From now on, Chicago will become a picturesque display of autumn colors. The air is cool and crisp, the sun still warms the afternoons, and numerous fall festivities take place. Plus, Halloween is hiding around the corner.
From pumpkin picking and corn mazes to Halloween parties and haunted houses, these are the best things to do in Chicago in October!
Pop into Chicago’s largest pumpkin pop-up
With all of the things to do in Chicago in October comes pumpkin patches. Our pick of the bunch, and one of Chicago’s most popular Halloween time events, is most certainly Jack’s Pumpkin Pop-Up.
Now open for the season, this celebration of fall is one of Chicago’s most popular October events and also the only one that takes place 100% outside. This year, there will be a corn maze, axe throwing, carnival games, food trucks, full bars, and much more, all spread out over 2 acres on Goose Island!
Lose yourself in Richardson Farm’s ‘world’s largest corn maze’
While at Jack’s Pumpkin Pop-Up, you’ll find the largest corn maze in Chicago. You only need to travel a little outside of Chicago to enjoy the world’s largest corn maze. This year, the Richardson Adventure Farm theme pays tribute to John Deere, the man who invented the self-scouring steel plow, revolutionizing agriculture in the U.S. and around the world.
Open Thursdays through Sundays, Sept. 7—Oct. 27, the maze boasts 9-10 miles of trails as well as five maze games that vary in length and difficulty, including the farm scene investigation game, quiz questions, and finding all 24 hidden checkpoints.
Step into the Forbidden Forest
The Harry Potter: The Forbidden Forest Experience is finally open about an hour from Chicago! This luminous night walk takes you inside the Wizarding World and is filled with magical moments! Sip Butterbeer or hot chocolate under the stars, cast your Patronus and come face to face with a Hippogriff… just don’t forget to bow? Grab your tickets now. You can save 10% off during the weekdays in celebration of the Dark Arts season. New dates added due to popular demand…don’t miss the adventure! – Melissa Maynard
Lurk in the light of 1,000 jack-o-lanterns
This year, the Chicago Botanic Garden is going full Tim Burton with their Halloween event, Night of 1,000 Jack-O-Lanterns, for 10 spooky nights of October.
Even though you won’t be able to eat any of the pumpkins on display at Chicago Botanic Garden’s Night of 1,000 Jack O’Lanterns, you can still admire the brilliant intricateness of more than 1,000 hand-carved pumpkins — with some weighing up to 150 pounds! It’s one of the best things to do in Chicago in October!
Test your fortitude at one of Chicago’s haunted houses
Yes, there are a ton of haunted houses. However, one of our favorites and scariest is the 13th FloorHaunted House Chicago, which officially returns from the grave for its terrifying tenth season in Chicagoland. This year, set amongst forty thousand square feet of fun at Schiller Park, the Haunted House features two all-new, scary-as-hell exhibits: “Alien Autopsy” and “Lycans Curse.” With everything on this list, this haunted attraction might be one of the scariest things to do in Chicago in October.
Or Brave the Midwest’s only haunted house inside an actual abandoned prison
Head to this haunted house for those seeking more horror in their lives. Located just outside of Chicago, the Joliet Correctional Center, also known as Joliet Prison, awaits. The 13th Floor Haunted House Chicago team has transformed the prison into a horrifying haunted house experience.
If you’re intrigued by haunted places, enjoy exploring abandoned buildings, and want to do something different this Halloween, this experience is perfect for you. The first and only haunted house inside a real abandoned prison promises to be one of the spookiest Halloween experiences around.
Venture out to “Second Salem”
If you are intrigued by stories of supposedly haunted places, enjoy exploring abandoned buildings, and want to do something different this Halloween, consider visiting a real-life ghost town.
Just under two hours away is Whitewater, Wisconsin, nicknamed “Second Salem” due to its eerie tales of witchcraft. Check out https://secretchicago.com/whitewater-halloween-town-near-chicago/ to read more and decide if you’re up for the adventure.
Head to the Nightmare Bar in Chicago
Send your senses soaring with a Dining in the Dark experience
Dining in the Dark experiences offers a slightly less spooky yet unforgettable adventure. Elevate your date night or embark on a surreal experience with friends by sitting down for a blindfolded meal. It’s the perfect October activity to fully engage your taste buds as you indulge in a delicious three-course meal.
Have a Pumpkin Patch Shake at Jojo’s Shake Bar
Source/ Jojo’s Shake BarFamed for its over-the-top milkshakes and biggie hot chocolates, Jojo’s Shake Bar will once again elaborately deck out its adjacent patios in the heart of River North and Naperville with hay bales, hundreds of pumpkins, and some exceptional fall photo ops.
Visitors can feast on gourmet caramel apples, pumpkin and apple pies, spiked ciders, biggie hot chocolates, and, of course, their notorious shakes. If you’re a fan of those over-the-top milkshakes down at JoJo’s Shake bar, make sure you don’t miss out on their Famous Pumpkin Patch Shake. The one-month-only special comes topped with a pumpkin pie slice, a taffy apple, roasted marshmallows, and a toffee pretzel.
Grab a pumpkin at a pumpkin patch
One of our favorite places to visit is Jonamac’s Pumpkin Patch, which covers 12 acres. They offer a wide variety of pumpkins in different shapes and sizes, so you’re sure to find the perfect one for yourself or your family.
Play pickleball around Chicago
Pickleball in Chicago seems to be the hottest new sport; whether you want to play indoors or outdoors, we’ve garnered a list of the best places to play pickleball in Chicago—it’s one of the best things to do in Chicago in October if you want to get your heart racing!
Be captivated by a Candlelight Concert
Chicago’s sublime Candlelight Concert series provides an array of breathtaking spectacles. Talented musicians will be performing at extraordinary venues all over Chicago offering guests the chance to marvel at the enchanting combination of flickering candles and melodic sounds.
Stay in a Starved Rock Getaway cabin
Starved Rock State Park has a selection of minimalistic cabins with floor-to-ceiling windows, allowing guests to wake up fully immersed in the wilderness. Located in lush landscapes and with minimalistic yet comfortable designs, they offer the perfect escape for those wanting to disconnect from busy city lives with restorative stays in the middle of nature.
One of our state’s most impressive natural spectacles, Starved Rock offers over 13 miles of hiking trails, numerous cascading waterfalls, and 18 canyons.
Enter a Chicago museum for free
Free admission days are somewhat of a rarity during the summer months when Chicago’s tourism industry is thriving. Luckily, as we enter the fall months, many of our marvelous museums and attractions begin returning to frequent free admission days. This October in Chicago Shedd Aquarium, Field Museum, and the Museum of Science & Industry are all offering free midweek days.
Kick back at a revered brewery
Chicago is frequently recognized as one of the best beer cities in the country. With over 200 breweries, big and small, across Chicagoland, there are plenty of opportunities to enjoy finely crafted beer in different environments, whatever the weather. To ensure you’re visiting the best of the best, we’ve rounded up the best breweries in Chicago for you.
Go apple picking
While we’ll miss the blooming gardens and sunflower fields of summer, we’re excited for the changing leaves, pumpkin patches, and orchards to harvest the fruits of fall. The peak season for apple picking starts at the end of September and continues through October.
If you want to take measures into your own hands, head to our article on the best places to pick apples in Chicago to find out where to get your pick of the season’s best apple batch.
Go hiking near Chicago this fall
Every season offers new and different ways to enjoy nature, with spring splashing with the newly melted snow, summer peaking with an abundance of colors, fall trees bursting with warm red and golden hues, and winter bringing a clean slate of snow to remind us that the year has come to a close. No matter the time of year, there are plenty of great hiking spots near Chicago, but it is during the fall that many offer a particularly unique spectacle.
Head out of the city and see Illinois’ natural spectacles
Though our state may not boast wonders with the universal magnitude of the Grand Canyon nor the grandiose reputation of Niagara 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 natural wonders of Illinois that you can visit while they’re about to peak, so you can plan an outing regardless of whether you want to hike or not.
See the fall foliage
One of the best things to do in Chicago in October is, of course, to see the changing leaves. October marks the month that autumn hues sweep through the city, turning the parks from kelly green to crimson. The first thing to do is bask in this entrancing transition. We’ve picked out the best spots to view the changing leaves in Chicago for those who can’t get enough of the golden fall foliage, or just feel like doing a cannonball into a big ole pile of crackling leaves.