The Best Fall Festivals in Chicago

Fall in the Windy City brings cool breezes and falling leaves. That’s why the fall season is the best time to get out and about and attend some of the best Chicago Fall Festivals. With opportunities to sip on cider and hot chocolate, pick apples and pumpkins and even take part in a bar crawl, you can’t go wrong with this list of fun things to do in Chicago in the Fall.

Harvest Day

Garfield Park Conservatory in Chicago.

Each fall, the Garfield Park Conservatory hosts a Harvest Day to celebrate the autumn harvest. This Chicago event gives you a chance to learn more about the sustainable methods used by local farmers while also learning more about how to care for bees, goats and more. This Chicago festival features demonstrations on how to harvest organic vegetables and fruits, make a compost and feed your family organically. This Chicago attraction is a great spot for families year round, but you won’t want to miss out on the interactive games and activities at Harvest Day.

Fall Fest at Lincoln Park Zoo

From late September to late October, you can see the Lincoln Park Zoo in a new light. This Chicago fall festival offers families a chance to tour the zoo together while also climbing a hay mountain, lounging in the corn pool or riding the Ferris wheel. Featuring inflatables and even a large slide for all ages, the fall fest at Lincoln Park Zoo tops the list of fun things to do in Chicago.


Satisfy your sweet tooth and sip on warm apple cider when attending the Applepalooza Chicago Fall Festival. Hosted at the Chicago Women’s Park and Garden on S. Indiana Avenue, this Chicago event offers an apple food court with snacks and meals enriched with apples, as well as hay rides, interactive games for the kids and storytelling. As your surrounded by the beauty of this Chicago park and garden, you can also enjoy the live musical entertainment at this Chicago fall festival.

Chicago Wine Fest

What better way to spend the fall in Chicago than to mingle with friends while sipping on sweet wine? You get to do just that at the Chicago Wine Fest, held each year in early December. Known for its ‘elevated wine tasting experience,’ this Chicago fall festival quenches your thirst and gives you an opportunity to sample wines from local and national vendors. Live music and dining options are also available.

The Windy City is home to a variety of fall Chicago events and festivals, but the one thing that remains the same each year is the warm and inviting feel of the downtown area and surrounding neighborhoods. Dive into the Chicago culture and meet the locals when attending one of these popular Chicago festivals. Check back often for even more Chicago attractions.

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