Chicago in the fall? Chef’s kiss. The trees are showing off their colors, there’s a crispness in the air, and the city’s event calendar is stacked. Whether you're into spooky vibes, fall festivals, or getting your pumpkin fix, there’s something for everyone.
Here’s some of the events you definitely don’t want to miss this crispy season!
Arts in the Dark - October 19 @ 5:00 PM
Ready to kick off fall with a burst of creativity? Arts in the Dark is an evening parade where Chicago’s art scene takes over State Street. You’ll see larger-than-life puppets, glowing costumes, and wild performances.
The best part? The parade celebrates the city’s diverse cultures and communities, so it’s like getting a little taste of every part of Chicago. Grab your crew and enjoy the artistic magic!
Open House Chicago - October 19-20
Feel like being nosy but, like, in a cool way? Open House Chicago gives you behind-the-scenes access to some of the city's most iconic buildings. We're talking skyscrapers, theaters, historic homes—places you’ve walked by and thought, “I wonder what it looks like inside?”
Now’s your chance to find out! Whether you’re a history buff or just love a good Insta backdrop, this one’s for you.
Adults Night Out: Howl-o-ween at Lincoln Park Zoo - October 24 @ 6:30 – 10:00 PM
Spooky season meets happy hour at the zoo, and yes, it’s as fun as it sounds. Adults Night Out: Howl-o-ween lets you wander through the zoo after hours with no kids in sight. Sip on craft cocktails, try some tasty bites, and keep an eye out for some of the zoo’s nocturnal animals (not to mention, killer costumes).
Dress to impress and get ready for a wild night!
Maxwell Street Market - October 27 @ 9:00 AM – 2:00 PM
Want to switch up your fall weekend routine? Hit up the Maxwell Street Market on October 27. It’s a Chicago classic with a mix of vintage finds, unique art, and the best tacos in town (yes, this is your sign to treat yourself).
If you’ve been meaning to score some funky antiques or just want to soak up some local culture, this is the spot.
Haunted Halsted Halloween Parade - October 31 @ 6:30 - 10:00 PM
This isn’t your average Halloween parade—Haunted Halsted goes all out. On Halloween night, Halsted Street turns into a runway for some of the wildest, most creative costumes you’ve ever seen. The whole neighborhood comes alive with lights, music, and spooky energy.
Whether you're dressed up or just there to watch, this is a must-see event.
Jack’s Pumpkin Pop-Up - Now through November 3
If your fall bucket list includes picking pumpkins, getting lost in a corn maze, and taking more Insta pics than you care to admit, Jack’s Pumpkin Pop-Up is calling your name. It's like a mini fall wonderland in the heart of the city.
Plus, there’s a bar (because, priorities) and photo ops around every corner. The perfect fall day, hands down.
Your Fall Adventure Awaits
With so many fall festivities happening around Chicago, there’s no excuse not to get out there and enjoy the season! Whether you’re carving pumpkins, getting your culture fix at Open House, or showing off your best Halloween costume, Coast at Lakeshore East puts you in the middle of all the action.
Grab your sweater, hit the city, and make the most of this magical time of year! 🍂🎃