Autumn has officially arrived in Chicago, meaning all manner of fall-themed events and activities are about to pop up all over the city. It’s in fall that the city’s aesthetics undoubtedly peak as a hundred shades of autumnal color sweep through the streets of Chicago.
Pumpkins begin to populate the city, parks and riversides provide extraordinary displays of color ranging from crimson to canteloupe, and nearly all of Chicago’s bars, patios, museums and attractions of all kinds embrace the moment with Chicago fall activities across the city.
Of course, there is also Halloween awaiting around the corner and the many eerie experiences to be explored as October 31st draws closer.
We’ve here rounded up the best things to do in fall in Chicago whether you’re a seasoned local or an inquisitive tourist.
First and foremost, we have to address the astounding autumn aesthetics that sweep through Chicago this time of the year offering up prismatic picturesque views all over Chicago.
Whilst many of us will be looking over our shoulders melancholically at the passing of summer, the glass-half-full type of people will also be looking ahead at Chicago’s most beautiful months of the year as fall turns the city from green to crimson.
We’ve rounded up the best places to frolic in the fall foliage so you can make sure you’re getting the best out of fall, or just hunt down the best place to do a cannonball into a big ole pile of crackling leaves.
Of course, with fall comes a plethora of pumpkins in all shapes and sizes. While they can be carved and illuminated as Halloween draws closer, picking out the perfect pumpkin at the start of October is a ritual in its own right.
Many pumpkin patches in and around Chicago celebrate the start of fall with fresh produce, baked goods, cocktails, craft beer, rides, and photo opportunities making it the perfect Chicago fall activity for a family day out, group adventure, or even a wholesome date.
While decorating your own pumpkin and giving it the most creative features you can conjure is certainly a fun-filled activity, you’ll soon once again appreciate that pumpkin art is a lot more difficult than you remember.
At Chicago Botanic Garden’s Night of 1,000 Jack-O-Lanterns, you can admire the brilliant intricateness of more than 1,000 hand-carved pumpkins — with some weighing up to 150 pounds!
Carved by professionals, the many masterfully modeled pumpkins will include images of favorite Halloween characters, celebrities, and nods to Chicago all of which can be enjoyed for 10 spooky nights in October,
Of all Chicago’s fall activities and events, one of our favorites is most certainly Jack’s Pumpkin Pop-Up on Goose Island.
Now open for the season, this celebration of fall is one of the most popular in the city and also the only one that takes place 100% outside. This year there will once again be axe throwing, carnival games, food trucks, full bars, the city’s largest corn maze, and much more, all spread out over 2 acres in Goose Island!
While occupying a far smaller space, you’ll struggle to find anywhere offering fall-themed drinks and snacks as decadent as those found at JoJo’s Shake Bar.
Famous for its over-the-top milkshakes and biggie hot chocolates, Jojo’s Shake Bar has once again elaborately decked out its adjacent retro Western-themed patios in the heart of River North and Naperville with hay bales, hundreds of pumpkins, and some exceptional fall photo ops.
Guests can feast on gourmet caramel apples, pumpkin pies, and spiked ciders but of course, it’s their notorious shakes that people flock for. Don’t miss out on their famous fall-special Pumpkin Patch Shake and Cowboy Shake that have now returned to the menu.
The former comes topped with a toasted marshmallow, taffy apple, pumpkin pie, toffee pretzel, and a Pumpkin Graham Cracker.
While at Jack’s Pumpkin Pop-Up, you’ll find the largest corn maze in the Windy City, you only need to travel a little outside of Chicago itself to enjoy the largest corn maze in the world.
Richardson Farm in Spring Grove, Illinois, is home to a 28-acre labyrinth holding the title of the world’s largest corn maze, and this year it’s paying homage to none other than the terrifying dinosaurs of the Jurassic Park franchise.
As well as the 9-10 miles of maze trails, Richardson Farm is also home to a huge pumpkin patch where you can eat, carve, or smash giant pumpkins as well as throw them off of a giant 50-foot observation tower.
You’ll also find plenty of Halloween thrills this month in addition to a zip line, zorbing, a petting zoo, a giant slide, and much more to make sure your fall day out is filled with adventure!
The weather may be getting cooler, but the sun is still shining, which means it’s the perfect time for these fall activities in Chicago. Kick back at Chicago’s patios or beer gardens. Fall offers the perfect ingredients for a day sipping to your heart’s content while basking in the sun and enjoying the crisp autumn air.
There are plenty of patios and beer gardens (or biergartens) with live music, good food, and great drinks but we’ve rounded up our favorites to help you narrow it down!
While we’ll miss the blooming gardens, sunflower fields, and luscious green parks of summer, it’s time to look towards the orchards and places to harvest autumn fruits.
Apple picking is one of the particularly fruitful fall activities in Chicago and another wonderful thing to do with friends, family, or that romantic other half.
Though we’re aware that this isn’t strictly a central Chicago suggestion, sometimes the urban jungle can become too much and it is always a good idea to disconnect from busy city lives with restorative breaks to reconnect with nature, especially when Mother Nature puts on such an incredible show in the fall.
Though our state may not boast wonders with the universal magnitude of the Grand Canyon nor the grandiose reputation of Niagra Falls, Illinois is teeming with diverse ecological landscapes that transform into incredible spectacles this time of the year.
From monolithic marvels to cascading waterfalls, we’ve rounded up the 7 natural wonders of Illinois that you can visit while they’re about to peak.
One of these, Starved Rock State Park, has recently opened a selection of minimalistic cabins with floor-to-ceiling windows allowing guests to wake up fully immersed in the wilderness and the beauty of fall.
Amidst fall’s tide of orange comes the scariest night of the year. As October starts, the ghosts come out to play, cackling witches soar into the skies, and ghoulish creatures creep out from their lairs as Halloween in Chicago kicks off.
With the spooky season around the corner, it’s already time to start planning to hunt down all the Halloween thrills on offer, and luckily, we’ve rounded up some of the best Halloween events in Chicago that you shouldn’t miss this year!
[Featured image from Shutterstock]