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Halloween won’t fall on a Saturday for another 11 years, so here at Time Out Chicago, we’re going all out. Even better? We get an extra hour of Halloweekend when the clocks fall back on Sunday, November 1. Naturally, we’re going to make every minute count.
Over the past few weeks, our team has been experiencing and curating guides on where to party, drink and be spooked on Halloween in Chicago. Some of our favorite things we’ve done this year include First Lady’s Creepy Cruise, which is equal parts ghost tour and architecture tour, and Second City’s hilarious Halloween-themed improv show Travel Can Be Murder.
Whether you’re looking to party in your Elizabeth Holmes or Freaky Nikki costume, or you’re throwing on cat ears (once again) to take your kids trick-or-treating around the neighborhood, we’ve got your Halloween plans covered. Staying in? Queue up a scary movie marathon with the best horror movies of the year, or test your limits by watching one of the scariest movies of all time (according to science).
RECOMMENDED: The best Halloween bars and parties in Chicago
No matter what your plans are, there’s no excuse not to get in the spooky spirit this Halloweekend. Read on to discover the best things to do over Halloween weekend in Chicago.
1. Haunted Halsted Halloween Fest & Parade
Wanna see some of the best Halloween costumes in the city? Head to Northalsted, where hundreds of people show off their creations at this spooky festival and procession. During the day, a street fest features food, drinks, live entertainment and more. At 7pm, you'll find drag queens, kids, parents and pets marching in the 30th annual Halsted Halloween Night Parade, which typically features impressive group costumes and dancers performing all the moves to Michael Jackson's "Thriller." Stick around afterwards for the costume contest awards ceremony.
2. 'Travel Can Be Murder'
The Second City is reviving its annual Halloween series for a third time with Travel Can Be Murder, a 90-minute, unscripted whodunit inspired by Murder on the Orient Express and Death on the Nile. The show begins with an audience suggestion for what mode of transportation the performers will be travelling on. At the show I attended, it was a zeppelin. The next hour and a half was filled with an elaborate improvised storyline featuring kooky characters, witty dialogue and impressive off-the-cuff improvisation that ended with a death-by-helium ingestion.
3. Arts in the Dark Upside Down Parade
In addition to the regular Arts in the Dark parade on State Street, the arts organization LUMA8 is hosting a "reverse" parade—in which attendees pass through a stretch of costumed performance groups lining Russell Drive in Washington Park. Bonus: At the end of the route, attendees will get a complimentary candy bag and other goodies. Come wearing your best Halloween costume!
4. 'Rocky Horror Picture Show' at Music Box Theatre
The Music Box Theater brings back its beloved annual Halloween tradition with five screenings of The Rocky Horror Picture Show. Each screening is paired with a shadowcast as actors perform in front of the screen during the film. It's a wonderfully weird tradition that's known to sell out.
5. Chicago Seadog Haunted River Tour
Chicago Seadog, part of City Cruises Chicago, offers a spooky ride down the river and lake this season with its Haunted Tours. The 75-minute tours, offered on Fridays, Saturdays and Sundays through October, are moderated by a costumed guide, who shares the eerie history of supernatural occurrences in Chicago. Guests (and their dogs!) are encouraged to come in costume and BYOB if they want to get boo-zy on board.
6. Nightmare on Clark Street
Hosted at Stolen Saddle—one of Chicago's largest country bars—this annual Halloween-themed extravaganza features photo ops galore, plus an upstairs bar serving spooky cocktails like Freddy’s Tequila and Darcula's Blood. There’s no haunted house this go-around—but that doesn't mean Nightmare on Clark Street won't be serving up scares this Halloween season.
7. Haunted House Party at the Shedd
The Haunted House Party is back at the Shedd Aquarium, bringing together house music and Halloween for a spooky night to remember. Despite the event's name, there will be no scares here—the event's vibe is decidedly more "house party" than "haunted." Guests aged 21 and up are invited to come dressed in their finest costumes and dance the night away to sets by DJ Gent Hunt and DJ Heather.
8. Haunted Halloween Ball
The Congress Plaza Hotel hosts its annual Haunted Halloween Ball, inviting costumed attendees, aged 21 and up, to spend a night dancing and celebrating in a building that some claim is haunted. Guests will be able to mingle with spirits and the not-yet-deceased in the hotel's ballrooms, which sport spooky decorations, zombie cocktail servers, go-go dancers and vampire bellmen. You'll have access to multiple bars, views of the skyline and the chance to enter a costume contest and compete for $2,000 in cash and prizes.
9. Creepy Cruise
Explore Chicago's eerie past as you snake down the river aboard the First Lady's Creepy Cruise. The 90-minute tour, which frequently sells out, combines architectural history with stories of the city's shady past, from mob legends to ghost sightings, for a spooky evening on the water.
10. Sanctum Dark Music Festival
Sanctum returns for another weekend of dark music, dancing and community at Thalia Hall and its piano lounge, Tack Room, this Halloweekend. Sanctum prides itself on standing head and shoulders above other music festivals, bringing in extra sound support from Big Audio, decking the room with curated decor and offering an “ALL VIP” ticketing concept that grants all attendees the same level of access. This year's lineup includes A Split Second, Buzz Kill, Pink Stiletto, Grave Love and more, plus a VHS Dungeon Room, photo booths, vendors and more.
11. Streeterville Doggy & Kitty Halloween Party
Chicago's most adorable Halloween party happens every year at the MCA Sculpture Garden, where local dog and cat owners bring their costumed pets for a parade around the premises. The best-dressed furry friend—chosen by Alderman Brian Hopkins and Streeterville resident Maureen Schulman—will receive prizes. Donations support the dogs, cats, kittens and puppies residing at PAWS Chicago.
12. Montrose Monster Mash
Families are invited to trick-or-treat along Montrose Avenue on Halloween Eve for the annual Montrose Monster Mash. Along the way, local shops and restaurants will hand out candy for a spirited night of spooky fun. There's no cost to join, but attendees are encouraged to register online in advance. Don't forget your costume!
13. Drunk Dracula
The team behind the irreverent long-running comedy show Drunk Shakespeare is unleashing their latest monster mash-up, Drunk Dracula, on the city during the month of October. The premise is simple, but no less hilarious: Dracula gets drunk, unsuspecting citizens fight for survival and Bram Stoker’s vampire classic gets a boozy makeover that’s equal parts unhinged and fun.