Popular Vintage Chicago T-Shirts & Shirts
Chicago Skyline Retro Sunset: Vintage Willis Tower
Men's T-Shirts
Chicago Vintage
Women's T-Shirts
Chicago Police VINTAGE STAR
Boys' T-Shirts

Popular Vintage Chicago T-Shirts & Shirts

655 results
Abe Froman Sausage King of Chicago 1 T-Shirt
Abe Froman Sausage King of Chicago 1 T-Shirt
PriceCA$52.60
Alco C-628 aka Alco Century 628 Diesel Locomotive T-Shirt
Alco C-628 aka Alco Century 628 Diesel Locomotive T-Shirt
PriceCA$41.80
Alco C-628 aka Alco Century 628 Diesel Locomotive T-Shirt
Alco C-628 aka Alco Century 628 Diesel Locomotive T-Shirt
PriceCA$53.85
Polish Eagle Chicago Flag T-Shirt
Polish Eagle Chicago Flag T-Shirt
PriceCA$52.60
Wings of a Century T-Shirt
Wings of a Century T-Shirt
PriceCA$56.80
Harrison Hotel Chicago T-Shirt
Harrison Hotel Chicago T-Shirt
PriceCA$42.55
S.S. Eastland as photographed by Pesha Postcard Co T-Shirt
S.S. Eastland as photographed by Pesha Postcard Co T-Shirt
PriceCA$42.70
Polish Eagle Vintage T-Shirt
Polish Eagle Vintage T-Shirt
PriceCA$32.55
Pope Leo Pope Bob First American Pope Vintage Papa T-Shirt
Pope Leo Pope Bob First American Pope Vintage Papa T-Shirt
PriceCA$47.15
Chicago Rodeo, 1929. T-Shirt
Chicago Rodeo, 1929. T-Shirt
PriceCA$60.45
Officially Licensed
I Got Rimmed At The Chicago Auto Show T-Shirt
I Got Rimmed At The Chicago Auto Show T-Shirt
PriceCA$52.60
Chicago Style Pizza Deep Dish Pizza Thick Crust Fo T-Shirt
Chicago Style Pizza Deep Dish Pizza Thick Crust Fo T-Shirt
PriceCA$52.60
312 Area Code Chicago City Sports T-Shirt
312 Area Code Chicago City Sports T-Shirt
PriceCA$52.60
Manson Bicyle T T-Shirt
Manson Bicyle T T-Shirt
PriceCA$44.80
Alco C-628 aka Alco Century 628 Diesel Locomotive T-Shirt
Alco C-628 aka Alco Century 628 Diesel Locomotive T-Shirt
PriceCA$45.95
North Avenue Beach Chicago Illinois Summer Vacatio T-Shirt
North Avenue Beach Chicago Illinois Summer Vacatio T-Shirt
PriceCA$52.60
World's Fair Chicago Souvenir Map, 1893 T-Shirt
World's Fair Chicago Souvenir Map, 1893 T-Shirt
PriceCA$54.60
Chicago House Music Vintage Vinyl Dj Raver Flag Sk T-Shirt
Chicago House Music Vintage Vinyl Dj Raver Flag Sk T-Shirt
PriceCA$66.90
Chicago, IL - 'L' Train T-Shirt
Chicago, IL - 'L' Train T-Shirt
PriceCA$38.00
Officially Licensed
Buckingham Fountain On Chicago's Lake Front T-Shirt
Buckingham Fountain On Chicago's Lake Front T-Shirt
PriceCA$53.20
Al Capone Tshirt Mafia
Al Capone Tshirt Mafia
PriceCA$42.00
Chicago - Iconic Skyscrapers T-Shirt
Chicago - Iconic Skyscrapers T-Shirt
PriceCA$44.80
Chicago 2021 Marathon 26 T-Shirt
Chicago 2021 Marathon 26 T-Shirt
PriceCA$52.60
Irish Italian Drinking Team T-Shirt
Irish Italian Drinking Team T-Shirt
PriceCA$71.00
SUPA COOL MAN - DON'T U REMEMBER ME? T-Shirt
SUPA COOL MAN - DON'T U REMEMBER ME? T-Shirt
PriceCA$65.90
Funny Bigfoot Rock And Roll For Sasquatch Believer T-Shirt
Funny Bigfoot Rock And Roll For Sasquatch Believer T-Shirt
PriceCA$60.80
1920s style dancing couple, Chicago music dark T-Shirt
1920s style dancing couple, Chicago music dark T-Shirt
PriceCA$56.80
Dibs. Respect. T-Shirt
Dibs. Respect. T-Shirt
PriceCA$47.35
I Love Illinois T-Shirt
I Love Illinois T-Shirt
PriceCA$45.55
Retro Brookfield Zoo panda T-Shirt
Retro Brookfield Zoo panda T-Shirt
PriceCA$56.80
Chicago Northwestern 1898 Chicago to California T-Shirt
Chicago Northwestern 1898 Chicago to California T-Shirt
PriceCA$47.05
70'S 80'S Usa City Chicago T-Shirt
70'S 80'S Usa City Chicago T-Shirt
PriceCA$66.90
Chicago Chi Arched Text Distressed Red Print T-Shirt
Chicago Chi Arched Text Distressed Red Print T-Shirt
PriceCA$66.90
70'S 80'S Usa City Chicago T-Shirt
70'S 80'S Usa City Chicago T-Shirt
PriceCA$66.90
Retro Chicago Pigeon T-Shirt
Retro Chicago Pigeon T-Shirt
PriceCA$56.40
Retro Chicago Pigeon T-Shirt
Retro Chicago Pigeon T-Shirt
PriceCA$45.25
Vintage Fire Extinguisher Advertising T-Shirt
Vintage Fire Extinguisher Advertising T-Shirt
PriceCA$60.85
1912 Chicago, The Summer Resort T-Shirt
1912 Chicago, The Summer Resort T-Shirt
PriceCA$48.80
Chicago Style Capone t shirt
Chicago Style Capone t shirt
PriceCA$47.35
Chicago City Flag Distressed Bear T-Shirt
Chicago City Flag Distressed Bear T-Shirt
PriceCA$60.85
Chicago - Hometown Pride - Throwback Design - Clas T-Shirt
Chicago - Hometown Pride - Throwback Design - Clas T-Shirt
PriceCA$66.90
Pink Chicago Illinois Il Varsity Style On Chicago T-Shirt
Pink Chicago Illinois Il Varsity Style On Chicago T-Shirt
PriceCA$66.90
Chicago Happy Halloween Vintage Style 1 T-Shirt
Chicago Happy Halloween Vintage Style 1 T-Shirt
PriceCA$52.60
Chicago Flag Distressed Vintage Style Pride Men Wo T-Shirt
Chicago Flag Distressed Vintage Style Pride Men Wo T-Shirt
PriceCA$66.90
Chicago, IL - The Magnificent Mile T-Shirt
Chicago, IL - The Magnificent Mile T-Shirt
PriceCA$38.00
Officially Licensed
USS Chicago Coat of Arms t shirt
USS Chicago Coat of Arms t shirt
PriceCA$36.00
Get Your Kicks - Route 66 - Distressed 60's T-Shirt
Get Your Kicks - Route 66 - Distressed 60's T-Shirt
PriceCA$49.55
Vintage OK Used Cars Sign - You Type a Dealership T-Shirt
Vintage OK Used Cars Sign - You Type a Dealership T-Shirt
PriceCA$48.00
Chicago Hockey Retro Vintage Blackhawks Inspired 9 T-Shirt
Chicago Hockey Retro Vintage Blackhawks Inspired 9 T-Shirt
PriceCA$52.60
Cub Style Vintage Chicago T-Shirt
Cub Style Vintage Chicago T-Shirt
PriceCA$52.60
Art Institute 44th Exhibition T-Shirt
Art Institute 44th Exhibition T-Shirt
PriceCA$54.60
1967 Chicago Spurs Vintage Soccer T-Shirt
1967 Chicago Spurs Vintage Soccer T-Shirt
PriceCA$52.60
My Tribute to Schwinn Vintage Bicycles of Chicago T-Shirt
My Tribute to Schwinn Vintage Bicycles of Chicago T-Shirt
PriceCA$52.60
Hall of Science, Chicago World's Fair Retro T-Shirt
Hall of Science, Chicago World's Fair Retro T-Shirt
PriceCA$36.00
Chicago Antique Map, LaSalle Street and River T-Shirt
Chicago Antique Map, LaSalle Street and River T-Shirt
PriceCA$48.85
Oktoberfest Chicago Flag German Eagle Vintage T-Shirt
Oktoberfest Chicago Flag German Eagle Vintage T-Shirt
PriceCA$49.00
Chicago and Southern Air Lines logo T-Shirt
Chicago and Southern Air Lines logo T-Shirt
PriceCA$47.35
Vintage Chirish Shamrock Chicago Flag T-Shirt
Vintage Chirish Shamrock Chicago Flag T-Shirt
PriceCA$50.10
chicago T-Shirt
chicago T-Shirt
PriceCA$41.80
Chicago Flag Distressed Vintage Style Pride Men Wo T-Shirt
Chicago Flag Distressed Vintage Style Pride Men Wo T-Shirt
PriceCA$47.35

The Zazzle Promise

  • Love It Guarantee

    Don't love it? We'll take it back! 30-day returns “100% Love It Guarantee.”

  • Easy International Delivery

    Hassle-free shipping with no surprise fees. We cover any customs & duties.

  • Secure Shopping Guaranteed

    100% Secure payment with SSL Encryption.

Search Feedback

Did you find what you were looking for?
If you need help or have a question for Customer Service, please visit our Help Centre