As the weather chills and the leaves begin to change, Chicago says goodbye to another summer and welcomes in the autumn. While there are tons of activities to enjoy this fall, no holiday captures the seasonal spirit quite like Halloween, and this year, whether you're looking for family-friendly adventures or a boozy night out, the city has never had so many options to choose from.
So throw on your costume because there's never been a better time to venture out for the holiday and experience all the boos, brews, and spooks the city has to offer.
Jack’s Pumpkin Pop-Up
One of the biggest and most popular pop-ups for the Halloween season returns for its ninth year with even more activities and entertainment. Featuring the city’s largest corn maze, a pumpkin patch, carnival games, axe throwing, and more, Jack’s offers a little something for everyone. The event runs through Sunday, Nov. 1 and is open to all ages. Tickets are required for entry, with prices varying based on your desired package.
Website: Jack's Pumpkin Pop-Up
Nightmare on Clark Street
Turn up the fear factor at this festive Halloween function located at Wrigleyville's Stolen Saddle. Guests embark on a top-notch walk-through haunted house before enjoying themed cocktails and snapping photo ops atop the bar's spectacular rooftop. The event is 21+ and runs through the end of the weekend, with every ticket coming complete with a free drink.
Website: Nightmare on Clark St.
Subscribe to Chicago Star’s Weekly City Buzz Newsletter
Never Trust the Living
If you're looking to sip your way through spooky season, look no further than Never Trust the Living. This seasonal pop-up returns for its fourth year at one of River West’s best cocktail lounges, Dandy Crown. Featuring devilishly delicious holiday cocktails, fan favorites include the Kettle Corn Old-Fashioned (popcorn-infused bourbon, salted demerara, vanilla bitters, orange), the Poison Apple (green apple gin, dry vermouth, pickled Granny Smith brine, lime), and the Scarecrow (reposado tequila, roasted sweet potato, piloncillo, ancho chile, lime) among many others. The bar is decked to the nines with Halloween decor and also offers a pet-friendly, heated, outdoor patio.
Website: Never Trust the Living
Black Lagoon
With 39 locations across the country this year, the Black Lagoon is one of the biggest pop-up experiences around. Chicago’s event will take place at the moody British pub, Albion Manor, in the bars upstairs event space “The Parlour.” Known for a curated, themed cocktail selection, heavy-metal music, and goth aesthetic overtones, the Black Lagoon is the perfect opportunity to get into the macabre musings of the holiday. Costumes are encouraged, and no tickets are required for entry; however, the establishment does recommend making reservations ahead of time as large crowds are typically expected.
Website: Black Lagoon
Read more on Chicago Star:
Salem House
Inspired by the cult classic “Hocus Pocus” Halloween movie, Salem House is a lively holiday activation taking place at the trendy River North social hub Tree House. The spacious venue features playful seasonal menu creations, photo installations, and immersive decor. The event is open for brunch and continues well into the night, meaning it's always a good time to stop by and step into this storybook celebration. The pop-up will run through Thursday, Nov. 12, at which time the bar will transition into its Christmas-themed experience, “Santa's Social Club.”
Website: Salem House at Tree House






(0) comments
Welcome to the discussion.
Log In
Keep it Clean. Please avoid obscene, vulgar, lewd, racist or sexually-oriented language.
PLEASE TURN OFF YOUR CAPS LOCK.
Don't Threaten. Threats of harming another person will not be tolerated.
Be Truthful. Don't knowingly lie about anyone or anything.
Be Nice. No racism, sexism or any sort of -ism that is degrading to another person.
Be Proactive. Use the 'Report' link on each comment to let us know of abusive posts.
Share with Us. We'd love to hear eyewitness accounts, the history behind an article.