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Neighborhood Guides

🎃 Your guide to October

Posted on October 2

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.

City Cast

Your Guide to October 2026 in Chicago

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Your Guide to October 2026 in Chicago

A native dancer wearing a large black, green and yellow feathered headdress and colorful traditional clothing performs with one arm raised, holding a feathered ceremonial object. Other dancers in feathered headdresses are visible in the background.

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 Peoples’ Day

Get a head start with Tierra Colombiana Dance Ensemble’s Indigenous Peoples’ 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 Peoples’ 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 – as of now – 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 “Green Bay sucks” all year long. I’m sure that weekend won’t 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. Don’t sleep on broader Illinois’ fall colors. Check out this interactive fall foliage trip planner.

Fall Fests

Chicago Fall Fest kicks off Oct. 16, but there’s plenty of autumn celebrations happening across the city.

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:

In the News

All month long, we’ll continue following City Hall’s tense budget process, the race for Chicago’s first fully elected school board, and everything you need to know for the general election on Nov. 3. Stay tuned!

Team Tips and Picks

A large skeleton decoration reaching up in front of a purple lit home with other halloween decorations

Halloween decorations outside an Andersonville home. (Beata Zawrzel / NurPhoto via Getty Images)

Every month, the City Cast Chicago team tells you what we’re eating, where we’re shopping, and what else we’re planning for.

Michelle: Halloween and Día de los Muertos

I love walking around different neighborhoods, admiring the Halloween decorations. I’ll be setting up my altar throughout the month and visiting the National Museum of Mexican Art’s 40th annual Día de los Muertos exhibit. I’m excited to check out the stunning Día de Los Muertos Xicágo community ofrenda project Oct. 24.

Jacoby: New Restaurant

I’m really excited for the opening of Hooligan, Chef Christian Hunter’s Neo-Midwestern Bistro. This is the Michelin-awarded chef’s first brick-and-mortar. Funny story: I booked a table for Hunter’s 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, I’m looking forward to overdue friend dates and solo side quests to discover new hobbies. I can’t wait to see my friends perform in “Hayward” at Steppenwolf. And the Chicago Public Library’s maker spaces are gonna hate to see me coming because once I take 3D Printing 101, I’ll practically be living there!

Tickets to Get Now (Before It’s Too Late)

Wishing you a festive, cozy, and spooky October!

— Michelle Navarro

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