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

Chicago’s fall season brings exciting festivals and events across the city. From various fun activities at different zoos in the city to pumpkin patches and drink festivals, there’s something special for everyone.

Sept. 18 - Nov. 2: Jack's Pumpkin Pop-Up

Jack's Pumpkin Pop-Up returns to Goose Island from Thursday, September 18, through Sunday, November 2, billing itself as Chicago's largest fall festival for all ages. September hours run Monday-Friday 5-10 p.m., Saturday 12-11 p.m., and Sunday 12-10 p.m., while October extends schedules with Monday-Friday 4-10 p.m. and weekend hours starting at 11 a.m. The downtown Chicago venue welcomes all ages with drinking for 21+ and axe-throwing for 18+, according to the pop-up’s website information.

Sept. 20: Zoo After Dark

Brookfield Zoo Chicago kicks off fall festivities on Saturday, September 20, with Zoo After Dark: Animal Adoption Adventure from 4-8 p.m. This unique evening experience lets families see animals under the stars while enjoying live music by Feel Good Party Band. The event includes free carousel rides, free parking, zoo chats, and special animal adoption deals, as detailed in the zoo's programming. Visitors can also participate in scavenger hunts and get behind-the-scenes looks at animal nutrition care, according to the zoo's event information. Secure Brookfield Zoo attraction tickets now before they’re gone.

Sept. 26: Lincoln Park Zoo Fall Fest

Lincoln Park Zoo launches its Fall Fest on Friday, September 26, running through Sunday, October 26, with free admission for all ages. 

Families can pick pumpkins, roast s'mores, and enjoy rides, including the Giant Fun Slide and Ferris wheel. The zoo's seasonal celebration includes professional pumpkin carvers and fall-themed animal enrichment activities, as noted in the festival details. 

Ticketed attractions feature inflatables and fall pop-ups with classic autumn activities, according to the zoo's fall programming.

Sept. 27: Hispanic Heritage Fest

Brookfield Zoo continues celebrations on Saturday, September 27, with Hispanic Heritage Fest from 10 a.m. to 6 p.m. This new festival features live music, cultural performances, and storytimes with local authors at Hamill Family Nature Plaza. Traditional dance performances by Ballet Folklórico Sones Mexicanos and Huehuecóyotl highlight the day's cultural programming, as outlined in the festival schedule. The event includes workshops on tissue paper flower making and cybersecurity, plus Spanish-language animal chats about creatures from Spanish-speaking regions, according to the zoo's Hispanic Heritage programming. Grab your Brookfield Zoo attraction tickets before they all sell out.

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Oct. 3-5: Lincoln Park Wine Fest

Lincoln Park Wine Fest transforms Jonquil Park from Friday, October 3, through Sunday, October 5, into an open-air wine market for its eighth 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. The event also seeks volunteers aged 21 and up to help staff wine tasting booths, as noted in the volunteer information.

Oct. 3-5: Lincoln Square Apple Fest 

Lincoln Square Apple Fest celebrates its 38th year from Friday, October 3, through Sunday, October 5, 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. This long-standing festival marks the beginning of the season in Lincoln Square, as organized by the Lincoln Square Ravenswood Chamber of Commerce.

Oct. 4. Chicago Beer Festival 

The Chicago Beer Festival takes over the Field Museum on Saturday, October 4, from 7-11 p.m., featuring over 65 breweries with fall seasonal beers. Early admission costs $70 and includes entry at 7 p.m. with specialty beers, while general admission is $55 starting at 8 p.m., according to festival organizers. The museum exhibits remain open to attendees during this unique brewery showcase, with food sold separately and no tickets available at the door, as detailed in the event programming.

Oct. 11: Zoo Fiesta with Latin theme

Lincoln Park Zoo hosts Zoo Fiesta on Saturday, October 11, from 6-10 p.m. for ages 21 and up at $20 admission. This Latin-themed event celebrates cultures of Central and South America with sugar skull decorating and dance performances by the Center of Peruvian Arts. The evening features Spanish-language animal chats about native wildlife, free rides on carousel and Ferris wheel, plus specialty food, including tacos and tamales for purchase, as detailed in the event programming. DJ Omarcillo will spin tunes all night while indoor and outdoor bars serve guests, according to the fiesta schedule.