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10 Chicago-Inspired Halloween Costumes That Prove We Can Laugh At Ourselves

By Linze Rice | October 7, 2016 8:22am | Updated on October 14, 2016 11:16am
 Halloween is right around the corner, what could be scarier than taking a look at ourselves?
Halloween is right around the corner, what could be scarier than taking a look at ourselves?
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CHICAGO — Halloween is nearly upon us, and sometimes there's nothing scarier than taking a long, hard look in the mirror. 

Costumes inspired by Chicago life have always been a holiday mainstay: Can you remember the last party you went to that didn't have Blues Brothers or a Ditka?

But this year has been a special kind of roller coaster. We gained a pizza squirrellost a blob and gained — then lost — an enterprising duo from Arizona.

Make this Halloween a time of reflection and consider these costumes inspired by the last year in Chicago. 

But please: no clowns

• Brianna and Jaelin White: Chicago may remember the Whites from their brief visit to the city, which ultimately ended in a scuffle outside a Subway restaurant, move back to their home state and subsequent YouTube video explaining it all. Brianna and Jaelin took the city by storm, and while describing their experience in Chicago the couple took the time to put the situation into context by describing the outfits they were wearing. Recreating the look comes in two steps, the Brianna and the Jaelin. In their own words:


Lovvvvaaaaaa boooyy 😝

A photo posted by Brianna Joy White (@briannawhite) on

Jaelin: "I had a white polo on ... and short, like, shorts and stuff like that, kind of preppy," Jaelin said.

Pro tip — no need to buy an actual Ralph Lauren polo shirt, as Brianna noted, Jaelin's was "fake."

Brianna: "I was wearing high-waisted shorts, a crop top and a denim jacket without the sleeves," Brianna said.

To be clear, that is not a jean vest she is referring to, it's a denim jacket draped over the shoulders. Easy-peasy!

[Facebook/Don Miller]

• Cubs Half-Beard Man: Don Miller of Lincoln Square wants the Cubs to win the World Series so bad he shaved off half of his growing beard and has vowed to shave the other half when they do. To match Miller, do exactly as he did: Put on your best Cubs gear, take a deep breath and shave half your beard off right down the middle. (Or buy a fake one, cut it in half, and voilà).

• Montrose Avenue Blob: Chicago had developed an unusual affinity for a blob of fungal matter that spilled from a yard and onto the sidewalk before it vanished last month. For Linda and Larry Bartoli, "The Blob" that oozed from their Montrose Avenue yard has been a fixture and curious oddity in their North Center neighborhood. Linda has suggested it may be the ghost of a tree, but either way, its spirit can live on through you.

[DNAinfo/Patty Wetli]

The only requirement for this look is that your costume take on a blobby shape in shades of green and black — so pile on sweaters or blankets and perch on a curb. Bonus partner look: "the blob thief."

 Lost Bob Newhart: For years Bob Newhart played a Chicago psychologist in "The Bob Newhart Show." For someone as learned and detail-oriented as a psychologist must be, Newhart had an awful hard time commuting from River North to Edgewater. So much so in fact his flip-flopping route home must have taken hours.

[Screenshot; DNAinfo/Linze Rice]

His look is easy: grab a tan or brown trench coat, black hat and gloves, briefcase and wear some sort of suit and tie underneath. Accessories can, and probably should, include a map of Chicago and your Ventra card.

• Chance The (W)Rapper: One of Chicago's favorite sons, Chance the Rapper, is living his best Halloween life starring alongside his son in a Kit Kat commercial. To be Halloween Chance, snag a lion costume, throw on a red baseball cap and line your pockets with the classic candy bar.

If available, tote around your mini-me, younger sibling or patient dog and dress them as an adorable lion as well. Want classic Chicago Chance? Throw on a T-shirt, a pair of overalls and crown yourself with a Sox hat. 

• Urban Hermit: A new study revealed Chicago as the No. 1 spot for "urban hermits," meaning people who just want to be left alone with their snacks and internet thrive here. Can you blame them? We can't, and it makes for a super simple costume that starts Halloween morning by not brushing your hair or changing out of pajamas.


Bring along whatever accessories best describe you: a bucket of chicken, a pair of headphones, the box set of "The Wire," a small sack of Donettes — whatever feels right. Don't engage with anyone unless you want to. Sneak upstairs during a party at someone else's house and kick back with some Netflix. 

• Lincoln Towing Pirate: Arrrgh! This city surely does not like the shenanigans linked to Lincoln Towing, but there's no denying its reputation for illegal towing lends itself to a pretty great costume. Wear a mechanic's jumpsuit, pirate hat and eye patch, grab a hook and dangle a Hot Wheels car from it. 

• Lester Holt's Mustache: Noticeably absent for city dwellers who watched the first presidential debate was moderator and journalist Lester Holt's bold, bushy mustache. Holt sported his once-famous mustache as a reporter for CBS2 Chicago, and video from that time, mustache and all, continues to play at the Cook County Criminal Courthouse.

[Cook County]

Those days are long over but could be resurrected Halloween night by putting on your best suit, grabbing a cordless microphone and slapping on (or growing your own) newsman mustache. For the truly skillful, get some cardboard and paint and become the mustache itself. 

• Pizza Squirrel: Every city needs a hero, and Chicago has found one in Pizza Squirrel. Buy or make a matching set of fuzzy ears and a tall tail, don a brown sweatshirt and sweatpants and swing by Bacci's on your way out for an appropriately sized slice. If you have good upper body strength, climb a tree and eat your pizza there, in peace.

• Dibs-er: Halloween is the perfect time to be "that guy." You know what we're talking about — the controversial Chicago winter code known as "dibs."

To be the dibs-er, simply wear your Chiberia winter garb, clutch a folding chair or cone and look suspiciously at everyone. Bring a notebook and pen to leave passive-aggressive notes everywhere you go telling the person how you spent two hours cleaning up after Mother Nature and therefore you are entitled to that spot forever. Optional partner costume: an anti-dibser to follow you around removing all your notes.

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