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A Spooktacular City: The Best Things to Do in Chicago for Halloween

A Spooktacular City: The Best Things to Do in Chicago for Halloween

  |     |   Holidays, Local Events

Celebrate Halloween in Chicago with these spooky, spectacular, and supernatural events. The city is packed with haunted happenings each October, from frightening to friendly. Celebrate the spookiest time of year with nighttime parades, haunted houses, spooky movies, ghost tours, pumpkin picking, and beyond. Here are a few of the best things to do for Halloween in Chicago.

See a nighttime arts parade

Arts in the Dark, a beloved annual event each October, celebrates the artistic side of Halloween. This enchanted nighttime parade features large-scale puppets, costumed performers, elaborate floats, and luminous lanterns. The city’s creative community, including renowned institutions like the Art Institute of Chicago and Lookingglass Theatre Company, combine forces to create this surreal evening in downtown Chicago.

This year, the Arts in the Dark parade will take over State Street between Lake and Van Buren on Saturday, Oct. 30 from 6 – 8 p.m. This year will also feature an Upside Down Arts in the Dark event (a “reverse” parade with more than 20 performance groups in Washington Park, where costumed families can walk through the route) on Saturday, Oct. 23 from 12 – 3 p.m.

Experience Night of 1,000 Jack-o’-Lanterns

This popular event lights up the night with hundreds of intricately hand-carved pumpkins. During Night of 1,000 Jack-o’-Lanterns at the Chicago Botanic Garden, visitors can wander the gorgeous grounds at night and admire the impressive jack-o’-lanterns, each handcrafted for hours by expert artists. There will also be plenty of fall snacks and sips, like spiked cider and seasonal beer.

This year’s event will take place Oct. 13 – 17 and 20 – 24, 2021. Tickets go on sale to the public on Aug. 27.

Party at the Northalsted Halloween Parade

The Northalsted Halloween Parade, ranked one of the 10 Best Halloween Celebrations in the U.S. by Fodor’s Travel, is held in the heart of the Northalsted (also known as Boystown) neighborhood. The raucous procession kicks off on Sunday, Oct. 31 at 7:30 p.m. on Halsted Street at Belmont Avenue with the Chicago Thriller flash mob, a troupe of ghoulish zombies performing the famous dance routine. Join in the dancing or follow the parade route north, where a panel of drag queens will award prizes for the best costumes.

Take a haunted tour of Chicago

Congress Plaza Hotel, Lincoln Park Zoo, the former site of H.H. Holmes’ Murder Castle — these are just a few of most (allegedly) haunted sites in Chicago. Decide for yourself on these haunted and ghost tours of the city:

Explore our full guide to haunted Chicago tours. Or create your own DIY walking tour with our list of Chicago’s most haunted places.

Celebrate Day of the Dead

Day of the Dead may coincide with Halloween, but the beloved Mexican holiday is a one-of-a-kind celebration. The National Museum of Mexican Art is the perfect place to experience it, with an annual exhibit dedicated to Day of the Dead customs and traditions. The exhibit, Día de Muertos – A Time to Grieve & Remember, will run from Sept. 10 to Dec. 12, 2021.

They’ll also be hosting their annual Día de Los Muertos: Love Never Dies Ball on Saturday, Nov. 6, 2021. Enjoy an evening of cocktail-making, live music, face painting, and more.

Catch a scary movie

Movie marathons, outdoor movie theatres, and drive-in movies are popping up all around Chicago, and you can expect plenty of spooky screenings this Halloween season.

  • The Music Box of Horrors is back on Saturday, Oct. 23, 2021, with 24 hours of horror movie madness at the historic Music Box Theatre. Get your tickets now for horror classics, cult favorites, and so-bad-it’s-good flicks.

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