Worldwide icon-chevron-right North America icon-chevron-right United States icon-chevron-right Illinois icon-chevron-right Chicago icon-chevron-right The most impressive and regrettable Chicago tattoos

Heads up! We’re working hard to be accurate – but these are unusual times, so please always check before heading out.

Impressive: He's even got a white dot for every El stop. Who needs a map when you've got your entire left side?
Deeply regrettable: Folks, feast your eyes upon this Mike Ditka minion tattoo. Yes, it happened. 
Truly regrettable: Contrary to popular belief, it's not cool to have a convicted felon on your arm.
Impressive: The best love letter to a city can fit on a postcard.
Of dubious taste: We admire the dedication, but this collection of signatures from the entire 1985 Bears team looks like a prank gone horribly wrong.
Impressive: Wait, how long did that take to make!? The details on each iconic Chicago skyscraper are beautiful. 
Truly regrettable: That font is "Chi-Shitty."
Impressive, yet regrettable: Not quite sure where this one falls. On the one hand, the colors, details and scope of this full leg tattoo are incredible. On the other hand...Why? 
Truly regrettable: We love the Chicago flag/pizza combo, but...A little effort here, folks!
Truly regrettable: Did you have to put it on your head?
Impressive: Not taking yourself too seriously seems to be the way to go with Chicago tattoos. This Mike Ditka bear certainly accomplishes that goal.
Truly regrettable: How long do you have to wait before removing a tattoo?
Of dubious taste: Is there anything less appetizing than a hot dog emblazoned on someone's shoulder?
Impressive: Bartenders always know what kind of shots this guy is going to order.
Of dubious taste: Tired of the same old Chicago flag tattoos? Give yours a power-up.
Truly regrettable: How did a Space Jam logo not make the cut?
Impressive: Clean and simple lines make this tat as distinctive as the Willis Tower's antennas.
Of dubious taste: When it comes to Blackhawks tattoos, this is as tasteful as it gets.
Impressive: Is it possible to get tiny, blinking lights embedded in your skin?
Truly regrettable: You won't find this obscure Van Gogh piece at the Art Institute.
Truly regrettable: If you're going to use cliché nicknames for the city, you should use them correctly.
Deeply regrettable: There are many cool ways to do a Chicago flag tattoo. A nipple-grazing square with birds poking at not one of them. 
Regrettable: Didn't know it was possible to make the Chicago flag look gross. 

The most impressive and regrettable Chicago tattoos

Before you go under the gun, take a look at some inked-up tributes to Chicago

By Grace Perry

Walk through the crowd at a music festival like Riot Fest, and you'll see plenty of people sporting tattoo tributes to the city of Chicago and its various cultural institutions, including a lot of hot dogs and Bears logos. We realize that it can be hard to encapsulate everything that you love about a place in a single image, so we found examples of Chicago-inspired ink, ranging from impressive to truly regrettable. Whether you’re looking for inspiration or dissuasion, we’ve got you covered.

RECOMMENDED: Our guide to living in Chicago


    You may also like