What’s on in Chicago this October
Every listing for October 2026, in date order
17 listings this October
All monthFridays to Sundays through Nov. 1
Fall Fest at Lincoln Park Zoo
Lincoln Park Zoo, 2001 N. Clark St., Lincoln Park
Free admission every Friday through Sunday: s’mores, professional pumpkin carvers, live music and a pumpkin patch. The Ferris wheel and other rides cost extra.
All monthThrough Nov. 1
Jack’s Pumpkin Pop-Up
1265 W. Le Moyne St., Goose Island
A big Halloween pop-up with a giant corn maze, carnival games, axe throwing, bars and food trucks.
All monthThrough Nov. 29
Where Memory Lives: 40 Years of Día de Muertos
National Museum of Mexican Art, 1852 W. 19th St., Pilsen
The museum’s 40th annual Day of the Dead exhibition looks back through its own collection at how the holiday, and the museum, have changed over four decades.
TheaterThrough Oct. 11
Chicago International Latino Theater Festival
Theaters citywide
The last days of a month-long showcase of new work and rising talent from Chicago’s Latino theater community.
HalloweenOct. 7–11, 14–18 and 21–25, 6:30 to 10:30 p.m.
Night of 1,000 Jack-o’-Lanterns
Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe
More than 1,000 real pumpkins carved by artists line a paved path, including about 75 giants of up to 150 pounds. Buy tickets ahead, because you can’t just show up.
FashionOct. 8 to 18
Chicago Fashion Week
Venues citywide
More than 50 events and runway shows built around Chicago’s own design community.
Food and drinkOct. 9 to 11
Lincoln Park Wine Festival
Lincoln Park
An outdoor market with wine tastings, sommeliers on hand and live performances.
HistoryOct. 10 and 11
Historic Pullman House Tour
Historic Pullman, Far South Side
A rare chance to step inside Pullman’s mansions and workers’ cottages, a neighborhood tradition for more than 50 years.
SportsSunday, Oct. 11, from 7:20 a.m.
Chicago Marathon
Downtown and 26.2 miles of neighborhoods
Cheering from the sidewalk is free. If you’re visiting that weekend, plan around the course, because streets along the route close on race morning.
FilmOct. 14 to 25
Chicago International Film Festival
Theaters citywide
The 62nd edition of the longest-running competitive film festival in North America, with features, documentaries and shorts from around the world.
ArchitectureOct. 17 and 18
Open House Chicago
More than 200 sites in 30-plus neighborhoods
Free, behind-the-scenes access to buildings that are usually closed to the public. Hours vary by site, and some open only one day.
HalloweenSaturday, Oct. 17
Spooky Zoo
Lincoln Park Zoo, Lincoln Park
Free trick-or-treating for all ages, with a scavenger hunt, kid-friendly entertainment and free carousel rides on top of the usual Fall Fest fun.
Food and drinkOct. 23 and 24
Zoo Brews: Howls and Growls
Lincoln Park Zoo, Lincoln Park
A craft beer and cider festival at the zoo, timed for Halloween, so wear the costume.
HalloweenSaturday, Oct. 24, evening
Arts in the Dark Halloween Parade
State Street, The Loop
An evening parade of giant puppets, lanterns, floats and performers that treats Halloween as the artists’ holiday. Free to watch; this year’s start time hasn’t been posted yet.
MusicSaturday, Oct. 24, 6 to 10 p.m.
Chicago Made Music Showcase Finale
Chicago Cultural Center, 78 E. Washington St., The Loop
Local musicians perform for a live audience and a panel of industry pros, with a career-changing grand prize on the line.
HalloweenSaturday, Oct. 31, fest from 11 a.m., parade 6:30 p.m.
Haunted Halsted Halloween Parade and Fest
Halsted Street from Aldine to Addison, Northalsted
For the parade’s 30th year it’s an all-day, all-ages street fest with food, music and local vendors, leading into the city’s only Halloween-night parade.
HalloweenSaturday, Oct. 31, evening
Haunted Halloween Ball
Congress Plaza Hotel, 520 S. Michigan Ave., South Loop
A ticketed costume ball with a costume contest, held in a hotel with a long reputation for being haunted.
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Every listing here is checked by hand against the organizer’s own page. Dates and times still change, so click through before you make the trip. Listings checked October 5, 2026.