Chicago Inspired Halloween Costumes

With Halloween right around the corner it’s time to start putting the finishing touches on your costume. Whether you’re just not inspired or haven’t had time to pick something up yet, we think that looking to our city can provide a tremendous amount of inspiration. With that in mind, check out these Chicago-centric costume ideas and show your Chicago pride this Halloween.

1. Coach Ditka

This one is a classic, but it’s so easy to pull off and it’s quintessential Chicago. For the Coach Ditka look all you need is the classic Bears sweater vest, some aviators, a mustache, and a shirt and tie. Luckily, Amazon has you covered on a Bears sweater or sweater vest if you don’t have one in the back of your closet.

2. Retro Bulls Super Fan

Pretty similar to the Ditka costume, you could also use the mustache and aviators to go with your retro Bulls gear. We’d definitely understand if you chose to rep the Bulls instead of the Bears with the season the Bears are having right now. Just make sure that your Chicago accent is on point!

3. Risky Business

This one is pretty simple to pull off. All you need is a white button down shirt and some very short shorts that are hidden by the length of the shirt. For the full look pair with some white socks and black sunglasses.

4. Mean Girls

Another classic option, you cannot go wrong with getting your Regina George look on this Halloween. You have a ton of routes here with all the amazing characters and the different outfits they wear throughout the movie, but we’re feeling classic Regina. You’ll need her go-to “A Little Bit Dramatic” tank which you can get here. To complete the look wear a pink cardigan over the tank and either a pleather black mini skirt or a pleated pink mini skirt, she is seen wearing both.

5. The Blues Brothers

Another classic Chicago getup, this look is extremely simple to pull off. All you need is a black suit, black tie, black hat, and black sunglasses. Represent Chicago in style this Halloween.

6. President Obama

Without a doubt one of Chicago’s favorite sons, you can’t go wrong with dressing up as our president this Halloween. All you need is your freshest suit and of course an Obama mask which you can find at just about any costume shop. If for some reason you can’t find one, we’ve got you covered here.

7. Flapper Girl

If you’re looking to throw it back even further than the Coach Ditka getup, the vintage 1920’s Chicago flapper girl is the perfect costume for you. Represent Chicago and the roaring twenties in style. Party City has a large selection of flapper girl costumes so you could surely find something you like.

8. Chance The Rapper

Another one of Chicago’s favorite sons here, rep Chance this Halloween to make sure you get on that ultra light beam. Chance has a number of looks, but you can pull off a great Chance costume by picking up some overalls and a classic White Sox cap.

9. Any Chicago Sports Player

Some may call it a cop out, but to us it’s just a really simple costume. Pull any of your Chicago sports jerseys and be your favorite Chicago athlete. Maybe you’re Patrick Kane or maybe you’re Kris Bryant, the choices are endless. Just please leave the old Derrick Rose jersey at home.

10. Ferris Bueller

An absolutely classic Chicago film, who doesn’t love Ferris Bueller? Channel your inner Ferris this Halloween with his full getup from the movie. Check out the costume here.

Couples Costume Idea: Ferris wouldn’t have nearly as much fun if it weren’t for his girl Sloane Peterson. Don’t spend Halloween without your girl; thankfully a full Sloane costume exists too. Check that out here.

11. CTA Track Worker

Ah, the wonderful CTA. Nothing in Chicago has a more love/hate relationship with its people than the CTA. This Halloween, dress up in blue and rock a one of those amazing neon construction vests and you just might end up getting to conduct a train car yourself! The CTA is probably cool with it, they even have a track worker kid’s costume.

12. Harry Caray

A Chicago icon, you can’t go wrong with the Harry Caray look this Halloween. All you need are some black, thick-framed glasses, white hair, suspenders, and a passion for Cubs baseball.

Written by @properties
At @properties, our goal is to provide you with expert, caring, and candid advice throughout one of the most important transactions you will ever make.