Chicago

Chicago's Coolest Halloween Parties and Events This Month

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

LUMA8
LUMA8
LUMA8

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
Lincoln Hall + Schubas

A Lebowski Halloween

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

Haunted Halloween Night Cruise

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
LUMA8

Arts in the Dark

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
Virgin Hotels Chicago

Freakshow

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

Haunted Halloween Ball

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 d√©cor with DJs, zombie cocktail servers dressed as French maids, go-go dancers and more.
Cost: $20-$1,000

The Den Theatre
The Den Theatre
The Den Theatre

Science Fiction Double Feature: An Immersive Rocky Horror Picture Party

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
Punch Bowl Social

Punch Bowl Social Halloween Fest

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

Epiphany’s 1st Annual Halloween Extravaganza

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
LiqrBox

Official Halloween Bar Crawl

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
Northalsted

Haunted Halsted Halloween Parade & Costume Contest

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
Jack’s Pumpkin Pop Up

Jack’s Pumpkin

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
Navy Pier

Pier Pumpkin Lights

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

Adults Night Out: The Great Pumpkin Glow

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
Gallagher Way Chicago

Pumpkin Party

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.

Chicago

Robyn DaCultyre Is Doing It for the Culture

"The cool thing about Ohio is that there is literally a place for everyone."

Photo by Kayode Omoyosi
Photo by Kayode Omoyosi
Photo by Kayode Omoyosi

I was introduced to Robyn DaCultyre at an Untitled Queen show at C’mon Everybody in late January, and it was one of the most unique drag shows I’d seen in a while. Afterwards, I tracked down this self-described “drag creature” and video chatted about her drag origin story, the state of drag in her native Ohio, and the dual identities that make up her persona. Thrillist: I want to ask you about how Robyn DaCultyre came about and your point of view behind your performance.

Robyn DaCultyre: I’ve been travelling around the country from a young age in ministry and Christian studies. I moved to Chicago right after high school. Four years later, moved back to Columbus and decided I didn’t really want to do church anymore; that wasn’t where my heart was.

I had a really low point in my life and had a suicide attempt and then really found drag and started doing drag as a coping mechanism and way to let off steam. I started in July of 2019, and it was really a lot of punk and metal music. I created this drag creature of sorts and they were really out of this world and celestial and all of those fun alien type terms.

And then we went into a global pandemic and I had a lot of time to figure out who I wanted to be. Digitally I was still doing a lot of drag creature-esque numbers and all of that, but I had this moment where we’re on the front lines getting hit with pepper spray and rubber bullets and pepper spray-all of those lovely things. And I said, I have this platform and I need to start showcasing what’s happening.

Untitled [Queen] stepped in at the right time and messaged me and said, “I’m doing this show for Independence Day called Untitled in America with 52 different performers and I want you to be a part of it.” It was at that moment I was able to take the footage I had been recording on the front lines and incorporate it into digital content. I did a song called Black Like Me by Mickey Guyton that talks about white picket fences, but if you want to see how America is, then you should try being Black like me. The imagery of what’s literally happening in Columbus in that digital performance really spearheaded me into focusing on people who look like me.

Nina Simone is one of my biggest inspirations, and one of her quotes that resonates with me is that it’s the duty of the artist to resonate with the times. My art is politically charged. I like to entertain, but there will definitely be a time when you come to a show expecting to have your drink and be chill and that might not be the case.

How did the name Robyn DaCultyre come about?

I was smoking with Ursula Major, who was on season one of Dragula, and the first time I introduced myself to her I was Robyn Banks, which is my drag name originally. She said, “Well, do you just not want to be original at all?” [Laughs] And I sat with that for a couple of months, and I got really stoned one day and was listening to Janelle Monae, and she talks about doing it for the culture, and I said “I do it for the culture, too!” And the rest is history.

And you started a series called Melanated.

We started Melanated last February. I told the idea to my show director that there were no shows specifically run by Black people that only featured Black entertainers. I wanted to do this show for a night and she said, Why don’t we do it once a week for the whole month? The first show happens, and it’s a sold out crowd, and [my director] comes back and says we should do this every month. So I sucked it up and here we are a year later.

Melanated is the only fully Black show in all of the state. It’s a horrible marketing tool and not something I want to promote, but it is just a fact. It amazes me that we are the 13th largest city in America and there’s nothing here that’s fully focused on Black entertainers. The name also comes from Janelle Monae; she says she’s highly melanated and I said, that works.

Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)
Photos by Chay Creates LLC (left) and Bridget Caswell (right)

You refer to yourself as a drag creature, as opposed to drag queen or king…

This is actually the first time I’m making this public. I am in this place where I want to separate the alternative creature from who this melanated goddess or whatever is. DaCultyre is definitely the person who runs Melanated and then Robyn is this drag creature that is out of this world and really loves punk and alternative music. And both intertwine to make Robyn DaCultyre.

You also do pageants. Tell me about that.

In 2020 I was appointed by Nina West, who is from Columbus, as the representative from Ohio for National Entertainer of the Year in Louisville, Kentucky. I placed ninth out of 13 contestants and I really fell in love with the system and fell in love with the pageantry and loved the idea of reigning and being different. I want to show that we as alternative performers, as bearded performers, you can come into these systems and shake things up.

Is there a uniquely “Ohio” style of drag?

No, and I think that’s one of the things that makes it so amazing is that everyone has their own unique style, and it’s all pretty much accepted. I started as a performer and a drag creature and there was space that was afforded to me and I transitioned to more glamor and pageantry and that’s afforded to me as well. I’ve been a bearded entertainer for a year now. The cool thing about Ohio is that there is literally a place for everyone.

I think I have everything I need. Is there anything else I didn’t ask you about that you want to bring up, or‚Ķ

I don’t think so. Are there any generic questions you haven’t asked?

Generic questions‚ĶI think I asked all of them already [laughs]. I like to ask what you’d be doing if you weren’t doing drag?

It’s a great question. I have a day job that is very demanding so I need drag to get away. I’m also very creative and artistic. I used to do web design and all these other things to pull into my creativity. Drag is the longest thing I’ve stuck with in all parts of my life, so I don’t think it’s going anywhere anytime soon.

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John deBary¬†is a drinks expert and writer. His first cocktail book,¬†Drink What You Want, is available now, and his next book,¬†Saved by the Bellini, is expected in early 2023. He is also the co-founder and president of the¬†Restaurant Workers’ Community Foundation, which is dedicated to improving the lives of hospitality industry professionals through advocacy, grant making, and impact investing.

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