Soak in the Last of Chicago Festival Season with These October Food Events
Meredith Francis
September 29, 2025
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As Chicago summer transitions to autumn, the city’s busy festival season is beginning to wind down. But there are still plenty of opportunities to enjoy the crisp air this October – which is all about the beverages. Explore the events below, and always be sure to check ticket information and times before you head out the door.
Oktoberfest (Naperville)
Friday, October 3 and Saturday, October 4 | Naper Settlement, Naperville
Naperville’s Oktoberfest returns with traditional German cuisine and beer, plus activities including music and a beer stein holding contest.
Lincoln Park Wine Fest
Friday, October 3 through Sunday, October 5 | Jonquil Park, 1001 W. Wrightwood Ave.
This wine festival returns to Jonquil Park in Lincoln Park for its ninth year. The event features open-air wine tastings and plenty of food options.
Lincoln Square Ravenswood Apple Fest
Friday, October 3 through Sunday, October 5 | Lincoln Avenue between Lawrence and Sunnyside avenues
This longstanding tradition returns for its 38th year with ciders and apple treats aplenty.
Cider and Ale Festival
Saturday, October 4 | Morton Arboretum, Lisle
Sample more than 60 varieties of cider and seasonal beers among the changing leaves at the Morton Arboretum.
Villa Park Brewfest
Saturday, October 4 | Cortesi Veterans Memorial Park, Villa Park
This celebration of beer returns to Villa Park for its 8th year with more than 80 craft beers and hard ciders.
Andersonville Fall Wine Walk
Sunday, October 5 | Various Locations, Clark Street
Local businesses in Andersonville serve as the wine tasting venues for this community event.
Hinsdale Wine Walk
Thursday, October 9 | Downtown Hinsdale Business District
Sample red, white, and sparkling wines at various businesses in downtown Hinsdale.
Stews & Brews
Saturday, October 11 | Port Clinton Square, Highland Park
Enjoy the ideal cold weather comfort food, including “chili, pozole, lamb stew, beef stroganoff, Hungarian goulash, potpies, and a variety of soups” at this event in Highland Park.
Oktoberfestiversary
Saturday, October 11 and Sunday, October 12 | Ravenswood and Belle Plaine avenues
Dovetail and Begyle’s annual celebration returns to the Ravenswood Avenue corridor for this event, which doubles as a fundraiser for The Friendship Center.