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The Editorial Team

Fall Events Around Chicago: What to Do This Season

Written by our real estate broker Charlie Wood


Fall in Chicago is one of the most beautiful times of the year. The long, hot days of August give way to crisp mornings, mild afternoons, and a flurry of exciting seasonal activities. Football kicks off, fall colors dazzle, and pumpkin spice takes over everything! With summer travel winding down and school schedules in full swing, fall is the perfect time to explore all that Chicago has to offer.


As a Realtor in Chicago, I love keeping up with local events and sharing my favorite things to do around town. If you're looking to experience the best of what Chicago has to offer this fall, here are a few can’t-miss activities:


Oktoberfest in Lakeview

Contrary to popular belief, Oktoberfest is actually celebrated in September. So grab those Lederhosen and bring the whole family to Lakeview for a fun and scrumptious celebration of all things Bavarian, live music, and a craft beer tasting. 



Try out American Ghost Walks “Devil in The White City Bus Tour”, which is the original tour inspired by Erik Larson’s creepy true crime story. it's the perfect activity to get you in the Halloween spirit!



Apple Picking

Nothing says fall like apple picking! Try Apple Holler across state lines in Wisconsin or All Seasons Orchard in Woodstock to fill your baskets with fresh apples while enjoying a day in nature.


Foodies rejoice! Held at various locations around Chicago, Chicago Gourmet is a celebration of food, wine and spirits and is sure to make your taste buds dance this fall. Justice of the Pies is a participating Chef and Chicago-based bakery that specializes in sweet and savory pies, quiches and tarts.



The summer festival season may be winding down, but there’s still one party left- Riot Fest! So embrace your inner rocker and experience an eclectic lineup of live music in Douglas Park.



If supporting our museums are your thing, you can do no better than celebrating the enduring legacy and evolving future of the Field Museum!


As a Chicago Realtor, I understand the importance of not only finding the perfect home but also becoming part of the community. Whether you're looking for your next home or want to explore Chicago’s vibrant neighborhoods, I’m here to help. If you're interested in real estate opportunities or simply want to chat about the best fall spots in Chicago, don’t hesitate to reach out to me at charlie.wood@compass.com or 773-470-9873. You can always view our current listings on our team page here.


Have fun around town this fall and cheers! Charlie Wood.



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