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Chicago T-Shirts From the Hometown of Threadless

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Threadless started as a t-shirt company in Chicago in 2000, so we take Chicago t-shirts personally. Deep dish, Italian beef, hot dogs and river bridges, all drawn by independent artists and printed on demand. The artist earns on every sale. Curious how it began? Read the Threadless story.

  1. CHICAGO BARS
    CHICAGO BARS by bossdog
  2. Vintage Chicago Bears Mascot
    Vintage Chicago Bears Mascot by Harebrained
  3. Chicago Style Pizza Box
    Chicago Style Pizza Box by Harebrained
  4. Don't Be A Monster, Take The Train
    Don't Be A Monster, Take The Train by Harebrained
  5. Tear It Up In Chicago
    Tear It Up In Chicago by Harebrained
  6. Da Pope
    Da Pope by Phineas X. Jones
  7. The Wetter The Better
    The Wetter The Better by Harebrained
  8. Retro Chicago Hot Dog
    Retro Chicago Hot Dog by 5EyeStudio
  9. State Street Bridge
    State Street Bridge by ScienceMarchChi
  10. Chicago Pride
    Chicago Pride by k_lukes
  11. Chicago Dog with Everything
    Chicago Dog with Everything by Phineas X. Jones
  12. Chicago Lit since 1871
    Chicago Lit since 1871 by Harebrained
  13. Chicago Tsunami Flag
    Chicago Tsunami Flag by transittees
  14. Chicago Dive Bars
    Chicago Dive Bars by Harebrained
  15. Pope Chicago
    Pope Chicago by Harebrained
  16. Malörtov Cocktail
    Malörtov Cocktail by Phineas X. Jones
  17. Chicago Italian Beefs
    Chicago Italian Beefs by Harebrained
  18. Wrigley Field Chicago Cubs Artwork by Marian Nixon Paintings
    Wrigley Field Chicago Cubs Artwork by Marian Nixon Paintings by Marian1
  19. Chicago Glizzies
    Chicago Glizzies by Harebrained
  20. Sürly Türt (on dark colors)
    Sürly Türt (on dark colors) by Phineas X. Jones
  21. Chicago
    Chicago by chidm
  22. Oh Hey Chicago!
    Oh Hey Chicago! by campkatie
  23. Gone Feral In Chicago
    Gone Feral In Chicago by kilkennycat
  24. Chicago Hot Dog (Pink)
    Chicago Hot Dog (Pink) by 5EyeStudio
  25. Chicago Cubs Champions
    Chicago Cubs Champions by 5EyeStudio
  26. CHICAGO MAP
    CHICAGO MAP by JazzberryBlue
  27. Bulls (Red)
    Bulls (Red) by 5eth
  28. DA BEARS
    DA BEARS by bossdog
  29. Threadless Hot Dog
    Threadless Hot Dog by Steger
  30. C.O.W.L.
    C.O.W.L. by radiantblack
  31. Bulls (Grey)
    Bulls (Grey) by 5eth
  32. Bulls (Black)
    Bulls (Black) by 5eth
  33. Bulls (White)
    Bulls (White) by 5eth
  34. Blue Tiger
    Blue Tiger by ppmid
  35. "Chicago Knows How to Handle ICE"
    "Chicago Knows How to Handle ICE" by craightonberman
  36. Chicago Cicada Mascot
    Chicago Cicada Mascot by Harebrained
  37. Abolish Ice
    Abolish Ice by Harebrained
  38. Cheers, Chicago
    Cheers, Chicago by Harebrained
  39. Chicago House Music Rocks
    Chicago House Music Rocks by Harebrained
  40. Chicago Wet Beefs
    Chicago Wet Beefs by Harebrained
  41. Hey Chicago
    Hey Chicago by losereputation
  42. Chicago Rat with Chicago Dog
    Chicago Rat with Chicago Dog by annalisaillo
  43. The Chicago Grid System
    The Chicago Grid System by Harebrained
  44. Chicago Style Scorpion
    Chicago Style Scorpion by Phineas X. Jones
  45. Vintage Chicago Bulls Mascot
    Vintage Chicago Bulls Mascot by Harebrained
  46. Vintage Chicago Baseball Northside Team
    Vintage Chicago Baseball Northside Team by Harebrained
  47. CTA: One El Of A Ride
    CTA: One El Of A Ride by Harebrained
  48. Chicago Mothman Mascot
    Chicago Mothman Mascot by Harebrained
* Comparison prices are references to regular retail prices of the same or similar items in Artist Shops or at third party retail locations. Savings may vary over time.