Best Chicago Themed Halloween Costumes

If you find yourself coming to Chicago Halloween weekend, why not take some time and get into the Halloween spirit?  Let’s take it a step further and get into the Chicago spirit. Mix these spirits together and you’ve got a fantastic Halloween weekend cocktail. We encourage all of our guests at the hostel to wear their costumes. Casually at breakfast, cruising the halls, sleeping in your bunk, all of the above are perfectly acceptable times to rock your costume at Holiday Jones. It’s always fun to spook the international travelers with this weird, but awesome tradition that is really meant for children. Check out the best Chicago themed Halloween costumes below for inspiration.


The Billy Goat

billy goat costume

Too soon? Yes way too soon for our beloved cub fans, but it’s just so relevant right now. For those of you that have no idea what a billy goat has to do with Chicago, here is a quick cliff notes version. A long time ago some guy tried to bring his billy goat into Wrigley Field where Major League Baseball’s Chicago Cubs play. Management told the man he couldn’t bring his billy goat into the stadium so the man cursed the Chicago Cubs, saying they will never win a World Series again… and they haven’t since. They almost made it this year though. To add insult to injury you could always do a mix of a billy goat and a back to the future themed costume.


Stanley Cup

stanley cup costume

The Chicago Blackhawks (hockey team for all you non Canadians out there reading this) won the Stanley Cup this past year, last year and in 2010. They are now considered a dynasty. They are the only ray of sports sunshine in Chicago since the Bulls dynasty in the mid 90’s. All you really need is some tin foil, duck tape and some cardboard.

President Obama

obama mask

It’s the President’s last lap this year. Despite what you might think about him, it’s a really easy costume. You just need a suit and a mask. The masks are sold at every Halloween shop and online. In case you don’t get what this has to do with Chicago, it’s because he was a senator in Illinois and spent a lot of his time in Chicago. It’s considered his hometown.

Flapper Girl

Flapper girl costume

A fairly easy costume you just need a short skirt or dress with fruffy things hanging from it (full disclosure a man is writing this post), bob your hair, wear a funny hat and carry around a cigarette holder. It was the birth of the woman hipster. What does a flapper have to do with Chicago? They have that play called Chicago, which takes place in 1920’s Chicago and has a lot of flappers in it and as we stated at the beginning it’s called “Chicago”.

The Blues Brothers

blues brothers costume

Another easy costume of characters that are ingrained in Chicago culture. The Blue Brothers requires black suits, black ties, sunglasses, black fedora hat, and a mission from God.

SNL Chicago Bears Super Fans

snl chicago bears costume

Chris Farley (RIP), perfectly encompassed the Chicago bears fan stereo type. Actually just the Chicago stereotype in general. The heavy thick accent, bears sweater, Ditka obsession, and heart disease really brought it all to life. This one requires you to buy a bears jacket, but you can always use a good jacket. Don’t forget the aviators sunglasses and fake mustache.

Any Chicago Sports Player

Derrick Rose

This one should be easy enough. Although jerseys can be a bit expensive. We recommend going as Derrick rose of the Chicago Bulls and carry around a pair of crutches. That should go over well with most Bulls Fans.
The best part about these costume ideas is they can be used for other costumes with a minor switch. For the Blues Brothers, just add a cigar and fake tommy gun and you’re a old school gangster (still relevant to Chicago!). If you go as the SNL Bears Super fan, you can always just say you’re Mike Ditka next time around. If you choose the billy goat, just loose the Cubs paraphernalia and well… you’re a goat.

Happy Halloween!