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Chicago's Best Parties: Where to Spend Your Halloween Weekend in Chi-Town

Chicago’s Best Parties: Where to Spend Your Halloween Weekend in Chi-Town

  |     |   Chicago Activities, Holidays, Local Events

Whether you’re in search of a fright or want to bring your best costume ideas to life, Chicago has a ton of one-of-a-kind events to get you into the Halloween spirit. Just for starters, you can step inside a horror movie museum, play carnival games at an adult pumpkin patch, dance with drag queens at a costume ball, and so much more. Check out some of the top parties, booze cruises, and pop-up experiences for the 21-and-up crowd to start planning your Halloweekend itinerary in Chicago!

Jack’s Pumpkin Pop-Up on Goose Island

Visit a two-acre pumpkin patch in the heart of the city. Jack’s Pumpkin Pop-Up is a larger-than-life experience located on Goose Island. The massive outdoor experience has carnival games, axe throwing, three full-service bars, food trucks, fortune tellers, Chicago’s largest corn maze, and tons of photo opportunities. With a nighttime lights display and pumpkins galore, spend a crisp autumn evening outside at Jack’s. Open nightly this October. Tickets are available online for purchase. 

Haunted Halsted Halloween Parade

For those looking for both fun and fright, check out the Haunted Halsted Halloween Parade on Oct. 31 at 6 p.m. This costumes-encouraged event celebrates its 24th year along Halsted in the Northalsted neighborhood. Think your costume might turn heads? Enter one of the seven costume contest categories and win $500 for coming in first place. Complete with an award ceremony and an after-party, this crowd favorite event is sure to be a night to remember.

Rooftop Halloween Party and Drag Show 

Costume up and boogie down with the stars of RuPaul’s Drag Race at Marvin’s Food & Fuel in the West Loop. This special Haunt and Flaunt event on Oct. 28 is taking over the indoor restaurant and the climate-controlled rooftop. Admission includes a costume contest with prizes led by fabulous drag queens, premier DJs, a complimentary Halloween punch cocktail, and Halloween-themed movies projected on the big screen. Get your tickets today.

Halloween Murder Mystery Wine Dinner

Enjoy a classy evening of food, wine, and murder during this Halloween dinner party on Oct. 31 at Uvae Kitchen and Wine Bar in Andersonville. Guests will enjoy a five-course feast while trying to solve a mysterious murder. Costumes are encouraged, tickets are on sale now.

Gates of Hell Halloween at On Tour Brewing

For Halloween this year, On Tour Brewing Co. is hosting a Gates of Hell Halloween Weekend. From Oct. 28 – 31, the brewery will live stream the Las Vegas Halloween Phish shows starting at 9:30 p.m. each night. For a special Halloween-themed celebration on Oct. 30, On Tour’s musically themed costume contest will kick off with live music from blues-infused jam band Downers Groove. Wear your best for a chance to win an On Tour prize and bragging rights.

Slasher Museum Pop-up at Replay Lincoln Park

Replay Lincoln Park is back with another immersive pop-up experience. They’re transformed their arcade bar into a museum for the macabre, with eerie replicas from iconic slasher films, including Halloween, A Nightmare on Elm Street, and The Texas Chainsaw Massacre. From now through Oct. 31, guests can compete in Halloween trivia, horror-themed games, and more.

Fright Night at Momotaro

The Izakaya, Momotaro’s subterranean lounge designed to mimic the Japanese nightlife, is transforming into the abandoned Tokyo Metro station Oct. 29 – 30 and serving up some vintage Japanese horror, specialty cocktails, and delicious dishes to shock and delight. Tickets are available online and must be purchased in advance.

Sweet Dreams Halloween Pop-up at Rizzo’s Bar

Attend a horror movie-themed popup…if you dare. This October, Rizzo’s Bar & Inn is bringing your nightmares to life with a spooktacular indoor/outdoor Halloween pop-up. The bar will be decorated with epic Halloween scenes inspired by 20 classic horror movies, creating a massively twisted Halloween experience. The Sweet Dreams pop-up begins on Oct. 8 and will be open throughout the month. Tickets can be purchased online.

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