Chicago’s Creepy Costume Contests for Halloween

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Navy Pier Cosplay Contest

Written by Dustin Ford

One of the most fun parts about Halloween is making your costume, but what’s the point of putting all that work in if no one sees it? You could show it off at a party or you could try to get something more out of it. If you are confident in your costume creation, then put your money where your mouth is and join one of these spooky costume contests!

Pinstripes Halloween Costume Contest

Much like Pinstripes, this contest is just as much for kids as it is for adults. Each will have their own contest on November 1st at 7 PM and 9 PM, respectively. There are special prizes for winners, but all participants receive complimentary gaming time and gift certificates. The worst-case scenario is that you get to bowl for free dressed up as Mario.

Spooky Euchre and Costume Contest at the Empty Bottle

This event is not for kids; it is for those 21 years of age and older. As the name implies, there will be a lot of people playing the card game Euchre and showing off their spooky duds. There are two separate contests: one for solo costumes and one for team costumes. The best solo costume wins a $40 bar tab, and that is double for the first-place team.

Cosplay at the Pier

There are costume contests for the kids and for amateur cosplayers, but the real show is for Professional Cosplayers! Chicago’s best crafters and sculptors come together to show off the spooky fruit of their horrific labor. This might be the highest production costume contest in Chicago. The first-place winner gets a grand prize and a $300 visa gift card.

Howl-O-Ween Pawty with Side by Side Pets

Yes, this costume contest is for your pets. All proceeds for this event will go to the Rescue ME Clifford organization. Bring your pooch and their best witch hat to this event and support a good cause. This is the most adorable costume contest around.