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Vintage Chicago T-Shirts

Our vintage Chicago t-shirts are made of a super-soft cotton/poly blend that feels like you’ve owned it for years.

All of our Chicago t-shirts are custom designed and screen printed using soft-hand vintage inks for a light worn feel. No thick heavy tees or gloppy inks here.

Shop Chicago T-Shirts

Chicago Posters and Vintage Chicago T-shirts

Windy City Prints is the premier collection of vintage Chicago posters and vintage Chicago t-shirts. All of our products are made of the highest quality materials and are designed by some of the top artists and illustrators in the country. We also feature a variety of vintage travel posters and vintage t shirts of other popular American cities like Boston, Nashville, New York and San Francisco. Check out some of our best selling featured products below.

Chicago Skyline Poster
This vintage Chicago skyline poster is the best selling print on our website. It is available in 2 easy-to-frame sizes. Check out this design along with all of the other vintage Chicago posters in our store.

Chicago Lakefront Poster
The Chicago Lakefront Poster by Anderson Design Group is our next best selling product at the Windy City Prints store. This Chicago poster features a gorgeous view of Lake Michigan at sunset with the iconic Chicago skyline and Hancock Tower in the background.

Free Chicago Stuff
Check out the Free Chicago Stuff section of our store to view all of our free Chicago stickers and free Chicago posters. Simply add any paid product from our store to your shopping cart and you can add one of our free Chicago items to your cart at no additional cost and no additional shipping and handling. Limit one free item per order.