Chicago is always a magical city, but the fall season takes that magic to a whole new level, with golden leaves, the crisp lake breeze and more fall-themed events than you can count in the Windy City. Between spooky cocktails and never-ending corn mazes, you’ll have no trouble staying busy this autumn. Keep reading for Connie Dornan's list of must-visit Chicago events happening this fall.
Jack’s Pumpkin Pop-Up
Experience the magic of Halloween in the city at Jack’s Pumpkin Pop-Up. Situated on two acres in Chicago’s Goose Island neighborhood, this charming pop-up offers a variety of fun activities for all ages, including pumpkin picking, axe throwing, and even exploring Chicago’s largest corn maze. There are carnival games, food trucks, fortune tellers, and countless photo opportunities as well. This fantastic fall destination is open until November 5.
Lincoln Park Zoo Fall Fest
Embrace the spirit of the season alongside some of your favorite animals at The Lincoln Park Zoo’s annual Fall Fest. Taking place on weekends until October 29, the Lincoln Park Zoo invites guests to enjoy live professional pumpkin carving, musical entertainment, story times, and of course, animal viewing. In addition to free programming, there are several ticketed experiences throughout the zoo including a Fun Slide, pumpkin patch pop-up, Harvest Maze, and inflatable attractions.
Nightmare on Clark Street
Image credit: Chicago Loop Alliance
Wrigleyville’s Deuce’s Major League Bar has transformed its bar and restaurant into three floors of fear and fun for its annual Nightmare on Clark Street pop-up. Brave souls can check out the multi-level, bone-chilling haunted house, or guests can enjoy music, drink specials and Insta-worthy Halloween décor in the main bar area. Nightmare on Clark Street is open through Halloween.
Arts in the Dark
Taking place on Saturday, October 21, Arts in the Dark transforms Chicago’s famous State Street in the loop into a mesmerizing display that showcases the local art community. As darkness falls, State Street will come alive with illuminated art, elaborate floats, costumed performers, and more, creating an immersive experience that celebrates the city’s commitment to the arts.
Never Trust The Living at The Dandy Crown
Image credit: Do 312
Every evening through October 31, The Dandy Crown in River West transforms from an eclectic lounge into “Never Trust The Living,” a ghoulish pop-up where guests can enjoy cocktails like Corpse Reviver No. 2, Blood & Sandworms and Widow’s Kiss. The interior and outdoor patio are covered in creepy Halloween decorations, creating the perfect setting for some fall photo-ops. Never Trust The Living has several frightful events planned for the month, including pumpkin carving, tarot card readings, and the Halloween Night Party.
JoJo’s Shake Bar Pumpkin Patch
Image credit: Secret Chicago
JoJo’s Shake Bar, renowned for its extravagant milkshakes and decadent deserts, has transformed its outdoor patio in Chicago’s River North neighborhood into a festive pumpkin patch. With hay bales, festive lights and an abundance of pumpkins, guests can enjoy the fall weather while indulging in pumpkin and apple pies, gourmet caramel apples, fall-inspired cocktails, and of course, their incredible shakes. Guests can also try their hand at crafting their own festive cocktails at one of their Basic Witch Mixology Classes or Pumpkin Succulent Workshops.
