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The Only Chicago Fall Events List You Need!
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items Leaf-peeping and city vibes collide in Chicago this fall! Dive into the only events list you need for autumn 2025
Sections
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October
November
October
Cruise the Chicago River while the guide tells of spooky tales of the city! All along with viewing the gorgeous nighttime view of the skyline!
Chicago Creepy Cruise
This is my personal favorite, as it is close to the city, never too crowded and has a ton to do! From U-pick sunflowers, pumpkins, Bee Yurt tours, Barnyard Jams (live music while you have a picnic), a HUGE corn maze, tractor ride, kids farm and count...
Family Fun At County Line Orchard!
See people from around the world come to run one of the most prestigious marathons in the WORLD! Get up early, take the kids, or ride solo and look for the fun signs!
Chicago Marathon 2025: Schedule & Spectator's Guide | Choose Chicago
Although not specific to fall, this Mob Tour is SO fun and shows where Al Capone, Hymie Weiss, John Dillinger and The Untouchables all hung out in the Windy City.
Chicago Crime and Mob Bus Tour
This free parade was ranked in the Top 10 by Fodor's!
Haunted Halsted Halloween Parade • Northalsted Business Alliance
This pop up has grown so much since it's inception just a few years ago. it's a must-see and great for kids and adults of all ages! Fair games, fall food, picture opportunities, the fun is endless.
Jack's Pumpkin Pop-Up | Chicago's Largest Fall Pumpkin Patch
You can't get more fall than Lincoln Park, with it's sprawling and beautiful park and view of the lake and beautiful fall trees. Pair with wine and you have the perfect fall activity!
Lincoln Park Wine Fest
The Loop closes to only pedestrian traffic from Randolph to Jackson and transforms the downtown into a block party with local business owners, artists and more. Great fun for kids and adults of all ages!
Sundays on State
“From family-friendly Fall Harvest Fests, and pumpkin patches, to haunted houses, parties, and more, there is something for everyone this season in the parks.”
Halloween At The Chicago Parks (Free!)
Although this is the most popular on the list, it is for a reason. SO much to do, from a petting zoo, pig races, live music, a sunflower farm, corn maze, pumpkin launching.. it's well worth the drive!
Kuipers Family Farm
Although it's 65 miles from the city, it's well worth it to pack the family up and explore over 50 varieties of apples, pecans, peaches and pairs! There's a restaurant, a children's park and a farm!
Apple Holler | Apple Picking Orchard in Wisconsin Near Chicago
Over 160 Acres of farmland including a playground, petting zoo, tree-maze, train rides, a carousel, country store and a bakery!
Fall Festival | Stade’s Farm & Market
This you-pick apple farm has many new attractions just added in 2023, this family-owned farm has a pumpkin patch, corn maze, corn box, ropes course, Bee Lines, and Barnyard Ball Zone.
All Seasons Orchard | 30 Years of Fall Family Fun
November
This legendary festival has floats, flying balloon characters similar to the Thanksgiving Parade in NYC, but on a smaller and less stressful scale. Grab a cider or hot chocolate, scoop up the kids and bring the family!
Magnificent Mile Lights Festival
Chicago Botanic Garden's Lightscape is stunning and SO mesmorizing. Great fun for the whole family!
Chicago Botanic Garden Lightscape
Just like NYC's, but on a smaller scale and much less stressful. Bring the whole family to this iconic Chicago event.
Your guide to the Chicago Thanksgiving Parade 2024 | Choose Chicago