Verified scheduled and ticketed. Advance timed-entry tickets are offered through the official Chicago Botanic Garden ticketing page. Muse’s listed last entry of 10:00 PM was corrected to the ticketing page’s 9:30 PM last ticketed entry. Reference: https://www.chicagobotanic.org/halloween Reference: https://secure.chicagobotanic.org/WebStore/shop/ViewItems.aspx?c=22120&cg=2050
62nd Chicago International Film Festival
The closing weekend of North America’s longest-running competitive film festival brings international and independent cinema, special programs, attending artists, and festival-scale cultural energy across Chicago. It is less visually immediate than the top three picks but has major local significance and strong arts appeal. Location: Multiple Chicago venues, including AMC NEWCITY 14, Music Box Theatre, Gene Siskel Film Center, Reva and David Logan Center for the Arts, and others. Dates: Festival runs October 14–25, 2026; closing-weekend screenings and events occur Friday, October 23 – Sunday, October 25, 2026, at varying times by schedule. Admission: General tickets from $22; passes from $200 (members) / $240 (non-members); Tickets required; available online and at festival box offices. Availability: Verified scheduled. Tickets and passes are sold through the official festival site; availability varies by individual screening, and some screenings may become standby-only. Reference: https://www.chicagofilmfestival.com/festival/ Reference: https://www.chicagofilmfestival.com/festival/tickets/ Reference: https://www.chicagofilmfestival.com/about/venues/
AirOtic BITE! / BITE! – Halloween Circus Experience Chicago
The strongest adults-only pick: a Halloween-season circus and cabaret experience with aerial acts, burlesque, theatrical staging, cocktails, and a dark immersive atmosphere. It adds category diversity and a distinctive 21+ nightlife option that is more unique than another pumpkin patch or haunted house. Location: Experience 868, 868 N Franklin Street, Chicago, IL 60610. Dates: Friday, October 23 – Sunday, October 25, 2026, within the October 9 – November 1, 2026 Chicago run; standard schedule listed as doors 6:00 PM, show 7:00 PM – 8:00 PM CT. Admission: Standard $71; Preferred $107; VIP $114; Super VIP $135; Advance online ticket purchase required (Eventbrite/Fever). Availability: Verified scheduled and ticketed. Fever listed the experience as open with 'Tickets Selling Fast' and 'Low availability'; standard and preferred ticket tiers were visible, while VIP and Super VIP were shown as sold out in the visible selector state. Guests must be 21+ with valid ID. Reference: https://feverup.com/m/736266?seasonal=pc4a1bp Reference: https://airoticcirquesoiree.com/chicago/
More Things to Do in Chicago This Weekend
Showing 45 events
13th Floor Haunted House
USA Today-ranked haunted house in a 40,000-sq-ft Schiller Park warehouse with two 2026 haunts: Black Hollow Institute and The Woman in White. Location: 13th Floor Haunted House, 5050 River Road, Schiller Park, IL 60176. Dates: October 23-25, 2026 (select nights; season runs September 12 - November 8, 2026); Friday 7:30 PM - 10:00 PM; Saturday 7:00 PM - 10:00 PM; Sunday 7:00 PM - 9:30 PM. Admission: Tickets from $24.99; Tickets online only; timed entry. Availability: Verified scheduled and ticketed for the research weekend; tickets sold online only Reference: https://13thfloorchicago.com/
Jack's Pumpkin Pop-Up
Chicago's biggest pumpkin patch pop-up on Goose Island: 10,000+ pumpkins, downtown corn maze, carnival games, axe throwing, and fall cocktails. Location: Jack's Pumpkin Pop-Up, Goose Island, 1265 W Le Moyne Street, Chicago, IL 60642. Dates: October 23-25, 2026 (event runs September 19 - November 1, 2026); Friday 4:00 PM - 11:00 PM; Saturday 12:00 PM - 11:00 PM; Sunday 12:00 PM - 10:00 PM. Admission: Timed tickets from $25; Timed-entry tickets required; purchase online in advance. Availability: Verified scheduled; timed-entry tickets on sale Reference: https://www.jackspumpkinpopup.com/
Boo! at the Zoo
Brookfield Zoo's month-long Halloween celebration wraps up Oct 23-25: trick-or-treating, costume parades, pumpkin animal enrichment, and festive photo ops. Location: Brookfield Zoo Chicago, 3300 Golf Road, Brookfield, IL 60513. Dates: October 23-25, 2026 (event runs October 3-25, 2026); Zoo hours 10:00 AM - 5:00 PM; trick-or-treating 11:00 AM - 5:00 PM weekends; costume parades 12:00 PM and 3:00 PM weekends. Admission: Free with zoo admission; Zoo admission required; no separate event ticket. Availability: Verified scheduled; included with daily admission, no separate ticket needed Reference: https://brookfieldzoo.org/stories/10-things-to-do-at-boo-at-the-zoo
Chase Park After Dark Haunted House
Annual charity haunted house in Chase Park's old theater, this year themed 'Chuckles' Sweet 16... A Party to Die For.' Location: Chase Park, 4701 N Ashland Ave, Chicago, IL 60640. Dates: October 23-25, 2026; Friday & Saturday 7:00 PM - 10:00 PM; Sunday 6:00 PM - 9:00 PM. Admission: $16 per ticket; Advance online ticket purchase required; no door sales. Availability: Tickets $16, must be purchased online in advance; no ticket sales at the door. Proceeds support Chase Park's after-school teen program. Reference: https://www.chicagoparkdistrict.com/events/park-after-dark-chase-13
Omar
Lyric Opera's company premiere of the Pulitzer Prize-winning opera by Rhiannon Giddens and Michael Abels, a Lyric co-commission telling Omar ibn Said's story of survival, faith and identity. Location: Lyric Opera House, 20 N Upper Wacker Dr, Chicago, IL 60606. Dates: October 23, 25 and 28, 2026 (in-window: Oct 23 & 25); Friday, October 23, 7:00 PM; Sunday, October 25, 2:00 PM. Admission: From $98 (Oct 23); from $123 (Oct 25 matinee); Tickets required; available via lyricopera.org or 312.827.5600. Availability: Tickets on sale via lyricopera.org; Friday 10/23 from $98, Sunday 10/25 matinee from $123. No sellout reported. Reference: https://www.lyricopera.org/shows/upcoming/2026-27/Omar/
Mary Cassatt: After Impressionism
The Art Institute of Chicago's first Cassatt exhibition in 25+ years, marking the centennial of her death with 75+ paintings, pastels and prints from her experimental post-Impressionist years. Location: The Art Institute of Chicago, 111 S Michigan Ave, Chicago, IL 60603. Dates: September 6, 2026 - January 3, 2027 (open during Oct 23-25); Museum hours: Fri & Sun 11 AM-5 PM; Sat 11 AM-5 PM. Admission: General admission (adults $32) + $7 exhibition ticket; members free; Exhibition ticket required ($7) in addition to general admission. Availability: On view; no closure reported. Note: museum closed Tuesdays. Note: artic.edu bot-gates automated fetches (403); page confirmed live via official indexed page. Reference: https://www.artic.edu/exhibitions/10487/mary-cassatt-after-impressionism
Topdog/Underdog
Steppenwolf's production of Suzan-Lori Parks' Pulitzer-winning drama, directed by Tony winner Kenny Leon and starring ensemble members Glenn Davis and Namir Smallwood. Location: Steppenwolf Theatre Company, Downstairs Theater, 1650 N Halsted St, Chicago, IL 60614. Dates: Through November 1, 2026 (performances during Oct 23-25); See steppenwolf.org for performance calendar. Admission: Not confirmed; see steppenwolf.org; Tickets required; available via steppenwolf.org. Availability: Tickets on sale via steppenwolf.org; no sellout reported. Reference: https://www.steppenwolf.org/whats-on
Lee Miller: Fearless
First comprehensive survey in 25+ years of photographer Lee Miller's work — ~150 works tracing her path from fashion model to Surrealist to Vogue war correspondent. Location: The Art Institute of Chicago, 111 S Michigan Ave, Chicago, IL 60603. Dates: August 29 - December 7, 2026 (open during Oct 23-25); Museum hours: Fri & Sun 11 AM-5 PM; Sat 11 AM-5 PM. Admission: General admission (adults $32); members free; General admission; no separate ticket indicated. Availability: On view; no closure reported. Note: museum closed Tuesdays. Note: artic.edu bot-gates automated fetches (403); page confirmed live via official indexed page. Reference: https://www.artic.edu/press/press-releases/422/lee-miller-fearless
Edward Scissorhands in Concert
The Chicago Philharmonic performs Danny Elfman's iconic Edward Scissorhands score live to picture at the Auditorium Theatre, with a Svengoolie-hosted Halloween pre-party. Location: Auditorium Theatre, 50 E Ida B. Wells Drive, Chicago, IL 60605. Dates: Saturday, October 24, 2026; 7:30 PM; VIP pre-party 5:30 PM - 7:15 PM. Admission: From ~$69; VIP Do312 pre-party $50 extra; Advance ticket purchase recommended. Availability: Tickets on sale via AXS/authorized ticketing; no sellout or cancellation notice found. Reference: https://chicagophilharmonic.org/events/edward-scissorhands/
CircuitMOM & Uncle Present: Haunted Hollywood
CircuitMOM Productions' signature Halloween event turns House of Blues into a theatrical dance spectacle with elaborate decor, lighting, projections, synchronized dancers, and driving house and circuit beats. Location: House of Blues Chicago, 329 N Dearborn St, Chicago, IL 60654. Dates: Saturday, October 24, 2026; 9:00 PM (doors); performance begins 9:00 PM. Admission: From ~$86; Advance ticket purchase required; 21+ only. Availability: Tickets on sale via Ticketmaster/authorized ticketing; no sellout or cancellation notice found. Reference: https://www.choosechicago.com/event/circuitmom-uncle-present-haunted-hollywood/
Thee Phantom and The Illharmonic Orchestra
Hip-hop maestro Thee Phantom and vocalist The Phoenix blend raw lyricism and DJ turntablism with a live orchestra of strings, horns, woodwinds, and piano at the Riviera. Location: Riviera Theatre, 4746 N Racine Ave, Chicago, IL 60640. Dates: Saturday, October 24, 2026; 7:30 PM (doors 6:00 PM). Admission: From ~$63; Advance ticket purchase recommended. Availability: Tickets on sale via AXS/authorized ticketing; no sellout or cancellation notice found. Reference: https://www.choosechicago.com/event/thee-phantom-and-the-illharmonic-orchestra-2/
Brett Goldstein: Sex, Death & Small Talk Tour
Ted Lasso star and two-time Emmy winner Brett Goldstein brings his stand-up tour to the Chicago Theatre for two Sunday shows. Location: The Chicago Theatre, 175 N State St, Chicago, IL 60601. Dates: Sunday, October 25, 2026; 4:00 PM and 7:00 PM. Admission: From ~$80; Advance ticket purchase recommended. Availability: Tickets on sale; no sellout or cancellation notice found for the Oct 25 shows. Reference: https://www.brettgoldstein.org/tour
Best of The Second City
Chicago's legendary comedy institution presents a fast-moving showcase of classic sketches, songs, and fresh improv from its celebrated ensemble at UP Comedy Club. Location: UP Comedy Club at Second City, 230 W North Ave, Chicago, IL 60614. Dates: Saturday, October 24, 2026; 3:00 PM and 8:00 PM shows. Admission: From ~$65; Advance ticket purchase recommended. Availability: Tickets on sale via Second City box office and authorized ticketing; no sellout or cancellation notice found for Oct 24 shows. Reference: https://www.vividseats.com/best-of-the-second-city-tickets--theater-comedy/performer/54952
Oktoberfest Chicago
Chicago's largest Oktoberfest takes over Fulton Market with official Hofbrau Munchen beer, Bavarian food, live German music, carnival games and stein-holding contests. Location: Fulton Market, Fulton Market, Chicago, IL. Dates: September 17 - October 31, 2026 (open during the research weekend); See official site for daily hours. Admission: Ticketed; see official site for pricing; Tickets via official site. Availability: Verified scheduled; ticketed event, see official site for availability. Reference: https://www.oktoberfestnation.com/
Forest Park Casket Races
The 14th annual casket races: costumed teams push homemade coffin-carts down Beloit Avenue, with a kids-and-pets costume parade and trick-or-treating after. Location: Beloit Avenue between Madison and Adams Streets, 7500 Madison St (Beloit Ave between Madison & Adams), Forest Park, IL 60301. Dates: Saturday, October 24, 2026; 9:30 AM - 12:30 PM CT (racing starts 11:00 AM; casket parade 10:30 AM). Admission: Free to watch; $40 per team to race; No tickets required to watch; team registration via Forest Park Chamber of Commerce. Availability: Verified scheduled; free to watch. Reference: https://Mommypoppins.com/chicago-kids/event/events/forest-park-casket-races
Pretty Good Fest 2026
Free one-day comics and small press festival bringing 100+ cartoonists, publishers, book artists, and zine-makers to the Chicago Athletic Association. Location: Chicago Athletic Association Hotel, 12 S Michigan Ave, Chicago, IL 60603. Dates: Saturday, October 24, 2026; 11:00 AM - 6:00 PM. Admission: Free; No tickets required; free and open to the public. Availability: Free and open to the public; no tickets required. Reference: https://www.prettygoodfest.com
Zoo Brews: Howls and Growls
Adults-only Halloween night at the zoo: trick-or-treat for craft beer and cider across themed areas, with roaming entertainers, DJs, pumpkin carving, and a costume contest. Location: Lincoln Park Zoo, 2001 N Clark St, Chicago, IL 60614. Dates: October 23–24, 2026; 6:30–10:00 PM. Admission: $55–$70 (tiered; members from $44); Advance online ticket purchase required. Availability: Tickets on sale; tiered pricing increases closer to the event Reference: https://www.lpzoo.org/event/zoo-brews-howls-and-growls/
City Cruises Chicago Seadog Haunted River Tour
Haunted-history sightseeing cruise on the Chicago River aboard the Seadog speedboat, timed for Halloween season. Location: City Cruises Chicago – Navy Pier, 600 E Grand Ave, Chicago, IL 60611. Dates: October 23–25, 2026; Departures between 3:00 PM and 7:00 PM. Admission: $37–$60; Advance online booking recommended. Availability: Tickets on sale; no sold-out notice found Reference: https://www.choosechicago.com/event/series/city-cruises-chicago-seadog-haunted-river-tour/?eventDisplay=default
Monstrosity: A Halloween Experience at Colvin House
Immersive theatrical horror night inside a historic Edgewater mansion transformed into Dr. Frankenstein's laboratory, with actors, curated decor, appetizers, and a dance floor. Location: Colvin House, 5940 N Sheridan Rd, Chicago, IL 60640. Dates: Saturday, October 24, 2026; 8:00 PM. Admission: $61.82, includes two drink tickets; Advance online ticket purchase required. Availability: Tickets on sale; no sold-out notice found Reference: https://chicago.citycast.fm/keep-it-local/open-house-chicago-spotlight-get-witchy-at-the-colvin-house
The Jury Experience – Frankenstein on Trial: The Man Who Defied God
Immersive courtroom drama where the audience is sworn in as jurors to decide Victor Frankenstein's guilt, staged at the Museum of Contemporary Art. Location: Edlis Neeson Theater, Museum of Contemporary Art Chicago, 220 E Chicago Ave, Chicago, IL 60611. Dates: Sunday, October 25, 2026; 4:30 PM and 7:00 PM (60 minutes). Admission: From $39; Advance purchase via Fever app/website; no refunds, exchanges permitted up to 48 hours before. Availability: Tickets on sale; no sold-out notice found Reference: https://feverup.com/m/618546/en
Great Food Expo
Two-day culinary expo at the Donald E. Stephens Convention Center with hundreds of food and beverage brands, tastings, cooking demos, and kitchenware vendors. Location: Donald E. Stephens Convention Center, 5555 N River Rd, Rosemont, IL 60018. Dates: Saturday, October 24 - Sunday, October 25, 2026; Saturday 10:00 AM - 5:00 PM; Sunday 11:00 AM - 5:00 PM. Admission: From $6.24; Ticket purchase required; available online. Availability: Tickets on sale from $6.24; no sellout or cancellation found Reference: https://greatfoodexpo.com/chicago/
La Fête du Champagne Chicago 2026
The world's premier Champagne festival returns to Chicago with producer dinners, a masterclass, Franks & Fizz party, Grand Tasting, and Gala Dinner. Location: Avec River North (Grand Tasting & Gala Dinner), Avec River North (per official program; individual event locations vary). Dates: Thursday, October 22 - Saturday, October 24, 2026; Saturday, October 24: Grand Tasting and Gala Dinner (see official program for times). Admission: From $104.98; Ticket purchase required via Eventbrite; 21+ with valid ID. Availability: Tickets on sale $104.98-$1823.25; no sellout notice found Reference: https://www.eventbrite.com/e/la-fete-du-champagne-chicago-2026-tickets-1991730908764
The Oakville Grand Paso Robles Wine Tasting
Inaugural grand tasting with 40 Paso Robles wineries on the 17th floor of 167 Green, with skyline views, chef-paired bites, and an optional master class. Location: The Oakville, 167 N Green St, Floor 17, Chicago, IL 60607. Dates: Sunday, October 25, 2026; 12:00 PM - 3:00 PM (Master Class 11:00 AM - 12:00 PM). Admission: $102 per ticket; Ticket purchase required via Tock; 21+. Availability: Tickets on sale at $102; no sellout notice found Reference: https://www.exploretock.com/the-oakville-chicago/event/617531
Sip & Savor: Sicilian Cheese and Wine Getaway
Guided tasting at Eataly Chicago pairing distinctive Sicilian wines with artisanal cheeses, led by Eataly's beverage experts and cheesemongers. Location: Eataly Chicago, 43 E Ohio St, Chicago, IL 60611. Dates: Friday, October 23, 2026; Not confirmed (evening class; see Eataly listing). Admission: $79.39; Ticket purchase required; 21+ with valid ID; seating first-come, first-served. Availability: Tickets on sale at $79.39; no sellout notice found Reference: https://happeningnext.com/event/sip-andamp-savor-sicilian-cheese-and-wine-getaway-eid1ef0l5rmr8ha
Sip & Savor: Fall Wine & Cheese
Eataly Chicago's lunchtime tasting class pairing fall wines and Italian cheeses with guidance from resident beverage experts and cheesemongers. Location: Eataly Chicago, 43 E Ohio St, Chicago, IL 60611. Dates: Saturday, October 24, 2026; 12:00 PM - 1:00 PM. Admission: From $86.77; Ticket purchase required; 21+ with valid ID; seating first-come, first-served. Availability: Tickets from $86.77; no sellout notice found Reference: https://www.localwineevents.com/view/event/sip-savor-fall-wine-cheese/1036767
Fall Fest at Lincoln Park Zoo
Free harvest festival at Lincoln Park Zoo with pumpkin patch, pumpkin carvers, carnival rides, live music and fall treats alongside the animals. Location: Lincoln Park Zoo, 2001 N Clark St, Chicago, IL 60614. Dates: Fridays-Sundays, September 25 - November 1, 2026 (in window: Friday, October 23 - Sunday, October 25); 10:00 AM - 5:00 PM. Admission: Free admission; rides and select attractions ticketed; No ticket required for admission; ride/attraction tickets sold on site. Availability: Scheduled Fridays-Sundays September 25 - November 1, 2026, including Oct 23-25. Free admission; no sellout found. Reference: https://www.choosechicago.com/event/series/fall-fest-at-lincoln-park-zoo/
Gompers Park Ghoulfest
Second-annual free neighborhood Halloween festival with kids costume parade, trunk-or-treating, pumpkin decorating, fire truck visit and the Jesse White Tumblers. Location: Gompers Park, 5060 N Pulaski Rd, Chicago, IL 60630. Dates: Saturday, October 24, 2026; 2:00 PM - 5:00 PM. Admission: Free; free treat bags included; No ticket required. Availability: Verified scheduled for Saturday, October 24, 2026. Free; no sellout found. Reference: https://www.choosechicago.com/event/gompers-park-ghoulfest/
Slightly Spooky October at Navy Pier
Free family Halloween day at Navy Pier with Mad Scientist Lab experiments, Frankenstein toy making, superhero meet-and-greets and movies in Crystal Gardens. Location: Navy Pier, 600 E Grand Ave, Chicago, IL 60611. Dates: Saturday, October 24, 2026; 1:00 PM - 5:00 PM (family activities); movies in Crystal Gardens from 5:30 PM. Admission: Free; No ticket required. Availability: Verified scheduled for Saturday, October 24, 2026. Free; no sellout found. Reference: https://navypier.org/pier-events/slightly-spooky-october/
BOO-seum Bash
Halloween morning at the Peggy Notebaert Nature Museum: animal encounters, owl pellet dissection, bug explorations, crafts and the butterfly haven, costumes encouraged. Location: Peggy Notebaert Nature Museum, 2430 N Cannon Dr, Chicago, IL 60614. Dates: Sunday, October 25, 2026; 10:00 AM - 1:00 PM (members early entry 9:00 AM). Admission: Ticketed event; general museum admission applies (see naturemuseum.org for current pricing); members enjoy discounted admission and 9:00 AM early entry; Event ticket/museum admission required. Availability: Verified scheduled for Sunday, October 25, 2026, 10:00 AM - 1:00 PM (members early entry 9:00 AM). Ticketed; no sellout found. Reference: https://naturemuseum.org/events/booseum-bash-3
Boo! At The Park
West Edgewater Area Residents' free family Halloween bash at Park 599 with pumpkin decorating, bounce house, circus demos, games, and a live DJ. Location: Park 599, 1623 W Edgewater Ave, Chicago, IL 60660. Dates: Sunday, October 25, 2026; 2:00 PM - 5:00 PM. Admission: Free; No tickets or reservation required; free and open to all. Availability: Free; no RSVP required per 48th Ward fall events listing. Reference: https://andersonville.org/events/aville-o-ween/?mc_cid=f2f72f620d&mc_eid=ef72c3866a
Will Run for Beer Chicago 5K
Scenic lakefront 5K through Lincoln Park followed by the Lager Than Life Brewfest with craft beer samples, food, live music and Oktoberfest energy. Location: Lincoln Park lakefront, Lincoln Park lakefront, Chicago, IL. Dates: Saturday, October 24, 2026. Admission: Not confirmed; Advance registration required via official site. Availability: Registration open per official FAQ; price increases scheduled 9/6/2026 and 10/11/2026. No sellout notice found. Reference: https://willrunforbeerchicago.com/
Morton Arboretum Fall Color 5K
Shotgun-start 5K through the Morton Arboretum at peak fall color, with post-race party, live music, food and a complimentary beer. Location: The Morton Arboretum, 4100 IL Rt. 53, Lisle, IL 60532. Dates: Saturday, October 24, 2026; 8:00 AM shotgun start (cross by 8:15 AM for own pace). Admission: Not confirmed; Advance registration required. Availability: Registration open via BikeSignup/RunSignup; on-site race Oct 24. No sellout notice found. Reference: https://www.bikesignup.com/Race/Info/IL/Lisle/FallColorRunWalk
OUTLAST Chicago
Six-hour trail endurance challenge: run a 5K every hour on the hour across rugged trail terrain — miss a lap and you're out. Location: Trail venue, Palatine, 1599 Pepper Tree Dr, Palatine, IL 60067. Dates: Saturday, October 24, 2026; 8:00 AM start; 6-hour event (laps on the hour). Admission: Not confirmed; Advance registration required. Availability: Registration open on RunSignup for Oct 24, 2026. No sellout notice found. Reference: https://runsignup.com/Race/IL/Palatine/OUTLASTCHICAGO
Haunted Halloween Half Marathon & 5K
Costumed half marathon and 5K through Lincoln Park and along the Lakefront Trail, with a pre-race costume contest offering cash prizes. Location: Lincoln Park / Chicago Lakefront Trail, Lincoln Park / Lakefront Trail, Chicago, IL. Dates: Sunday, October 25, 2026; 8:00 AM race start (costume contest judging 7:15 AM; listing also shows 8:30 AM). Admission: $49; Advance registration required. Availability: Registration open; capped at 500 finishers. No sellout notice found. Reference: https://www.halfmarathons.net/races/haunted-halloween-half-marathon-5k/
Howl-o-ween 5K at Dan Ryan Woods
Halloween-themed 5K (run or walk, dogs welcome) through Dan Ryan Woods forest preserve, raising funds for K9s for Veterans. Location: Dan Ryan Woods - Central Picnic Grove, 2231 W 83rd St, Chicago, IL 60620. Dates: Sunday, October 25, 2026; 9:00 AM. Admission: Not confirmed; Advance registration required (dogs participate free). Availability: Registration open on RunSignup. No sellout notice found. Reference: https://runscore.runsignup.com/Race/Info/IL/Chicago/Howloween5kMidlothianReservoir
Chicago Fall Market for Makers
Two-day fall makers market with 90+ independent makers selling handmade jewelry, apparel, home decor, art and food across two floors, plus DIY stations and photo walls. Location: Artifact Events, 4325 N Ravenswood Ave, Chicago, IL 60613. Dates: October 24-25, 2026; 11:00 AM - 5:00 PM both days. Admission: $6-$12 general admission (varies by day/arrival time); $20 VIP all-weekend; kids under 12 free; Advance tickets recommended; tickets sold online via official ticketing page. Availability: Tickets on sale; no sellout notice found Reference: https://tickets.marketsformakers.com/2026-19-chicago-fall-market-for-makers/
DAY OF THE DEAD MARKET
Second annual Day of the Dead market with handmade Catrinas, papel picado, marigolds, altars, skull planters, jewelry and pan de muerto from local vendors, plus food and a raffle. Location: DAY OF THE DEAD MARKET, 2102 W Cermak Rd, Chicago, IL 60609. Dates: October 24-25, 2026; 12:00 PM - 6:00 PM both days. Admission: Free entry; Free entry; no tickets required. Availability: Scheduled; no cancellation found Reference: https://www.eventbrite.com/e/day-of-the-dead-market-tickets-1999798277481
Manhattan Vintage | Chicago Edition
First-ever Chicago edition of NYC's iconic Manhattan Vintage show: 50+ dealers from across the country with rare archives to everyday vintage across all eras, plus DJ, portraits and full bar. Location: Morgan MFG, 401 N Morgan St, Suite 100, Chicago, IL 60642. Dates: October 24-25, 2026; Saturday: preview 12:00 PM, general admission 1:30-6:00 PM; Sunday: 11:00 AM - 5:00 PM. Admission: $25 1-day general admission; $20 student; $40 preview pass; $65 buddy pass (3 tickets); Tickets via Eventbrite; advance purchase recommended (peak hours may mean waits). Availability: Tickets on sale via Eventbrite; no sellout notice found Reference: https://www.eventbrite.com/e/manhattan-vintage-chicago-edition-october-24-25-tickets-2000994031012?aff=ebdssbdestsearch
Lanterns and Legends: Autumn AAPI Market
Free lantern-lit evening market celebrating Asian folklore and mythology with local AAPI artists, makers and food vendors, plus a stamp rally and costume encouragement. Location: Uni Uni Boba Uptown, 1130 W Argyle St, Chicago, IL 60640. Dates: Sunday, October 25, 2026; 3:00 PM - 8:00 PM. Admission: Free admission; No tickets required; stamp rally participation while supplies last. Availability: Scheduled; no cancellation found Reference: https://www.choosechicago.com/event/lanterns-and-legends-autumn-aapi-market/
Dead City Oddities Market
One-day curated oddities market with 40+ Chicago and Midwest vendors selling dark art, taxidermy, antiques, gothic decor, jewelry and alternative fashion. Location: Epiphany Center for the Arts - Epiphany Hall, 201 S Ashland Ave, Chicago, IL 60607. Dates: Saturday, October 24, 2026; 12:00 PM - 8:00 PM. Admission: $8 general admission (+fees); children 12 and under free; Tickets via DICE; credit card only at the door. Availability: Tickets in stock on DICE; no sellout notice found Reference: https://dice.fm/event/6dope2-dead-city-oddities-market-24th-oct-epiphany-center-for-the-arts-epiphany-hall-chicago-tickets
Meet Me on Milwaukee
Car-free Sunday on Milwaukee Avenue: the street closes to traffic for walking, biking, live music, sidewalk sales, outdoor dining, and neighborhood pop-ups. Location: Milwaukee Avenue, North/Damen to Ashland, Milwaukee Avenue between North/Damen and Ashland, Chicago, IL 60622. Dates: Sunday, October 25, 2026; 10:00 AM - 4:00 PM. Admission: Free; No tickets or registration required; free and open to all. Availability: Verified scheduled; free, no registration required Reference: https://www.optionpremier.com/blogs/milwaukee-avenue-car-free-sundays-2026
Lincoln Park Spooktacular
Two-day free neighborhood trick-or-treat weekend: Saturday along Lincoln Avenue, Sunday along Clark Street and Diversey, with roaming magicians, stilt walkers, and a costume contest. Location: Lincoln Avenue (Saturday) and Clark Street / Diversey Parkway (Sunday), Lincoln Avenue (Diversey to Webster) and Clark Street (Armitage to Diversey), Chicago, IL 60614. Dates: Saturday, October 24 and Sunday, October 25, 2026; 1:00 PM - 4:00 PM each day. Admission: Free; No tickets required; free and open to the public. Availability: Verified scheduled; free neighborhood trick-or-treating, no tickets required Reference: https://mommypoppins.com/chicago-kids/halloween/lincoln-park-chicago-spooky-itinerary-halloween
Pumpkin Party at Gallagher Way
Free family fall party outside Wrigley Field with pumpkin hunting, live music, arts and crafts, costumes, and trick-or-treating. Location: Gallagher Way, 3637 N. Clark St., Chicago, IL 60613. Dates: Saturday, October 24, 2026; 1:00 PM - 5:00 PM. Admission: Free; No tickets required; free and open to the public. Availability: Scheduled; free community event Reference: https://www.thesavvyglobetrotter.com/things-to-do-next-weekend-chicago/
Cemetery Group Ride
Free community bike ride through three of Chicago's north side cemeteries, rolling out from a local bike shop; costumes encouraged. Location: Igor Does My Bike, 5454 N Broadway, Chicago, IL 60640. Dates: Sunday, October 25, 2026; 1:00 PM meet, 1:30 PM rollout. Admission: Free; No tickets or RSVP required. Availability: Free; no RSVP required; costumes welcome. 2nd annual edition. Reference: https://www.edgewaterobserver.com/p/week-of-october-19-25
Spooky Saturday on the Main-Dempster Mile
Evanston's free Main-Dempster Mile Halloween day: trick-or-treating at local businesses, pumpkin carving contest, kids costume parade, and pet parade. Location: Main-Dempster Mile business district, 500 block of Dempster St, Evanston, IL 60201. Dates: Saturday, October 24, 2026; From 11:00 AM (trick-or-treating); kids costume parade 12:00 PM; pet parade 12:30 PM. Admission: Free; No tickets required; free and open to all. Availability: Free; no tickets required. Reference: https://www.jackiemack.com/2026/10/welcome-to-halloweenston-experience-the-many-ways-to-have-a-uniquely-heavanston-halloween-in-26/
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