Can you believe summer is already almost over? There’s no need for tears, however, because the fun in Chicago just carries right into fall!
This autumn, there’s no shortage of exciting events happening around the Windy City, from the largest local pumpkin patch to music festivals, fall carnivals, fashion week, and more.
Here’s your ultimate bucket list of fall events in Chicago!
Chicago’s biggest pumpkin patch pop-up is back this September, just in time for spooky season!
The 2026 edition of Jack’s Pumpkin Pop-Up will feature Chicago’s largest corn maze, festive food and beverage options, carnival games, axe throwing, photo ops, and other activations.
Tickets are set to drop soon, click here to join the waitlist.
Chicago’s second-largest music festival after Lollapalooza returns to Douglass Park this September!
Riot Fest promises three days of the best acts in rock n’ roll, punk, and alternative music.
Big names headlining the 2026 festival include Alanis Morissette, The All American Rejects, Iggy Pop, Pierce the Veil, and dozens more.
Single and three-day passes are still available here.
This fall in Chicago, the world of Minecraft comes to life with the Minecraft Experience: Villager Rescue in Rosemont.
This immersive experience challenges participants to explore 8 different Minecraft rooms, mining for gems, fighting spiders, and collecting treasure along the way.
It’s the ultimate interactive gameplay experience for families and kids of all ages!
Chicago’s favorite end-of-summer tradition, Jazz Fest, returns to Millennium Park this Labor Day Weekend.
The 2026 Jazz Fest lineup boasts four days of free programming and headlining performances from big names including Robert Glasper and Dee Dee Bridgewater.
Taste of Polonia
A little piece of Poland arrives in the Midwest this September, with the 2026 edition of Taste of Polonia!
Chicago’s largest Polish cultural festival will feature a full weekend of authentic food and beverage, live music, traditional dancing and art activations, carnival rides, and other family-friendly fun.
Murder on the Rocks: A Murder Mystery Cocktail Experience is taking over Chicago’s historic Stan Mansion for one night this fall.
The immersive pop-up combines a vintage speakeasy experience with an interactive murder mystery game, with all participants playing a role in solving the crime.
Tickets include three craft cocktails throughout the 75 minute duration.
Arc Music Festival
Arc Music Festival is taking over at Union Park in West Town this Labor Day Weekend, with four days of the biggest acts in house and electronic music.
Tickets for the high-energy festival are still available, grab yours here.
Fall festivals at Parkway Bank Park
Fall in Chicago means festivals galore at nearby Parkway Bank Park in Rosemont!
This September, Chicagoans can head to the entertainment district for three fall festivals:
- Battle of the Bags cornhole tournament – September 6
- Family Fall Fest – September 12
- “Rosetoberfest” – September 26
And the best part? All three fests are free to enter!
Chicago Marathon
Thousands of runners will take to the street this October for the 48th annual Chicago Marathon!
Even if you’re not participating in the race yourself, you can still show up to witness the spectacle while cheering on your friends and neighbors.
View the full course map and learn more information here.
Illumination at Morton Arboretum
Morton Arboretum’s annual Illumination light show returns this fall, opening to the public on November 14.
The 2026 celebration is the arboretum’s most ambitious yet, featuring a Northern Lights-inspired canopy and more than 22 light displays.
Tickets go on sale this October, learn more here.
Serial Killer: The Exhibition World Tour is a gripping, immersive true-crime experience featuring the world’s first and only collection of authentic artifacts connected to history’s most notorious serial killers.
Following its massive success in London, Paris, and Berlin, and fresh off its U.S. premiere in Atlanta, Chicago is officially the second stop of this blockbuster American tour.
Built on ten years of research and collaboration with over sixty global collectors, this expanded landmark exhibition features over 2,100 authentic artifacts while introducing exclusive Chicago content exploring the city’s dark criminal history, including dedicated sections on H.H. Holmes and John Wayne Gacy.
Chicago Fashion Week returns for its third edition this October, and the 2026 event is bigger and better than ever.
Fashion aficionados will enjoy a stacked lineup of citywide activations including fashion shows, clothing markets and swaps, workshops, and even a special runway exhibition at “The Bean.”
View the full lineup and learn more here.
Chicago International Film Festival
The 62nd annual Chicago International Film Festival is back this October 14-25, with an exciting schedule of film screenings at venues around the Windy City.
Highlights of the 2026 event include appearances from hometown hero Bob Odenkirk and director Tim Blake Nelson, plus the world premier of the locally-produced documentary “Ever After.”
Early-bird passes are on sale now, learn more here.
