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🗓️ Chicago · October 2026

Things to do in Chicago in October 2026

A few of the month's best festivals, parades, markets and nights out — 28 on Whosly's calendar in all. Dates marked "expected" follow the event's usual pattern and haven't been confirmed yet.

28dates in October
3free picks here
THRU
25
OCT

Chicago International Film Festival

Wed, Oct 14 – Sun, Oct 25 · Daily screenings, premieres and talkbacks · Multiple theaters · Citywide

Twelve days of premieres, international competition films and red-carpet galas at theaters around the city. Buy single tickets or a multi-film pass.

🎬 Film
OCT
24
SAT

Arts in the Dark Halloween Parade

Sat, Oct 24 · 6-8 p.m. · Columbus Drive, Grant Park · Grant Park / Loop

A nighttime Halloween parade of giant puppets, lanterns, stilt walkers and fire performers down Columbus Drive, with Buckingham Fountain behind it. Free, 6–8 p.m.

🎃 HalloweenFree
OCT
24
SAT

Chicago Bulls Home Opener

Sat, Oct 24 · vs. the Washington Wizards; tip time not posted · United Center · Near West Side

The Bulls play their first United Center game of the season, against the Washington Wizards and No. 1 pick AJ Dybantsa.

🏟️ Sports
OCT
24
SAT

Día de los Muertos Xicágo

Sat, Oct 24 · 3-8 p.m., rain or shine · Harrison Park (next to the National Museum of Mexican Art) · Pilsen

The museum's Day of the Dead gathering in Harrison Park: community ofrendas, pan de muerto, hot chocolate, music and face painting. Free.

🌎 Culture & heritageFree
OCT
31
SAT

Haunted Halsted Halloween Parade

Sat, Oct 31 · Block party 11 a.m.-6 p.m.; parade 7-8 p.m.; costume contest and after-party 8-10 p.m. · Halsted Street · Northalsted (Lakeview)

Northalsted's Halloween night: an all-day block party on Halsted, a 7 p.m. parade with bands and fire performers, and a costume contest. Free.

🎃 HalloweenFreeAll ages
🗓️

22 more Chicago dates in October in Whosly

Every date in the Chicago Festivals & Events list — star the ones you're into and see which friends are going.

🙋 The Whosly app

Never miss what's on in Chicago

These are a few of the dates in Chicago Festivals & Events — 200+ a year, plus 1,800+ concerts. The app keeps all of them, and tells you when it matters.

  • ✓Star a date for reminders — the morning of, before it starts, and when presales and on-sales open
  • ✓See which friends are interested, and let them see you
  • ✓Turn any date into a plan: text one link and see who's in — friends RSVP with no app
  • ✓Pair it with the city's best spots and happy hours, all on one map
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City Packs in the Whosly app: Chicago Festivals & Events with upcoming dates, Chicago Essentials and Deep Cuts
City Packs in the app
FAQ

Chicago in October

What is there to do in Chicago in October?
Highlights include Chicago International Film Festival (Oct 19), Arts in the Dark Halloween Parade (Oct 24), Chicago Bulls Home Opener (Oct 24), Día de los Muertos Xicágo (Oct 24) and Red Bull Setlist featuring Lil Yachty (Oct 24).
What free events are in Chicago in October?
Arts in the Dark Halloween Parade, Día de los Muertos Xicágo and Haunted Halsted Halloween Parade — all free.
Plan ahead

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