Set your cookie preferences

We use cookies, please see our Cookie Notice for more information. By clicking "Accept Cookies" you consent to our use of cookies.

Search for products or designs

Sell on Zazzle쑢Shopping Cart

WeddingsOpens a menu with links to top wedding-related pages.

Wedding Invitations ➞
Wedding Stationery ➞
Be My Bridesmaid Cards
Bridal Shower Invites
Enclosure Cards
Engagement Party Invites
Bachelorette Party Invitations
Reception Invites
RSVP Cards
Save the Dates
Thank You Cards
Wedding Décor ➞
Guest Books
Menus
Napkins
Place Cards
Plates
Programs
Seating Charts
Wedding Signs
Table Numbers
Favour Packaging ➞
Beer Labels
Can Coolers
Favour Bags
Favour Tags
Magnets
Stickers & Labels
Water Labels
Wine Bottle Labels
Showers & Parties ➞
Bridal Shower Supplies
Bachelorette Party Supplies
Wedding Gifts ➞
Bridesmaid Gifts
Groomsmen Gifts

All Weddings ➞

Wedding Stationery & Décor
From save the dates to signage, design every detail of your day.

Invitations & StationeryOpens a menu with links to top invitations & stationery-related pages.

Birthday Invitations ➞
Kids' Birthday Invitations
Adult Birthday Invitations
Joint Birthday Invitations
1st Birthday Invitations

Baby Invitations ➞
Baby Shower Invitations
Birth Announcements
More Invitations ➞
Christening Invitations
Christmas Invitations
Communion Invitations
Graduation Invitations
Halloween Invitations
Moving Announcements
Party Invitations
Greeting Cards ➞
Anniversary Cards
Birthday Cards
Christmas Cards
Father's Day Cards
Graduation Cards
Mother's Day Cards
New Baby Cards
Thank You Cards
Valentine's Cards
Personal Stationery ➞
Note Cards
Postcards
Post-it® Notes

Mailing Accessories ➞
Envelopes
Envelope Seals
Return Address Labels
Rubber Stamps & Ink

All Invitations & Stationery ➞

Cards & Invitations 
Personalise premium stationery for any event or milestone.

Gift Wrap & Party SuppliesOpens a menu with links to top crafts & party supplies-related pages.

Gift Wrapping ➞
Gift Bags
Gift Tags
Ribbon
Stickers & Labels
Tissue Paper
Wrapping Paper
Party Signs ➞
Backdrops
Banners
Posters & Prints
Party Stationery ➞
Guest Books
Menus
Place Cards
Programs
Table Numbers
Party Tableware ➞
Paper Cups
Paper Bowls
Paper Napkins
Paper Plates
Favours & Packaging ➞
Can Coolers
Favour Bags
Favour Boxes
Favour Tags
Food & Drink Labels

All Gift Wrap & Party ➞

Gift Wrap & Party Supplies
Make their day with personalised wrapping & party decorations.

Business EssentialsOpens a menu with links to top office & school-related pages.

Business Cards ➞
Bakery Business Cards
Beauty Business Cards
Construction Business Cards
DJ Business Cards
Hair Stylist Business Cards
QR Code Business Cards
Name Tags & Badges ➞
Marketing Materials ➞
Appointment Cards
Brochures
Flyers
Gift Certificates
Loyalty Cards
Menus & Price Lists
Referral Cards
Displays & Packaging ➞
Display Cards
Hang Tags & Inserts
Product Labels

Business Stationery ➞
Notebooks
Post-it® Notes
Rubber Stamps & Ink
Business Signs ➞
Banners
Posters & Prints
Window Decals

Calendars ➞

All Business ➞

Business Essentials
Boost your brand with quality business cards & marketing materials.

Art & HomeOpens a menu with links to more categories of top pages.

Mugs ➞
Funny Mugs
Photo Mugs

Barware ➞
Beer Glasses
Can Coolers
Shot Glasses
Whiskey Glasses
Wine Glasses
More Homeware ➞
Aprons
Blankets
Ornaments
Pillows
Posters & Prints ➞
Abstract Posters
Botanical Posters
Fine Art Posters
Nursery Posters
Travel Posters
Vintage Posters

Art & Home 
Style your space with personalised posters, cushions, mugs & more.

T-Shirts & Accessories

T-Shirts ➞
Men's T-Shirts
Women's T-Shirts

Birthday T-Shirts
Funny T-Shirts
Photo T-Shirts
Vintage T-Shirts
Wedding T-Shirts
Accessories ➞
Buttons
Beach Towels
Hats
Luggage Tags
Socks
Ties
Tote Bags
Sports & Games ➞
Golf Balls
Playing Cards
Puzzles

T-Shirts, Tote Bags & More
From business to birthdays to bridal showers, customise items for any occasion.

Create Your OwnOpens a menu with links to top Create-Your-Own products.

T-Shirts & Accessories
Badges
Hats
Socks
Ties
Tote Bags
T-Shirts

Sports & Games
Golf Balls
Playing Cards
Puzzles
Art & Home
Aprons
Blankets
Ornaments
Pillows
Mugs
Posters
Gift Wrap & Party
Paper Napkins
Party Signs
Stickers
Wrapping Paper
Business
Business Cards
Flyers
Badges
Post-it® Notes
Invitations & Stationery
Greeting Cards
Guest Books
Invitations
Menus
Programs
Return Address Labels
Rubber Stamps
Save the Dates

All Create Your Own ➞

Create Your Own
Make your own mugs, t-shirts & more with our easy design tool.

Popular Vintage Chicago T-Shirts & Shirts

Popular Vintage Chicago T-Shirts & Shirts

448 results

Cotton

Blends

Premium Tri-Blends

Short Sleeve...

Hoodie...

Pocket...

Standard

Extended Sizing

Unisex

Fitted

Short Sleeve...

Long Sleeve...

$25 to $50

$50 to $75

$75 to $100

Anderson Design Group...

Saturday Evening Post Sports Collection...

StockTrek Images...

Lantern Press Store...

University of Wyoming Information...

Fabric

Style

Colour

Size & fit

Sleeve length

Price

Design Style

Officially Licensed

Special Picks

Events & Occasions

Recipients

Brand

Creator Store

Makers

Design Options

Number of Photos

Design Colour

f_zevt

Sort by:

Save 15%

Retro Chicago Vintage Script T-Shirt

Sale Price CA$48.28.CA$48.28 Original Price CA$56.80.CA$56.80

Save 15%

Vintage Chicago German Flag Eagle T-Shirt

Sale Price CA$42.59.CA$42.59 Original Price CA$50.10.CA$50.10

Save 15%

Chicago Flag Plaid Vintage t shirt

Sale Price CA$34.17.CA$34.17 Original Price CA$40.20.CA$40.20

Save 15%

Chicago House Music - Vintage DJ Old School EDM T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Chicago House Music Disco EDM DJ Vintage T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Vintage Chicago house est 1984 House party DJ T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Chicago House Music Vintage Vinyl Dj Raver Flag Sk T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Vintage Foot Paw Bear Orange Chicago T-Shirt

Sale Price CA$45.27.CA$45.27 Original Price CA$53.25.CA$53.25

Save 15%

Chicago House Music - Vintage Stylish EDM Rave T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Chicago Police (VINTAGE) T-Shirt

Sale Price CA$42.59.CA$42.59 Original Price CA$50.10.CA$50.10

Save 15%

CHICAGO IL ILLINOIS Vintage Retro Style Men Women T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Chicago Police VINTAGE STAR T-Shirt

Sale Price CA$29.29.CA$29.29 Original Price CA$34.45.CA$34.45

Save 15%

Chicago Police VINTAGE STAR T-Shirt

Sale Price CA$34.17.CA$34.17 Original Price CA$40.20.CA$40.20

Save 15%

Retro Vintage Chicago Skyline City 70s 80s Souveni T-Shirt

Sale Price CA$45.27.CA$45.27 Original Price CA$53.25.CA$53.25

Save 15%

Wrigleyville Chicago Vintage T-Shirt

Sale Price CA$45.27.CA$45.27 Original Price CA$53.25.CA$53.25

Save 15%

Chicago Police VINTAGE STAR T-Shirt

Sale Price CA$42.59.CA$42.59 Original Price CA$50.10.CA$50.10

Save 15%

Chicago Skylines Retro Vintage Style For Chicagoan T-Shirt

Sale Price CA$45.27.CA$45.27 Original Price CA$53.25.CA$53.25

Save 15%

Lincoln Park, Chicago 1915 Vintage T-Shirt

Sale Price CA$38.72.CA$38.72 Original Price CA$45.55.CA$45.55

Save 15%

Chicago Teachers Union Red For Ed Vintage Apple Sh T-Shirt

Sale Price CA$45.27.CA$45.27 Original Price CA$53.25.CA$53.25

Save 15%

Chicago Flag T-shirt

Sale Price CA$32.30.CA$32.30 Original Price CA$38.00.CA$38.00

Save 15%

Chicago Police (VINTAGE) T-Shirt

Sale Price CA$34.17.CA$34.17 Original Price CA$40.20.CA$40.20

Save 15%

Chicago House Music - Dj Turntable Vintage Edm T-Shirt

Sale Price CA$45.82.CA$45.82 Original Price CA$53.90.CA$53.90

Save 15%

Chicago Style Hot Dog Lover Summer Vintage T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Chicago Style Hot Dog Lover Summer Vintage T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Chicago House Music - Vinyl DJ Vintage T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Chicago Bullsss Vintage T-Shirt

Sale Price CA$36.30.CA$36.30 Original Price CA$42.70.CA$42.70

Save 15%

Chicago Skyline Retro Vintage Vaporwave Cyberpunk T-Shirt

Sale Price CA$45.27.CA$45.27 Original Price CA$53.25.CA$53.25

Save 15%

Vintage Chicago Ferris Wheel T-Shirt

Sale Price CA$37.15.CA$37.15 Original Price CA$43.70.CA$43.70

Save 15%

Vintage Chicago Skyline City Baseball T-Shirt

Sale Price CA$45.27.CA$45.27 Original Price CA$53.25.CA$53.25

Save 15%

Chicago House Music - Stylish Flag Vintage Dance T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Chicago Retro Vintage Souvenir 60s 70s Distressed T-Shirt

Sale Price CA$46.41.CA$46.41 Original Price CA$54.60.CA$54.60

Save 15%

Vintage Chicago Police Operation Crime Stop T-Shirt

Sale Price CA$40.80.CA$40.80 Original Price CA$48.00.CA$48.00

Save 15%

Chicago Vintage Baseball for Men and Women T-Shirt

Sale Price CA$45.27.CA$45.27 Original Price CA$53.25.CA$53.25

Save 15%

Chicago Teachers Union Red For Ed Vintage Apple Sh T-Shirt

Sale Price CA$45.27.CA$45.27 Original Price CA$53.25.CA$53.25

Save 15%

Chicago Teachers Union Red For Ed Vintage Apple Sh T-Shirt

Sale Price CA$45.27.CA$45.27 Original Price CA$53.25.CA$53.25

Save 15%

Vintage chicago T-Shirt

Sale Price CA$37.23.CA$37.23 Original Price CA$43.80.CA$43.80

Save 15%

Chicago World's Fair 1933 - Vintage Retro Art Deco T-Shirt

Sale Price CA$42.76.CA$42.76 Original Price CA$50.30.CA$50.30

Save 15%

Chicago World's Fair 1933 - Vintage Retro Art Deco T-Shirt

Sale Price CA$48.28.CA$48.28 Original Price CA$56.80.CA$56.80

Save 15%

Chicago World's Fair 1933 - Vintage Retro Art Deco T-Shirt

Sale Price CA$54.79.CA$54.79 Original Price CA$64.45.CA$64.45

Save 15%

Chicago House Music Disco EDM DJ Vintage Rave T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Vintage Chicago Flag Polish Eagle Heritage T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Vintage Chicago Flag Essential T-Shirt

Sale Price CA$51.73.CA$51.73 Original Price CA$60.85.CA$60.85

Save 15%

Chicago House Music - Skyline EDM Vintage T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Retro Chicago City Stripes Illinois Vintage T-Shirt

Sale Price CA$31.11.CA$31.11 Original Price CA$36.60.CA$36.60

Save 15%

Vintage Worlds Fair Chicago 1934 T Shirt

Sale Price CA$35.45.CA$35.45 Original Price CA$41.70.CA$41.70

Save 15%

Chicago Blues Music Vintage T-shirt Mens Womens Un

Sale Price CA$60.27.CA$60.27 Original Price CA$70.90.CA$70.90

Save 15%

Chicago House Music - Vintage EDM DJ Retro Disco T-Shirt

Sale Price CA$44.71.CA$44.71 Original Price CA$52.60.CA$52.60

Save 15%

Chicago Subway Map w/ Train stops vintage T-Shirt

Sale Price CA$47.18.CA$47.18 Original Price CA$55.50.CA$55.50

Save 15%

Vintage CHICAGO Flag T-Shirt

Sale Price CA$73.10.CA$73.10 Original Price CA$86.00.CA$86.00

Save 15%

Chicago Skyline Vintage Travel T-Shirt

Sale Price CA$41.10.CA$41.10 Original Price CA$48.35.CA$48.35

Save 15%

Chicago Skyline Vintage Chicago Illinois T-Shirt

Sale Price CA$56.87.CA$56.87 Original Price CA$66.90.CA$66.90

Save 15%

Illinois State Pride Chicago Skyline Illustration T-Shirt

Sale Price CA$41.48.CA$41.48 Original Price CA$48.80.CA$48.80

Save 15%

Chicago House Music Vintage Illinois Dj Raver Chic T-Shirt

Sale Price CA$56.87.CA$56.87 Original Price CA$66.90.CA$66.90

Save 15%

Chicago House Music Vintage Vinyl Dj Raver Flag Sk T-Shirt

Sale Price CA$56.87.CA$56.87 Original Price CA$66.90.CA$66.90

Save 15%

Chicago L 1950 Watercolor Sepia Photograph Subway T-Shirt

Sale Price CA$50.79.CA$50.79 Original Price CA$59.75.CA$59.75

Save 15%

Chicago L 1950 Watercolor Sepia Photograph Subway T-Shirt

Sale Price CA$50.79.CA$50.79 Original Price CA$59.75.CA$59.75

Save 15%

Chicago T Shirt - Vintage Chicago Flag Theme Skyli

Sale Price CA$44.20.CA$44.20 Original Price CA$52.00.CA$52.00

Save 15%

Vintage Downtown Chicago City Skyline Walking-Bear T-Shirt

Sale Price CA$56.87.CA$56.87 Original Price CA$66.90.CA$66.90

Save 15%

Chicago Blackhawk restaurant 1960's Photo Original T-Shirt

Sale Price CA$48.16.CA$48.16 Original Price CA$56.65.CA$56.65

Save 15%

The El Dorados "At My Front Door" T-Shirt – 1950s

Sale Price CA$40.25.CA$40.25 Original Price CA$47.35.CA$47.35

쎂Previous 1 2 3 4 5 Next쎃

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?

YesNo

If you need help or have a question for Customer Service, please visit our Help Centre