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Chicago-Centric Halloween Costumes for Kids

What do you get when you mix city pride with cute kids’ costumes? Some of the most memorable Halloween garb around! We asked trick-or-treaters to spill their best ideas for showing Chicago some love while stuffing their buckets full of treats.

Chicago-style hot dog

When Cait Sobotka asked her 2-year-old son, Theo, what he wanted to be for Halloween, his one-word answer was “bun.”

“The first thing that came to mind was a Chicago-style hot dog,” she says, complete with poppyseed bun, yellow mustard, chopped onions, sweet pickle relish and dill pickle spear. (Any Chicagoan can vouch: no ketchup!) After a trip to the craft store for pipe cleaners, felt and stuffing, Cait was able to make the costume in a couple of hours. “It wasn’t hard to make at all!”

And she says trick-or-treating around Chicago’s Logan Square neighborhood afterward brought plenty of smiles–and extra candy.

Local firestarters

A cow costume is cute anywhere, but when it’s paired with Mrs. O’Leary? Local genius. Last year, Angie Robertson saw siblings in this get-up and dubbed them the best costume of the night.

“It wasn’t even a cow costume specifically: They’d taken a Dalmatian dog costume and added a pink surgical glove at the waist for utters and a cow bell at the neck,” she says. “And the toddler had on a bonnet and lantern, for the perfect Mrs. O’Leary.”

Family affair

When Emily Boylan’s architecture-loving daughter asked to be the Sears Tower this year, Emily found a way to get the whole family involved: dress up as the Chicago skyline.

“Her brother will be the Hancock building, dad is going to be the Water Tower Place, and I’ll be the diamond building—also known as Crain Communications Building, one of the few downtown skyscrapers to be designed by a woman. Perfect fit!”

Vroom, vroom!

Tiana Kubik found the perfect way to pair her son’s love of all things racecar with her family’s love of Chicago.

“We put Griff in a NASCAR racing suit, but instead of generic sponsors, we picked some of our favorite local businesses,” she says. So with “sponsorship” patches and pins from faves like Bucktown Music, Purple Monkey Playroom and Building Blocks Toys, the 2-year-old was ready to hit the streets–with speed.

Bloody good architecture

Sometimes, a mash-up costume is short on sense but long on sweetness. So when Mycroft Tapey mentioned that the ideal costume would be Willis Tower ºand a vampire, the parents just rolled with it. Mom Nico fashioned the tower out of a giant swath of black felt and white piping, and the vampire piece was as easy as face paint and fake teeth.

Why the two ideas together?

“Because if I was a vampire and I went to Willis Tower, I’d never go hungry!” the 4-year-old says. It’s true!

Cubs love

Extend the baseball season well into fall with a Cubs baseball costume. Last year, Anna Pieta’s 6-year-old son, Luka, dressed up as Kris Bryant. “He’s a proud Cubbie, and he loved every moment of trick-or-treating when people were calling him Bryant,” she says. “He really took it to heart.”

And a costume doesn’t get much easier than a player’s jersey and a baseball cap!


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