Our Favorite Things to do in Chicago this Fall

Our Favorite Things to do in Chicago this Fall

Grab a pumpkin spice latte (or your autumnal drink of choice) and get excited, because fall in Chicago is easily one of the most dreamy, magical seasons. Between seasonal activities that only crop up during harvesttime and their fall-flavored food and beverage counterparts, there’s plenty to do and even more to taste. 

Our biggest issue with the season? It doesn’t last long. So, throw on a cozy sweater, pair fun socks with your favorite Bucketfeet, and crunch through those leaves to get in the fall mood. Make the most of your fall in Chicago with our list of must-do activities. 


Be Outside (While You Can)

No need to dwell on the impending doom of winter, but it’s worth noting—fall’s the best time to be outside in Chicago. The humidity is low, there’s a pleasant crispness in the air, and the foliage is stunning. Use your weekends this September, October, and November to explore parks in neighborhoods you rarely frequent. 

If you’ve been to Chicago even once, you’ve likely visited Millennium Park, home to the infamous Cloud Gate sculpture AKA The Bean. It’s worth walking the hotspot again, and downtown in general, during the changing seasons to take in fall colors with the city as the backdrop. While you’re there, walk the Lakefront Trail and enjoy the blustery sky swirling over cobalt water.  

Nearly every neighborhood has several worthwhile parks to wander this season. There’s the 606, a rejuvenated stretch of elevated rail beautifully maintained throughout fall, that cuts across Bucktown, Wicker Park, Humboldt, and Logan Square. Lincoln Park offers plenty of picnicking magic as well as the Lincoln Park Zoo (admission’s free!) and Lincoln Park Conservatory. Garfield Park on the city’s West Side and Jackson Park in Woodlawn are two impressive parks to explore this fall. Pack a picnic, wear layers, and find your new favorite fall-feeling park in the city.   


Get in the Seasonal Spirit

What better way to celebrate the season than with classic fall activities. Chicago’s got all the best the midwest has to offer in terms of charming, autumnal outings, great for groups of family or friends. Venture northwest to Prairie Sky Orchard or west to Honey Hill Orchard to pick your own bushel, hop on a wagon ride, and bask in the season’s glory. Apple picking in one of Illinois’ many orchards is a uniquely fall experience. 

Go full-on harvest and explore the wealth of pumpkin patches and corn mazes that the suburbs and surrounding towns have to offer. Dress up in costume to really embrace those fall vibes and enjoy finding the perfect pumpkin for carving, smelling the hay, and making unforgettable fall memories.    


Eat and Drink Fall-Flavored Everything 

In preparation for hibernation this winter, store up some tasty fall-inspired calories. Chicago’s home to every kind of cuisine imaginable, and autumn means Oktoberfest pulls out all the stops, all over town. Most neighborhoods have some kind of street fair or festival to celebrate, featuring brats, steins (or plastic cups) of beer, and music. 

Other fall-favorite foods to find in the city this season? A bowl of steaming ramen warms the soul like nothing else and, really, any kind of pie (why not pumpkin or apple) make chilly evenings a little warmer. Pour a dark beer, order your pumpkin spice latte, or sip some mulled wine with any dish this fall to channel the season. 

Wear your Bucketfeet, in autumn-themed designs, wherever your Chicago fall adventures take you. Grab a new pair decked out in fall florals or harvest hues to infuse your outfit with some fall fun. 


Shop Fall Bucketfeet Designs