Threadless
Sell
Your Art

Chicago T-Shirts From the Hometown of Threadless

Show: Products/Designs
Sort by: Relevance/Trending/Popular/New

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. Abolish Ice
    Abolish Ice by Harebrained
  2. Chicago
    Chicago by chidm
  3. Chicago Dive Bars
    Chicago Dive Bars by Harebrained
  4. Oh Hey Chicago!
    Oh Hey Chicago! by campkatie
  5. Chicago Fan Bear
    Chicago Fan Bear by coyote_alert
  6. Wrigley Field Chicago Cubs Artwork by Marian Nixon Paintings
    Wrigley Field Chicago Cubs Artwork by Marian Nixon Paintings by Marian1
  7. Retro Chicago Hot Dog
    Retro Chicago Hot Dog by 5EyeStudio
  8. Malörtov Cocktail
    Malörtov Cocktail by Phineas X. Jones
  9. DA BEARS
    DA BEARS by bossdog
  10. "Chicago Knows How to Handle ICE"
    "Chicago Knows How to Handle ICE" by craightonberman
  11. Chicago Italian Beefs
    Chicago Italian Beefs by Harebrained
  12. Chicago Pride
    Chicago Pride by k_lukes
  13. Chicago Style Pizza Box
    Chicago Style Pizza Box by Harebrained
  14. Bulls (Black)
    Bulls (Black) by 5eth
  15. Chicago House Music Rocks
    Chicago House Music Rocks by Harebrained
  16. Chicago Dog with Everything
    Chicago Dog with Everything by Phineas X. Jones
  17. Chicago Two Flat
    Chicago Two Flat by joemills
  18. Bulls (Red)
    Bulls (Red) by 5eth
  19. Chicago Picasso
    Chicago Picasso by joemills
  20. CHICAGO MAP
    CHICAGO MAP by JazzberryBlue
  21. State Street Bridge
    State Street Bridge by ScienceMarchChi
  22. Gone Feral In Chicago
    Gone Feral In Chicago by kilkennycat
  23. Chicago Hot Dog (Pink)
    Chicago Hot Dog (Pink) by 5EyeStudio
  24. Chicago Cubs Champions
    Chicago Cubs Champions by 5EyeStudio
  25. Threadless Hot Dog
    Threadless Hot Dog by Steger
  26. C.O.W.L.
    C.O.W.L. by radiantblack
  27. CHICAGO BARS
    CHICAGO BARS by bossdog
  28. Bulls (Grey)
    Bulls (Grey) by 5eth
  29. Bulls (White)
    Bulls (White) by 5eth
  30. Chicago Tsunami Flag
    Chicago Tsunami Flag by transittees
  31. Pope Chicago
    Pope Chicago by Harebrained
  32. Chicago Cicada Mascot
    Chicago Cicada Mascot by Harebrained
  33. Cheers, Chicago
    Cheers, Chicago by Harebrained
  34. Vintage Chicago Bears Mascot
    Vintage Chicago Bears Mascot by Harebrained
  35. Chicago Wet Beefs
    Chicago Wet Beefs by Harebrained
  36. Chicago Glizzies
    Chicago Glizzies by Harebrained
  37. Hey Chicago
    Hey Chicago by losereputation
  38. Chicago Lit since 1871
    Chicago Lit since 1871 by Harebrained
  39. Chicago Rat with Chicago Dog
    Chicago Rat with Chicago Dog by annalisaillo
  40. The Chicago Grid System
    The Chicago Grid System by Harebrained
  41. Chicago Style Scorpion
    Chicago Style Scorpion by Phineas X. Jones
  42. Vintage Chicago Bulls Mascot
    Vintage Chicago Bulls Mascot by Harebrained
  43. Vintage Chicago Baseball Northside Team
    Vintage Chicago Baseball Northside Team by Harebrained
  44. CTA: One El Of A Ride
    CTA: One El Of A Ride by Harebrained
  45. The Wetter The Better
    The Wetter The Better by Harebrained
  46. Chicago Mothman Mascot
    Chicago Mothman Mascot by Harebrained
  47. Vintage Southside Chicago Baseball Mascot
    Vintage Southside Chicago Baseball Mascot by Harebrained
  48. Chicago
    Chicago by coyote_alert
* 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.