Fun Fall Activities To Do In Chicago

Chicago is not a city best known for it’s Fall season, it’s often hazily transgressed by the Midwest masses still reeling from the shock that summer is truly over and the lethargic acceptance that the 6.5-month Winter season is around the corner. However, this year, Chicago has had the chance to experience a few glorious weeks of full Fall foliage, fuzzy sweaters, and pumpkin-spiced everything. We at FG know it’s important to get out the house while we still can and while it’s still safe. Thus, we’ve compiled a list of some Fall activities you can participate in, drive through, drive up, or visit virtually. Don’t forget your masks and hand sanitizer!

Private rooftop deck: This isn’t just any private rooftop deck. It’s the largest in the nation. The Old Post Office location has granted the public to use the 3.5 acres of outdoor space in the time to enjoy the outdoors during the coronavirus pandemic. “The rooftop includes a quarter-mile running and walking track; three-season, heated bar, and pavilion; basketball court; heated paddle tennis courts for winter play; and landscaping that includes more than 40,000 plants and trees, with 58 varieties.” The newly renovated, historical space runs alongside the Chicago River, at 433 W. Van Buren St. The building previously sat unused for more than two decades until last Fall.  


Bike Rides: There are some surprisingly delightful bike paths in Chicago. The lakefront remains a favorite of many for good reason, it’s undesirably beautiful!  However, for a path less take try the Green Bay Trail. Heads up, it’s a bit of a longer ride. Some of these rides even take you to The Pavilion at Ravinia for those that miss the outdoor concert space.


Get Lost In a Corn Maze: Did you know that Illinois is home to the world’s largest corn maze?! Yup, Richardson Adventure Farm offers a full day of activities for the entire family. Even better, it’s an opportunity to build teamwork, get some critical thinking in, and stretch those legs! They also offer pumpkin picking and a zipline!


Oktoberfest: When Chicago is beautiful it can be magical. Take advantage of the last few days of decent weather and enjoy Oktoberfest if you’re feeling comfortable enough to be out. Be sure to make a reservation and dress appropriately for both the festivities and for potentially finicky Chicago weather. Be the best dressed by bringing along hand sanitizer and extra face masks, just in case. 


Experience Fall Foliage: Beat the crowds, or a schedule altogether, and experience the very best of Illinois’ Fall foliage in full bloom by driving along or to one of these trails! You can find a more exhaustive list here but some of our favorites include Garden of the Gods and Great River Road which has over 500 miles of views you’ll never forget.


Apple Picking: Orchard visits are a Fall favorite of many for good reason. There are several locations around Chicago to choose from, both a short drive or a long trip. Don’t forget to pick up apple cider doughnuts on your way out!


Drive-In Movie Theaters: Miss seeing movies in a theater with your loved ones? Yup, same here. Luckily, Chicago has come up with a solution. Drive-in movie theaters! They are popping up all over Chicago and some even offer a full snack service. Be responsible and stick to a non-alcoholic drink if you decide to take advantage of the bar option or secure a designated driver among your group to ensure you can thoroughly enjoy the drive-in experience. 


Virtual races: If you’re sad that the coronavirus has stolen your race activities from you this Fall, fear not. There are plenty of upcoming virtual races you can register for. Even better, many of the race proceeds go to good causes. 



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