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Popular Vintage Chicago T-Shirts & Shirts

389 results
Sunny Loganberry Fruit T-Shirt
Sunny Loganberry Fruit T-Shirt
Price$43.00
106 Miles To Chicago Baby T-Shirt
106 Miles To Chicago Baby T-Shirt
Price$28.45
The Lakefront Chicago, Illinois Baby T-Shirt
The Lakefront Chicago, Illinois Baby T-Shirt
Price$25.65
Dibs. Respect. T-Shirt
Dibs. Respect. T-Shirt
Price$43.00
RETRO TEE T-SHIRT GET YOUR KICKS ON ROUTE 66
RETRO TEE T-SHIRT GET YOUR KICKS ON ROUTE 66
Price$34.50
Womens Chicago Flag Southside Chicago City of Chic T-Shirt
Womens Chicago Flag Southside Chicago City of Chic T-Shirt
Price$47.80
CHI Chicago Flag T-Shirt
CHI Chicago Flag T-Shirt
Price$43.00
Chicago, IL - Enjoy the Lakefront T-Shirt
Chicago, IL - Enjoy the Lakefront T-Shirt
Price$34.50
Chicago Baby T-Shirt
Chicago Baby T-Shirt
Price$28.85
Lemon Henry Blind lemon jefferson 1926 T-Shirt
Lemon Henry Blind lemon jefferson 1926 T-Shirt
Price$43.00
Chicago Illinois Flag Tees Vintage Skyline Men W
Chicago Illinois Flag Tees Vintage Skyline Men W
Price$48.40
Chicago, IL - The Magnificent Mile T-Shirt
Chicago, IL - The Magnificent Mile T-Shirt
Price$34.50
Chicago Illinois Flag Tees Vintage Skyline Men Wo
Chicago Illinois Flag Tees Vintage Skyline Men Wo
Price$48.40
Chicago Illinois Flag Tees Vintage Skyline Shirt M
Chicago Illinois Flag Tees Vintage Skyline Shirt M
Price$48.40
Flag of Chicago T-Shirt
Flag of Chicago T-Shirt
Price$39.70
Vintage Distressed Chicago & Southern Airlines Tee
Vintage Distressed Chicago & Southern Airlines Tee
Price$44.80
Chicago ~ New York Central Lines T-Shirt
Chicago ~ New York Central Lines T-Shirt
Price$36.50
The Pioneer Zephyr 1934 T-Shirt
The Pioneer Zephyr 1934 T-Shirt
Price$53.80
RUN.HIDE CHICAGO SOUTHSIDE FUNNY T-Shirt
RUN.HIDE CHICAGO SOUTHSIDE FUNNY T-Shirt
Price$36.95
Visit Brookside Zoo Free T-Shirt
Visit Brookside Zoo Free T-Shirt
Price$36.55
Get Your Kicks Route 66 - Distressed Retro T-Shirt
Get Your Kicks Route 66 - Distressed Retro T-Shirt
Price$36.10
I heart Chicago Flag CHI T-Shirt
I heart Chicago Flag CHI T-Shirt
Price$43.00
Checkerboard Lounge Chicago Presents T-Shirt
Checkerboard Lounge Chicago Presents T-Shirt
Price$45.55
Chicago Illinois Flag Tees Vintage Skyline Men Wo
Chicago Illinois Flag Tees Vintage Skyline Men Wo
Price$49.60
Chicago Skyline Distressed American Flag T-Shirt
Chicago Skyline Distressed American Flag T-Shirt
Price$45.50
California Republic Chicago Transplant Flag Mashup T-Shirt
California Republic Chicago Transplant Flag Mashup T-Shirt
Price$60.70
Get Your Kicks - Route 66 - Vintage - Distressed T-Shirt
Get Your Kicks - Route 66 - Vintage - Distressed T-Shirt
Price$45.00
Al Capone T-shirt
Al Capone T-shirt
Price$43.00
Cute Chi-rish Chicago Irish T-Shirt
Cute Chi-rish Chicago Irish T-Shirt
Price$36.55
My Heart Belongs To Chicago Anniversary Quote 2022 T-Shirt
My Heart Belongs To Chicago Anniversary Quote 2022 T-Shirt
Price$48.40
Chicago Northwestern 1898 Chicago to California T-Shirt
Chicago Northwestern 1898 Chicago to California T-Shirt
Price$42.75
Chicago T-Shirt
Chicago T-Shirt
Price$36.50
1950 Chicago and North Western Railroad T-Shirt
1950 Chicago and North Western Railroad T-Shirt
Price$47.80
USS Chicago Coat of Arms t shirt
USS Chicago Coat of Arms t shirt
Price$32.70
Chicago, IL - 'L' Train T-Shirt
Chicago, IL - 'L' Train T-Shirt
Price$48.80
Chicago Flag Skyline T-Shirt
Chicago Flag Skyline T-Shirt
Price$36.50
Polish Eagle Vintage T-Shirt
Polish Eagle Vintage T-Shirt
Price$29.55
RETRO TEE T-SHIRT GET YOUR KICKS ON ROUTE 66
RETRO TEE T-SHIRT GET YOUR KICKS ON ROUTE 66
Price$35.90
Chicago Football T-Shirt
Chicago Football T-Shirt
Price$47.80
Lemon Henry Blind lemon jefferson 1926 T-Shirt
Lemon Henry Blind lemon jefferson 1926 T-Shirt
Price$34.50
Chicago World's Fair 1933 - Vintage Retro Art Deco T-Shirt
Chicago World's Fair 1933 - Vintage Retro Art Deco T-Shirt
Price$52.70
Abe Froman Sausage King of Chicago 1 T-Shirt
Abe Froman Sausage King of Chicago 1 T-Shirt
Price$47.80
Chicago - John Hancock Centre T-Shirt
Chicago - John Hancock Centre T-Shirt
Price$41.40
Chicago Style Capone t shirt
Chicago Style Capone t shirt
Price$45.55
The Ghoul Host of Creature Feature WGN Chicago T-Shirt
The Ghoul Host of Creature Feature WGN Chicago T-Shirt
Price$47.80
On a Scale of One To Ten Im a 262 Marathon T-Shirt
On a Scale of One To Ten Im a 262 Marathon T-Shirt
Price$47.80
Pre Marathon Checklist Funny Running T-Shirt
Pre Marathon Checklist Funny Running T-Shirt
Price$47.80
Chicago Urban Shirt
Chicago Urban Shirt
Price$53.05
S.S. Eastland as photographed by Pesha Postcard Co T-Shirt
S.S. Eastland as photographed by Pesha Postcard Co T-Shirt
Price$38.80
Chicago Rodeo, 1929. T-Shirt
Chicago Rodeo, 1929. T-Shirt
Price$54.90
Vintage logo Thor motorcycles T-Shirt
Vintage logo Thor motorcycles T-Shirt
Price$38.80
Get Your Kicks - Route 66 - Distressed 60's T-Shirt
Get Your Kicks - Route 66 - Distressed 60's T-Shirt
Price$45.00
Harrison Hotel Chicago T-Shirt
Harrison Hotel Chicago T-Shirt
Price$38.65
Chicago Vintage Guitars Concert Festival Souvenir Hoodie
Chicago Vintage Guitars Concert Festival Souvenir Hoodie
Price$88.20
North Avenue Beach Chicago Illinois Summer Vacatio T-Shirt
North Avenue Beach Chicago Illinois Summer Vacatio T-Shirt
Price$47.80
Chicago - Iconic Skyscrapers T-Shirt
Chicago - Iconic Skyscrapers T-Shirt
Price$40.75
1920s style dancing couple, Chicago music dark T-Shirt
1920s style dancing couple, Chicago music dark T-Shirt
Price$51.60
Chicago Flag Long Sleeve T Shirt
Chicago Flag Long Sleeve T Shirt
Price$36.20
Al Capone Tshirt Mafia
Al Capone Tshirt Mafia
Price$38.15
Hall of Science, Chicago World's Fair Retro T-Shirt
Hall of Science, Chicago World's Fair Retro T-Shirt
Price$32.70

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