Spooky Things to Do in Chicago for Halloween
Chicago takes Halloween seriously. Between haunted history tours, a hotel with a reputation for restless guests, pumpkin-lit parades, and family-friendly frights all over the city, there’s no shortage of things to do downtown this fall. If you’re out and about during daylight hours, too, it’s also peak season for Chicago’s best fall colors, so it’s easy to pair a little leaf-peeping with your spooky season plans. And if you want a scare with a view, there’s one dare in town that has nothing to do with ghosts: standing on 1.5 inches of glass, 1,353 feet above the Loop, at Skydeck Chicago.
The best spooky things to do in Chicago for Halloween include ghost and haunted history tours, the famously “haunted” Congress Plaza Hotel, Halloween parades and pop-ups around the city, family-friendly zoo and pier events, and the genuinely heart-stopping view from at The Ledge, 103 stories up at Skydeck Chicago.
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Ghost Tours & Haunted History
Chicago’s history includes plenty of dark chapters, and a handful of tour operators around the city make a business out of walking visitors through them, from Prohibition-era gangster history to sites tied to the city’s more unsettling folklore. If you want your Halloween with a side of local history, a haunted history or ghost tour is an easy way to spend an evening downtown. Availability and routes vary by operator, so check current schedules before booking.
Haunted Hotels
No Chicago Halloween list is complete without the Congress Plaza Hotel, widely described as one of the most haunted hotels in the country. Whether or not you believe the stories, the hotel plays into its reputation each year with Halloween-season events, making it a popular stop for anyone chasing a good scare downtown.
Halloween Parades & Pop-Ups
Chicago’s Halloween calendar fills up fast every October. Arts in the Dark brings an artist-led nighttime parade with giant puppets and lanterns through downtown, the Northalsted Halloween Parade draws elaborate costumes to Boystown, and seasonal pop-ups like Jack’s Pumpkin Pop-Up turn empty lots into corn mazes and pumpkin patches for the month.
Family-Friendly Halloween Fun
Not every Chicago Halloween outing needs to be scary. Lincoln Park Zoo and Navy Pier both typically run family-friendly Halloween programming each fall, with costumed trick-or-treating, daytime activities, and events built for younger visitors rather than frights. As with the parades above, confirm current-year dates and details before you go.
A Different Kind of Scary: Frightful Heights at Skydeck
If ghost stories aren’t really your thing, Skydeck Chicago offers a different kind of Halloween dare, one with zero hauntings and considerably better views. We’re not claiming Willis Tower is haunted. What we can promise is that stepping onto The Ledge, a glass balcony extending 4.3 feet outside the building on the 103rd floor, 1,353 feet above the street, will get your heart racing all on its own.
Consider it a frightfully good time: no ghouls required, just a floor made of glass and a view that makes your stomach drop in the best way. It’s the kind of scare you can brag about afterward, and unlike a haunted house, nobody’s going to jump out at you.
Before or after your dare, warm up with a walk through the Chicago Museum, included with your visit, or make a full night of it with dinner and a view. Just don’t blame us if your palms sweat a little on the way out.
Think you can handle it? The Ledge doesn’t require a costume, just a little nerve. Book your timed entry now and see for yourself why our glass floor 103 stories up is scarier than anything else on your list of things to do in Chicago this Halloween.
FAQs About Halloween in Chicago
What are the best spooky things to do in Chicago for Halloween?
Chicago’s Halloween season includes ghost and haunted history tours, the famously haunted Congress Plaza Hotel, Halloween parades and pop-ups, family-friendly zoo and pier events, and a stop at The Ledge at Skydeck Chicago for a height-based scare with none of the ghosts.
Is Chicago good for Halloween?
Yes. Chicago has a full calendar of Halloween-season events, from haunted history tours and costume parades to family-friendly activities and pumpkin patches around the city.
Is Skydeck Chicago scary?
Skydeck isn’t haunted, but The Ledge, a glass balcony extending 4.3 feet outside the building on the 103rd floor, gives visitors a genuine height-based thrill. It’s a different kind of scary, more heart-pounding dare than ghost story.
Is Skydeck a good Halloween activity for families?
Yes. Skydeck is family-friendly year-round, including during Halloween season, with The Ledge and the Chicago Museum offering an exciting outing without any horror themes involved.
What is the most haunted hotel in Chicago?
The Congress Plaza Hotel is widely regarded as one of the most haunted hotels in Chicago and frequently appears on national lists of haunted hotels.
Are there Halloween parades in Chicago?
Yes. Chicago hosts several annual Halloween parades and events, including Arts in the Dark and the Northalsted Halloween Parade. Dates vary each year, so check with event organizers for current schedules.