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The most impressive and regrettable Chicago tattoos

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


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 it...is not one of them. 


Regrettable: Didn't know it was possible to make the Chicago flag look gross. 

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


Alyssa tastemaker

Aw, come on, what's dubious about the Hawks tattoo?

Cleighton D
Cleighton D

Bad news: some of these are really terrible tattoos. Good news: Sempurna Restoration Clinic can remove them. Come visit our River North loft.