Chicago’s Coolest Halloween Parties and Events This Month

The only frightening thing this Halloween would be missing any of these amazing events.

It’s finally, mercifully, time. The leaves are changing and crunching satisfyingly underfoot, socks and slides are being replaced with Doc Martens, and the streets are once again lined with cozy mustard-yellow cable-knit sweaters. And no stretch of fall has more fun things to do than right now: Halloween. There's so much to eat, so many ways to feel vaguely spooked or mortally terrified, and so many festive excuses to drink and drink and drink around town. Here are all the best ways for you—and the skeleton living just underneath your skin—to make the most of Spooky Season in Chicago.

Lincoln Hall + Schubas
Lincoln Hall + Schubas

Friday, October 29
Schubas
Hopefully Schubas has enough White Russians on hand for this Big Lebowski-themed party, featuring live music from Zoofunkyou playing songs from the movie as well as original jams. There’s also a costume contest showcasing God-only-knows how many bearded dudes in robes.
Cost: Tickets start at $12 per person

Saturday, October 31
Boards at DuSable Harbor
Is there any holiday that doesn’t call for a booze cruise? If there is, it sure ain’t Halloween. Board the festive Anita Dee II Yacht at DuSable Harbor and set out to sea (okay, out to lake) for a fun-filled night of cocktails, dancing, massive skyline views, and maybe a new friend or two.
Cost: Tickets start at $20 per person

LUMA8
LUMA8

Saturday, October 30
State Street between Lake and Van Buren
One of the best nights of the year returns to downtown as Arts in the Dark makes its way down State Street with all manner of weird floats, giant puppets, and oddball creative performances that will totally freak you out—in a good way.
Cost: Admission is free

Virgin Hotels Chicago
Virgin Hotels Chicago

Saturday, October 30
Virgin Hotels Chicago
Bearded ladies. Contortionists. Fire breathers. Go-go dancers. Trampoline aerialists. Yep, the freaks are coming out for this hip hotel rooftop shindig at Virgin’s Cerise. Enjoy the spectacle with the help of marshmallow popcorn balls, cotton candy, and other sweets, plus specialty cocktails and more.
Cost: Tickets run $30 per person; additional menu prices vary

Saturday, October 30
Congress Plaza Hotel
The Congress Plaza isn’t just the place to get drinks and hide out from the crowds after Lolla. It’s also the place for Chicago’s biggest Halloween bash with the hotel’s massive 20,000-square-foot ballrooms decked out in nightmarish décor with DJs, zombie cocktail servers dressed as French maids, go-go dancers and more.
Cost: $20-$1,000

The Den Theatre
The Den Theatre

Saturday, October 30 - Sunday, October 31
The Den Theater
Burlesque and drag performers help bring the Rocky Horror Picture Show to life at this risque immersive experience complete with live DJs, pole dancing, a vendor fair, flash tattoos, a vintage Polaroid booth, and a costume party.
Cost: Tickets start at $76 per person

Punch Bowl Social
Punch Bowl Social

Saturday, October 30
Punch Bowl Social
Halloween jams and a costume contest set the stage for this spooky day party with a special Halloween punch that should get you in the mood to boogie—and/or play games like giant Scrabble, ping pong, and foosball.
Cost: No cover; menu prices vary

Saturday, October 30
Epiphany Center for the Arts
Looking to party in a renovated church this Halloween? Look no further than this epic throwdown at Epiphany Center for the Arts with live music in three different venues. Choose your musical adventure with Afro house music, live blues, or a Michael Jackson Thriller dance party complete with a costume contest and specialty cocktails.
Cost: Tickets start at $20 per person

LiqrBox
LiqrBox

Saturday, October 30
Various River North bars
For those among us who deem bar crawls “essential,” there’s this River North crawl hitting up spots like Joy District, Hubbard Inn, LiqrBox, and more with themed drinks, a costume contest, DJs, and a digital bar map.
Cost: Tickets run $30 per person; additional menu prices vary

Northalsted
Northalsted

Sunday, October 31
Halsted from Aldine to Waveland
Bust out your finest costume for this all-sensory spectacle making its way down Halsted in Boystown with a Grand Marshals-led Halloween parade and afterparty featuring not one—but six—costume contests, plus a live performance from all-female cover act Catfight.
Cost: Free

Jack's Pumpkin Pop Up
Jack's Pumpkin Pop Up

Now through Sunday, October 31
1465 N. Elston
It’s kind of weird to call this a pop-up when Jack’s Pumpkin Pop-Up has taken over almost the entirety of Goose Island, but here we are. Nomenclature aside, Jack’s Pumpkin Pop-Up’s sheer size means that it mimics the feel of a rural harvest festival smack dab in the heart of the city. Attractions include plenty of Instagram-worthy photo backdrops, apple cider donuts, take-home pumpkins, Chicago’s largest corn maze, three full bars, axe-throwing, and axe-throwing. I know we mentioned axe-throwing twice, but trust me, you’ll be thanking us for reminding you to get your practice in when you’re staring down a hockey mask-wearing murderer wielding a machete.
Cost: Tickets start at $30 per person

Navy Pier
Navy Pier

Now through Sunday, October 31
Navy Pier
The holiday lights at Navy Pier get a lot of press (and for good reason), but don’t sleep on their Halloween-themed Pier Pumpkin Lights display. Somehow still flying under the radar, Navy Pier is once again transforming into an Insta-friendly seasonal spectacle with nearly 1,000 pumpkins on display plus a variety of pop-up installations and specials throughout Navy Pier.
Cost: No cover; additional costs vary

Thursday, October 28
Lincoln Park Zoo
The Great Pumpkin Glow is a Chicago Halloween mainstay for a reason. Dotting the zoo with cash bars, pumpkin patches, and corn mazes, while at the same time barring all those loud, meddling kids from entry turns the best zoo in America into a beautiful fall refuge. There's also a live DJ, haunted trail, lawn games, and even animal chats if you’re so inclined.
Cost: Tickets start at $15 per person

Gallagher Way Chicago
Gallagher Way Chicago

Thursday, October 28
Gallagher Way
For the fourth year in a row, Gallagher Way is hosting a huge, family-friendly party right outside Wrigley Field. The Pumpkin Party brings tons of fall-themed fun to Gallagher Way, including candy stations, lawn games, spiked hot chocolate for the grownups, balloon animal artisans, and even a roving magician. This culminates in an evening screening of Hotel Transylvania on the enormous screen that normally shows the Cubs’ live feed. It might not take the sting off of the Cubs finishing fourth in the NL Central, but it’ll ease the misery just a touch.
Cost: Admission is free; additional costs vary

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Jay Gentile is a contributor for Thrillist.
Sam Greszes is a contributor for Thrillist.