Chicago Fall Festivals

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September 1, 2022 @ 8:00 am - November 30, 2022 @ 5:00 pm CDT

Chicago may be called the second city, but savvy travelers know that its Fall festivals in Chicago deserve to be someone’s first choice! So whether you wish to greet the cooler months with a cold brew or a caramelized apple, Windy City is full of autumnal delights.

Sip cider while listening to jazz tunes at Hyde Park or ponder the architectural marvel of the city. Fall in Chicago is unbeatable.

Follow along to discover the most-awaited Fall festivals in Chicago.

Fall Festivals in Chicago

Chicago German-American Oktoberfest

When: September 9 to 11, 2022

Located at Lincoln Square, this festival is one of Chi-town’s most awaited fall celebrations of all things German. Sip Bavaria’s and Chicago's best breweries, dance to oompah music, sample Bavarian cuisine, and more. Don’t forget to wear your lederhosen or a dirndl and raise a stein for the start of the autumn season!

Chicago Bourbon & Barbecue Fest

When: to be announced

Craving for a savory barbeque and barrel-aged bourbon? This finger-licking festival is a must-visit! Head to the Roscoe Village neighborhood to enjoy the Midwestern treats. Beyond smoked meats and refreshing drinks, you’ll experience lively performances from local bands at this seasonal revelry. 

Related Post: 3 Days in Chicago this Fall

Open House Chicago

When: October 1 to 31, 2022

The in-person visit is from October 15 to 16, 2022

Every October, Open House Chicago invites tourists and locals for a self-guided tour throughout the city. This free public festival puts a spotlight on over 20 neighborhoods, emphasizing their history and architectural wonders. There will also be programming, talks, and behind-the-scenes access to significant spots across Windy City. 

Hyde Park Jazz Festival

When: September 24 to 25, 2022

Enjoy the crisp, cool air while singing along to your favorite jazz songs at Hyde Park this fall. Over 30 world-class musicians like Billy Branch and Sadie Wood will be there to serenade you. This Chicago fall fest also features local culinary cuisines and drinks throughout the venue.  

More than 20,000 jazz aficionados are expected to arrive, so come early to reserve a good spot. There will be a $5 fee.

Lincoln Square Apple Fest

When: October 1 to 2, 2022.

Whether you’re into Honey Crisp, Gala, or fresh apples, you’ll have the best day at one of the sweetest fall events Chicago. This long-standing tradition brings the community together with live music, carnival games, and sweet eats. Sip spiced cider or enjoy a slice of pie while listening to eclectic performances. Make sure to bring your kids and play with them in the inflatable bounce castle. The fun will be held at Lincoln Square.   

crowd of people gathered in front of stage with band playing set up on middle of street at Apple Fest with stall on the side in Chicago, Illinois, USA

photo credit: The StingRays via Facebook

Chicago Beer Fest

When: October 8, 2022

Taking over the Field Museum, the Chicago Beer Fest treats guests with over 65 breweries. Fill yourself with authentic German goodness, from pretzels to pies and plenty of beer! This event also features traditional games and live performances, making it ideal for all ages. Prost!

Related Post: 10 Landmarks in Chicago You Don’t Want to Miss

Chicago International Film Festival

When: October 12 to 23, 2022

Named the longest-running film festival in North America, this is a cinephile’s oasis. The most-awaited fall fest Chicago showcases over 100 films from all over the world. Watch new-released documentaries, features, and short films here. Attendees can also enjoy and meet their favorite filmmakers, artists, and producers in the panels and Q&As.

Night of 1,000 Jack-o’-Lanterns

When: October 12 to 16, 19, and 23, 2022.

Marvel at the lit decorations this Halloween season. Over 1,000 hand-carved pumpkins, which professional artists sculpt, will greet you as you wander through the Chicago Botanic Garden. The gates open at 6 PM. This is one 

Other Attractions in Chicago

The Windy City is overflowing with charm. Have a blast during your trip with these other attractions:

Experience Fall Festivals in Chicago

Make the most of autumn festival Chicago with exciting and delicious festivals. Embrace the vibrant fall foliage, apple treats, and breathtaking colors.

Looking to see all the sights of Chi town? You can make a complete vacation with our great Chicago vacation packages.


September 1, 2022 @ 8:00 am CDT
November 30, 2022 @ 5:00 pm CDT
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Chicago, IL United States + Google Map

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