10 Halloween costumes that scream Chicago

From the Blues Brothers suit-and-sunglasses look to Blago’s infamous hair, Chicago history and pop culture are a wealth of Halloween costume ideas.

Risky Business

This 1983 flick set on the North Shore launched Tom Cruise’s movie career, made the El look like the least romantic place on earth … and provided a Halloween costume that’s still chuckle-worthy today. The lack of pants is problematic, especially on a chilly Chicago Halloween evening, so we recommend a good pair of tights to go with a sunglasses from the dollar store and an oversized button-down.

Willis Tower

Back in 1969, two Chicago architects were having lunch when one pulled out a pack of cigarettes. He put five in his fist in varying heights above his thumb and that was the design for the Sears, now Willis Tower. You can get the same effect with empty wrapping paper rolls. Attach a few gray pipe cleaners to a headband for the antennas and it’s a hometown hit.

Al Capone

Chicago’s most infamous gangster is a perfect way to bring a Halloween classic home. One of Grandpa’s old hats (or $10 at a costume store) tops off a simple costume of dress shirt, tie and suspenders.

Chicago Officials 

With the race wide open, the possibilities are endless. Cook County Sheriff Tom Dart? A standard’s sheriff’s star from a Western costume will do the trick. Rahm Emmanuel? Ballet tights and Touch-of-Gray hair dye should cover it.

Wayne’s World

Party on! Schwing! Wayne and Garth were the Blues Brothers of the ’90s. Ripped jeans, a tight black T-shirt and a black baseball hat for Wayne. Flannel shirt, a crazy blonde wig and a pair of drumsticks for Grath. Another great costume for two. Make sure to brush them up on their rendition of Queen’s Bohemian Rhapsody. Party on Wayne! Party on Garth!

Blues Brothers

Boots, black. Belt, black. One black suit jacket. One pair black suit pants. One hat. One pair black sunglasses, and your child is released (from your front door) and on a mission from God (for candy). Jake and Elwood make a great pairing for siblings or best friends. Polish up those Chicago accents and you’ll be sure they’ll be recognized by everyone they see. Save the suit and hat, lose the sunglasses, and you’ve got a great gangster costume for next year (see No. 5 above)

CTA Card

Only true Chicagoans will appreciate these retro CTA cards. A big piece of cardboard, some creative coloring and an angled cut in one corner your child will be unmistakable for that item we’ve all depended on to get us around each day.


Why just dress up as any old dinosaur when your child could be Sue, the world’s most beloved T-Rex? (You have to wonder how steep the competition is when it comes to flesh-eating reptiles). Add a name tag or if you’re feeling creative, a birthday hat (Sue turns 10 years old this year).

Crosstown classic

Think of it as a baseball-inspired version of Jekyll-and-Hyde costumes (we’ll let you decide which side is the genteel doctor and which is the murderous madman). Cut and restitch caps from each team and decorate a T-shirt and white sweatpants to match. (Adult-only version: Spend half the night talking about next year and the other half peppering your speech with expletives).

Red Eye Hawker/Box

You shouldn’t have any trouble tracking down a bundle or two of the Tribune’s Red Eye. Teach your child the patented pitch technique of those lovely men and women who greet us every morning on our way to work, and you’ve got a Chicago classic.

Variation: Paint a cardboard box red, get a Styrofoam sphere from an arts &crafts store, paint it red and attach it to a headband and go as an actual Red Eye box.

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