US Mom Blog

Things to do in the Fall in Chicagoland

Posted 3 years ago


September 1 – 4  - African Festival 

African Festival of the Arts celebrates African art, crafts, drumming, food, and entertainment at a festival Labor Day weekend in Washington Park. Annually during Labor Day Weekend, the Festival grounds in Chicago’s Washington Park come alive in a simulated African village. 

September 2 – October 15 - Circus in the park 

Midnight Circus in the Parks is a series of daytime shows on weekends at parks, perfect for families. Midnight Circus’s belief in live performance and its power to engage & inspire, entertain & educate, embolden & empower the audience, the community, and the world is on full display when the little tent goes up, the music flows out and the acrobats take the ring

  • Sept. 2 to 3 - Hamilton Park                  
  • Sept. 9 to 10 - McKinley Park
  • Sept. 15 to 17 - Wicker Park                  
  • Sept. 23 to 24 - Lake Shore Park
  • Sept. 30 to Oct. 1 - Kosciuszko Park

September 8 – 9 - Windy City Wine Festival

Sample more than 300 wines from around the world at the outdoor festival near Buckingham Fountain. Learn about new and exciting varieties of wine from the experts at this wine festival. Wine seminars and cooking demonstrations will be conducted by event sponsors, exhibiting wineries, area chefs and restaurateurs. Live music will be performed on the festival stage. The festival is the perfect opportunity for you to kick back, relax, and have a good time in Chicago.

September 8 – 10 - Chicago German-American Oktoberfest 

Free admission to Oktoberfest at Lincoln Square! Try authentic German food and traditional drinks. Dance to music of German bands and spend the evening with friends and enjoy a fabulous festival. You can check out the Oktoberfest parade on Saturday at 2pm at Lincoln Ave. Traditional singing and dancing groups from Chicago will perform on Saturday after the parade and on Sunday at 2pm.

September 22 – 24 -  Chicago Gourmet 

Millennium Park will be hosting a premium food and wine event with 100 chefs, cooking demonstrations, beer and food pavilions, and wine tastings. Chicago Gourmet will have live cooking demos, wine and cocktail seminars, book signings, and amazing tastings from the best restaurants, wineries, spirits purveyors, and breweries. Chicago Gourmet is celebrating ten years this year and to celebrate there will be anniversary surprises in store for attendees. 


October 1 -  Lincoln Square Ravenswood Apple Fest 

Usher in the fall at the Lincoln Square Ravenswood Chamber of Commerce's 30th Annual Apple Fest! Dozens of vendors participate in Apple Fest every year, selling everything from candy apples to scarves and hats. Pick up fresh apple pie, hot apple cider or even a whole bushel of apples - and for the first time ever learn how to prepare them at the Giddings Gourmet chef demos!  Lawrence Avenue Music Stage will be playing music you can dance and sing to. Kids can play in the Leland Avenue Kids Zone, featuring child-focused activities throughout the day. 

October 12 - Whiskey Tasting

The Union League Club is hosting this year’s Whisky Extravaganza, which includes unlimited tastes of more than 100 whiskies, culinary pairings, and master classes. Men are required to wear a jacket to the event, so you can make it a fun and fancy night out on the town. 

October 14-15 - Architectural Open House 

The Chicago Architecture Foundation’s Open House Chicago is a free public festival that offers behind-the-scenes access to more than 200 buildings across Chicago. Explore the hidden gems and architectural treasures of Chicago’s diverse neighborhoods—all for free. Tour soaring skyscrapers, repurposed mansions, opulent theaters, exclusive private clubs, private offices and breathtaking sacred spaces. 

October 28 - Halloween at the Zoo 

Kids can wear costumes, trick-or-treat, hear music, make crafts, and see a haunted house at Spooky Zoo Spectacular at Lincoln Park Zoo. Spooky zoo gives children the opportunity to celebrate Halloween in a free, safe, and family-friendly environment. This year’s celebration will mark the 31st anniversary of Spooky Zoo.

October 29  -  Race in Grant Park 

The Hot Chocolate 15K/5K and 2-mile walk begin and end in Grant Park and include hot chocolate. Marshmallow sweet stations are dotted along course routes and a Finisher Mug encourages the consumption of decadent fondue. 

October 31 - Halloween Parade 

Register and wear a Halloween costume to join the Northalsted Halloween Parade, or watch from the sidewalk on Halsted Street from Belmont to Addison. The Northalsted Halloween Parade is known throughout the nation for its outlandish costumes, creative programming, and entertaining parade. All are welcome to march in the parade! You can dress to impress and compete in the costume contest for theme, group, scariest, and drag. 


November 1-5 - Children’s Film Festival 

Come bring your kids to check out the 34th Annual Chicago International Children’s Film Festival! Billed as North America’s largest film festival for children, the Chicago International Children’s Film Festival showcases the best in culturally diverse, non-violent, value affirming new cinema for children and offers interactive workshops. 

November 12 - Family Lantern Festival 

The German International School Chicago (GISC) welcomes children of all ages and backgrounds to a fun-filled autumn celebration with crafts, singing, and a lantern parade. New this year, we will return to the DANK Haus after the parade to enjoy German dinner and drinks. A ticket to Latern fest and St. Martin’s Parade gets you a lantern kit to assemble and join the parade, with singing, crafts, dinner, and a bake sale at Dank Haus. 

Content submitted by the MOM team at Baird & Warner

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