The ultimate guide to fall fun, festivals & events in Chicago

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Chicago’s fall season has officially arrived, bringing exciting festivals and events across the city. From various fun activities at different zoos in the city to pumpkin patches and corn mazes, there’s something special for everyone.

Jack's Pumpkin Pop-Up & Corn Maze

Jack's Pumpkin Pop-Up returns to Goose Island from Saturday, Sept. 19, through Sunday, Nov. 1, billing itself as Chicago's biggest fall festival that features 10,000+ pumpkins. The downtown Chicago venue welcomes all ages with drinking for 21+ and axe-throwing for 18+. Other highlights include Chicago's largest corn maze and gem mining. Get tickets on the organization's website.

Goebbert’s Pumpkin Farm

Open all year-round, Goebbert's Pumpkin Farm is currently hosting its annual Fall Festival through Sunday, Nov. 1. Attractions include a corn stalk maze, pony and camel rides, duck derby, pig races, and wagon rides. The farm offers a 10-room haunted house for more daring visitors. Additionally, the farm's Animal Land allows guests to explore exotic animals such as kangaroos, zebras, llamas and more. 

Richardson Adventure Farm’s World’s Largest Corn Maze opens image one

Drone image showing Richardson "World's Largest" Corn Maze for 2026, a celebration of America 250 | Photo by George Richardson

Richardson Adventure Farm's "World's Largest" Corn Maze

The "World's Largest" Corn Maze has returned to Richardson Adventure Farm in Spring Grove, Ill., featuring 28 acres and 9.7 miles of trail. This year's maze is themed to celebrate America250 with a design that depicts signers of the Declaration of Independence, a Betsy Ross flag, an American Eagle, and other patriotic images. The farm will remain open through Sunday, Nov. 1.

The ultimate guide to fall fun, festivals & events in Chicago

Photo by Lincoln Park Zoo

Lincoln Park Zoo Fall Fest

Lincoln Park Zoo launches its Fall Fest on Friday, Sept. 25, running through Sunday, Nov. 1, with free admission for all ages. Families can pick pumpkins, watch professional pumpkin carvers, roast s'mores, and enjoy rides, including the Giant Fun Slide and Ferris wheel. The zoo's seasonal celebration includes fall-themed animal enrichment activities and plenty of fall treats. 

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The ultimate guide to fall fun, festivals & events in Chicago

Image by Lincoln Park Zoo

Lincoln Park Wine Fest

Lincoln Park Wine Fest transforms Jonquil Park from Friday, Oct. 9, through Sunday, Oct. 11, into an open-air wine market for its 10th annual celebration. The festival runs Friday 5-10 p.m., Saturday 11 a.m.-10 p.m., and Sunday 11 a.m.-7 p.m. at 1001 W. Wrightwood Ave. Ticketed wine tastings showcase many varieties while food pavilions offer seasonal treats, according to festival organizers. 

Lincoln Square Ravenswood Apple Fest 

Lincoln Square Ravenswood Apple Fest celebrates its 39th year from Friday, Oct. 2, through Sunday, Oct. 4, along Lincoln Avenue between Lawrence and Sunnyside. The community tradition runs Friday 3-7 p.m. and weekend hours 9 a.m.-6 p.m. with a suggested $5 donation, bringing neighbors together for autumn's start. 

The ultimate guide to fall fun, festivals & events in Chicago

Image by Lincoln Park Zoo

Morton Arboretum's Glass Pumpkin Patch

In a more unique, dazzling twist to pumpkin patches, Morton Arboretum will host its 16th annual Glass Pumpkin Patch starting Friday, Oct. 9, through Sunday, Oct. 11. Discover more than 8,000 glass pumpkins of all shapes, sizes, and colors. Not only can visitors shop the pumpkin patch, they can also view glassblowing and flameworking demonstrations.

Morton Arboretum’s Glass Pumpkin Patches opens in October

Photo by The Morton Arboretum

Happy Times Pumpkin Fest

Starting Wednesday, Sept. 16, through Saturday, Oct. 31, Happy Times Pumpkin Fest will bring all the fun fall favorites to Didier Farms in Lincolnshire, Ill. Purchase pumpkins and autumn merchandise, go on amusement rides, and enjoy apple cider donuts, fudge and other fall treats.

 

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