Chicagoland Fall Festivals You Won't Want to Miss

Our real estate agents love fall in Chicagoland. Time to enjoy the crisp breeze, sip a pumpkin latte from one of our favorite Chicago coffee shops, and check out some of the fall festivals and events that pop up this time of year. If you really want to get into the spirit of the autumn season, you'll have ample opportunity to do so in Chicago this fall. 

Sonny Acres Farm Fall Fest - West Chicago, IL

Address: 29W310 North Ave, West Chicago, IL 60185

West Chicago's Sonny Acres Farm is the place to be this season. Their annual Fall Fest runs from September 14 through October 30 and offers an incredible array of seasonal activities, including a pumpkin patch, petting zoo, carnival rides, games, haunted barn activities, and hay wagon rides. Sonny Acres Farm's Fall Fest also includes a wide array of tasty food and drink, farm stand produce, and souvenirs. Live music also takes place throughout the festival season, so be sure to check the farm's online calendar!

Oktoberfest Chicago - Chicago, IL

Address: 1429 W Wellington Ave, Chicago, IL 60657

Oktoberfest Chicago returns on September 26-28 with some of the best traditional Bavarian fun in Chicagoland. A staple for 20-plus years, the festival includes live oompah bands and dancing, traditional German food, and plenty of beer from local and international brewers. Oktoberfest Chicago is hosted by St. Alphonsus Church. 

Fall Fest - Chicago, IL

Address: 2001 N Clark St, Chicago, IL 60614

Always family-friendly and free of charge, Fall Fest at the Lincoln Park Zoo offers a month-long calendar of harvest season festivities from September 26 to October 26. It's one of Chicago's best options for kids and adults alike to experience the autumnal spirit. The festival features rides, attractions, and entertainment, along with pop-up events such as pumpkin picking and s'more toasting.

Jack's Pumpkin Pop-Up - Chicago, IL

Address: 1265 W Le Moyne St, Chicago, IL 60642

Jack's Pumpkin Pop-Up is arguably the biggest fall event of the year in Chicago, and the 2025 incarnation of this beloved festival is shaping up to be the biggest yet. Taking place on Goose Island near Downtown Chicago, Jack's Pumpkin Pop Up starts in September and includes a pumpkin patch made up of over 10,000 pumpkins. Other highlights include Chicago's largest corn maze, axe-throwing, and carnival games.

Lincoln Square Ravenswood Apple Fest - Chicago, IL

Address: 4703 N Lincoln Ave, Chicago, IL 60625

Encompassing a long stretch of Lincoln Avenue between Lawrence and Sunnyside, the 38th Annual Apple Fest will return this year to the Lincoln Square and Ravenswood neighborhood. This long-running outdoor street festival takes place on October 3-5 and includes live music, food and drinks, artisan vendors, and a wide range of games and entertainment for all ages. Don't miss out on an amazing menu of cider and apple-inspired dishes!

Fall Color Festival - Lisle, IL

Address: 4100 IL-53, Lisle, IL 60532

Every year around this time, the Morton Arboretum in Lisle puts on a Fall Color Festival that highlights the changing colors of the Illinois landscape. The Morton Arboretum is a 17,000-acre botanical garden in Chicago's western suburbs, and its tree-filled landscape is the perfect place to watch the fall colors progress. The Fall Color Festival extends through the season and includes a variety of events, including a Cider and Ale Festival on October 4 and a 5K Run on October 25.

Contact us today to learn more about what's happening in Chicagoland this fall. Our real estate agents are here to be your guides to life in the Chicago area.