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6 Halloween costumes that will show off your Chicago pride

Zach Long
Written by
Zach Long

Halloween is almost here and your busy schedule may not have allowed you the time to brainstorm a getup to wear to seasonal parties and concerts. Not to fear: We came up with six costumes that will showcase your Chicago pride (and a bit of creativity). You still have enough time to craft or cobble together these outfits—just stop by one of our favorite Halloween costume stores if you need some help.

RECOMMENDED: Our complete guide to Halloween in Chicago

Illustrations by Andrew Rae

Fly Boy

If Chance the Rapper can dress like Hebru Brantley’s iconic street art creation (as he did in his “Angels” music video), so can you. Pretend to take flight while wearing yellow goggles, a green cap and a red bandana.

Old Style sign

Turn yourself into a glowing signifier of a decent dive bar by donning a sandwich board depicting the regional beer logo and “hanging out” in front of your favorite corner tavern. Don’t be surprised if everyone asks you for a Chicago Handshake.


Celebrate the city’s most loved slash loathed winter tradition by dressing in a white sheet (get a little muddy if you’re striving for authenticity) and draping yourself in lawn chairs, old tires and any other junk that might occupy a freshly shoveled parking spot.

Marina City towers

Finally, a costume for the couple that goes on architecture tours together. You and your significant other should sport matching duds (or cardboard box creations) displaying the towers’ signature “corn cob” pattern. Be warned: Wilco fans will mistake you for Yankee Hotel Foxtrot.

Paul McGee

Whipping up a tribute to Chicago’s foremost tiki purveyor is easier than mixing a Tic-Tac-Taxi cocktail. Just throw on a fake beard, some hip glasses (clear frames are in) and a tasteful Hawaiian shirt.

Commissioner’s Trophy

Yes, we’re going to keep gloating about the Cubs’ 2016 World Series win while we hope for a repeat. Mimic the championship hardware by wearing a Cubs uniform and a crown of 30 tiny flags. For the full effect, have a friend hoist you up in Grant Park.

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