Do you feel that crisp air, Chicago? Because I do, and I love it. Fall sometimes feels just as fleeting as summer. Luckily, we have a full guide on how to make the most of October in Chicago.
Your Guide to October 2026 in Chicago

A member of Huehuecoyotl, an Aztec dance group, dances during an Indigenous Peoples' Day celebration at the Field Museum. (Eileen T. Meslar/Chicago Tribune/Tribune News Service via Getty Images)
Indigenous Peoplesâ Day
Get a head start with Tierra Colombiana Dance Ensembleâs Indigenous Peoplesâ Day Celebration with dance, music, and storytelling at Harrison Park on Oct. 10. Then, visit the recently reopened Gichigamiin Indigenous Nations Museum in Evanston for their Indigenous Peoplesâ Day Celebration on Oct. 12 to learn more about Indigenous histories and for guided craft activities.
Fall Sports
Chicago hockey is back! Watch a Blackhawks game at the United Center. Bulls start their regular season against the Wizards Oct. 24. Congratulations to the White Sox, who have â as of now â kept October baseball alive in Chicago. For my soccer fans, the Stars are back in Evanston for three straight games, while the Fire have four home games at Soldier Field this month. The Bears only have two as they prepare for the Jets this weekend, followed by our arch-nemesis, the Packers, on the road at Lambeau Field. Chicagoans have been chanting âGreen Bay sucksâ all year long. Iâm sure that weekend wonât be any different.
Peak Fall Foliage
Estimated peak times for Chicagoland are around the second week of October. Here are spots across the city to admire the seasonal changes. Donât sleep on broader Illinoisâ fall colors. Check out this interactive fall foliage trip planner.
Fall Fests
Chicago Fall Fest kicks off Oct. 16, but thereâs plenty of autumn celebrations happening across the city.
- Lincoln Park Zoo Fall Fest and Jack's Pumpkin Pop-Up open now til Nov. 1
- Island Party Hut Fall Fest on the Riverwalk on Saturdays
- North Centerâs Oktoberfestiversary Oct. 10-11
- Chicago Botanic Gardenâs Night of 1,000 Jack-o-lanterns Wednesdays to Sundays
Halloween in the City
Thinking of a costume? We've got some quick, Chicago-themed ideas! The Arts in the Dark parade returns to Columbus Drive Oct. 24 after outgrowing State Street. Here are some more spooky events going down:
- Oct. 24: Campfire Horrors at Big Marsh
- Oct. 25: Lincoln Scared trick-or-treating
- Oct. 28: Halloween Haunted Hallway at FranklinPark
- Oct. 28: Ravenswood Costume Crawl
- Oct. 30: Montrose Monster Mash
- Oct. 31: Haunted Halsted Halloween Fest and Parade
- Oct. 31: Haunted House at Columbus Park
- Oct. 31: Upside Down Halloween Parade at Washington Park
In the News
All month long, weâll continue following City Hallâs tense budget process, the race for Chicagoâs first fully elected school board, and everything you need to know for the general election on Nov. 3. Stay tuned!
Team Tips and Picks

Halloween decorations outside an Andersonville home. (Beata Zawrzel / NurPhoto via Getty Images)
Every month, the City Cast Chicago team tells you what weâre eating, where weâre shopping, and what else weâre planning for.
Michelle: Halloween and DĂa de los Muertos
I love walking around different neighborhoods, admiring the Halloween decorations. Iâll be setting up my altar throughout the month and visiting the National Museum of Mexican Artâs 40th annual DĂa de los Muertos exhibit. Iâm excited to check out the stunning DĂa de Los Muertos XicĂĄgo community ofrenda project Oct. 24.
Jacoby: New Restaurant
Iâm really excited for the opening of Hooligan, Chef Christian Hunterâs Neo-Midwestern Bistro. This is the Michelin-awarded chefâs first brick-and-mortar. Funny story: I booked a table for Hunterâs previous version of Hooligan inside Time Out Market back in January, but it was cancelled at the last minute with little explanation. A week later, Time Out Market announced they were shutting down. So this is a resy 10 months in the making.
Chima: Quality Time and Crafting
This month, Iâm looking forward to overdue friend dates and solo side quests to discover new hobbies. I canât wait to see my friends perform in âHaywardâ at Steppenwolf. And the Chicago Public Libraryâs maker spaces are gonna hate to see me coming because once I take 3D Printing 101, Iâll practically be living there!
Tickets to Get Now (Before Itâs Too Late)
- Oct. 2: Live Pro Wrestling | Logan Square Auditorium
- Oct. 3: Cristian Castro | Rosemont Theatre
- Oct. 4: RnB Rooftop Party | Utopian Tailgate | Old Town
- Oct. 6: Blackhawks home opener | United Center | Near West Side
- Oct. 8: Don Omar | Allstate Arena | Rosemont
- Oct. 8: The Moth GrandSLAM Championship | Athenaeum | Lakeview
- Oct. 8-18: Chicago Fashion Week | Multiple locations
- Oct. 9-11: Lincoln Park Wine Fest
- Oct. 17: Jesse Welles | Salt Shed
- Oct. 18: Radical Used Book Fair | Haymarket House | Uptown
- Oct. 24: Bulls home opener | United Center | Near West Side
- Oct. 24: Waking the Witch | Empty Bottle | West Town
- Oct. 30-31: Sanctum Dark Music Festival | Thalia Hall | Pilsen
Wishing you a festive, cozy, and spooky October!
â Michelle Navarro


