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.
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 for Halloween.
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 from September to October, 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.
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 in October, 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.
Every weekend through October, 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 is 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
JoJo’s Shake Bar, renowned for its extravagant milkshakes and decadent desserts, 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-themed 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.
For parents with kids who prefer to celebrate at home, you can find below plenty of creative and festive activities to keep the Halloween spirit alive. Whether you’re looking to attend a local event or plan a cozy night of spooky fun indoors, this guide has everything you need to make the most of Halloween in Chicago.
Deliver Goody Bags
If it’s not possible to go out trick or treating, organize a goody bag drop-off with your friends and neighbors. Everyone can put their own twist on their bags and showcase their personality using a special theme or favorite candy. Be sure to only include wrapped candies to prevent any contamination, and follow social distancing guidelines when it’s time to drop off your baggies.
For those who are not able to go out for any reason, consider organizing a car parade with your friends and neighbors. Put on your best costume, decorate your car with Halloween-themed lights and decor, and take to the streets for a fun-filled Halloween parade.
Zoom has become a trusted source for safe gatherings since 2020. Download a Halloween-themed background, don your favorite costume, and join your pals online for an evening of scary stories and games. You can also have a virtual Halloween cocktail or treats decorating contest, and see who has carved the best jack-o-lantern.
Scavenger hunts are a favorite past time, and we think it can be a fun way to celebrate this holiday too. In the spirit of the season, plan a Halloween-inspired adventure. On-theme ideas include finding a pumpkin, a skeleton, a bat, and a jack-o-lantern. If you are less comfortable with a neighborhood-wide scavenger hunt, set one up inside the various rooms of your home and get creative with your riddles and clues. You can even add candy into the mix! Whether you choose to explore the haunted streets of Chicago in one of its many Halloween-themed events or enjoy a cozy night of Halloween fun at home, there are endless ways to make this holiday memorable. From spooky events and parades to DIY crafts and themed movie marathons, families can enjoy a mix of excitement and creativity. No matter where or how you celebrate, the most important part is creating lasting memories with your loved ones. So, whether you’re venturing out or staying in, Chicago offers plenty of opportunities to make this Halloween truly special!
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