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  1. Impressive: He's even got a white dot for every El stop. Who needs a map when you've got your entire left side?

  2. Deeply regrettable: Folks, feast your eyes upon this Mike Ditka minion tattoo. Yes, it happened. 

  3. Truly regrettable: Contrary to popular belief, it's not cool to have a convicted felon on your arm.

  4. Impressive: The best love letter to a city can fit on a postcard.

  5. 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.

  6. Impressive: Wait, how long did that take to make!? The details on each iconic Chicago skyscraper are beautiful. 

  7. Truly regrettable: That font is "Chi-Shitty."

  8. 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? 

  9. Truly regrettable: We love the Chicago flag/pizza combo, but...A little effort here, folks!

  10. Truly regrettable: Did you have to put it on your head?

  11. Impressive: Not taking yourself too seriously seems to be the way to go with Chicago tattoos. This Mike Ditka bear certainly accomplishes that goal.

  12. Truly regrettable: How long do you have to wait before removing a tattoo?

  13. Of dubious taste: Is there anything less appetizing than a hot dog emblazoned on someone's shoulder?

  14. Impressive: Bartenders always know what kind of shots this guy is going to order.

  15. Of dubious taste: Tired of the same old Chicago flag tattoos? Give yours a power-up.

  16. Truly regrettable: How did a Space Jam logo not make the cut?

  17. Impressive: Clean and simple lines make this tat as distinctive as the Willis Tower's antennas.

  18. Of dubious taste: When it comes to Blackhawks tattoos, this is as tasteful as it gets.

  19. Impressive: Is it possible to get tiny, blinking lights embedded in your skin?

  20. Truly regrettable: You won't find this obscure Van Gogh piece at the Art Institute.

  21. Truly regrettable: If you're going to use cliché nicknames for the city, you should use them correctly.

  22. 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. 

  23. 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

Written 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

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