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Shop Vintage Chicago T-Shirts

Discover Classic Designs Celebrating the Windy City

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Vintage Chicago

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Chicago Flag T-Shirt

T-Shirt

$19.99

Chicago City Skyline Flag Vintage Chicago City T-Shirt

T-Shirt

$19.99

Vintage Chicago Flag T-Shirt

T-Shirt

$19.99

Vintage Chicago Distressed T-Shirt

T-Shirt

$19.99

Chicago House Music Vintage Chicago Flag T-Shirt

T-Shirt

$19.99

Vintage Chicago Illinois Skyline Apparel T-Shirt

T-Shirt

$19.99

70s 80s USA City Vintage Chicago T-Shirt

T-Shirt

$19.99

Chicago Illinois Vintage Flag T-Shirt

T-Shirt

$19.99

Vintage Chicago Illinois Skyline Bears Football T-Shirt

T-Shirt

$19.99

Vintage Chicago Flag T-Shirt

T-Shirt

$19.99

Vintage Chicago Illinois Est. 1833 Gift T-Shirt

T-Shirt

$19.99

Vintage Chicago The Windy City Illinois EST 1848 T-Shirt

T-Shirt

$19.99

Vintage Chicago Illinois Est. 1833 Souvenir T-Shirt

T-Shirt

$19.99

Vintage Chicago Illinois Flag Tees Skyline T-Shirt

T-Shirt

$19.99

Chicago City Flag Distressed Bear Gift T-Shirt

T-Shirt

$19.99

Chicago City Flag Vintage T-Shirt

T-Shirt

$19.99

Chicago Flag 312 T-Shirt

T-Shirt

$19.99

Vintage Chicago Flag T-Shirt

T-Shirt

$19.99

Vintage Chicago Baseball Emblem T-Shirt

T-Shirt

$19.99

Chicago Flag Vintage T-Shirt

T-Shirt

$19.99

Chicago Vintage Skyline Retro Illinois Pride Gift T-Shirt

T-Shirt

$19.99

Chicago Illinois Stamp Logo T-Shirt

T-Shirt

$19.99

Cahokia Illinois Vintage Logo T-Shirt

T-Shirt

$19.99

Football Mack Attack 52 T-Shirt

T-Shirt

$19.99

Classic Vintage Retro Chicago Illinois Windy City Souvenir Great Gift T-Shirt

T-Shirt

$19.99

Wrigleyville Illinois Chicago Il Vintage T-Shirt

T-Shirt

$19.99

The Original Berf Of Chicagoland T-Shirt

T-Shirt

$19.99

All That Jazz T-Shirt

T-Shirt

$19.99

Chicago Vintage 80s Retro Style Funny Gift T-Shirt

T-Shirt

$19.99

Nope Not Again Funny Trump T-Shirt

T-Shirt

$19.99

Showing 1-30 of 92 designs

Dive into our collection of vintage Chicago t-shirts that feature iconic designs inspired by the city's rich culture and history. Shop unique styles and celebrate your love for the Windy City with our timeless tees today!

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