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Retro Chicago Posters
1000+ items
Posters
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1000+ items
Most Relevant
Ferris Bueller - Sears Tower Poster
twelfthman
$17.53
$21.91
(20% off)
1970 Old Town Art Fair Poster
Old Town Triangle Association
$15.72
$19.64
(20% off)
Chicago Retro Skyline Badge - Illinois City Travel Design Poster
Lyfeinsights
$14.51
$18.13
(20% off)
1971 Old Town Art Fair Poster
Old Town Triangle Association
$15.72
$19.64
(20% off)
1972 Old Town Art Fair Poster
Old Town Triangle Association
$15.72
$19.64
(20% off)
1977 Old Town Art Fair Poster
Old Town Triangle Association
$15.72
$19.64
(20% off)
David Hockney - Chicago Exhibition Poster
ChristopherBann
$16.32
$20.40
(20% off)
Bueller's Car Ferris Coll Poster
Andrea-Gardner
$18.13
$22.67
(20% off)
Ferris Bueller - Pom Bensin Krawang Poster
anissendong
$14.51
$18.13
(20% off)
Aretha Franklin Vintage Poster
janewatsones
$15.72
$19.64
(20% off)
Ferris Bueller Sears Tower Screenprint Poster Poster
SoulGlowDesigns
$15.11
$18.89
(20% off)
Chicago Vice Poster
warungetatee
$14.51
$18.13
(20% off)
Chicago Vintage Travel Poster Poster
vintagevivian
$20.55
$25.69
(20% off)
Chicago Poster Retro Movie Poster
Andreaede
$16.20
$20.25
(20% off)
Visit Chicago Poster
Mercury Club
$17.53
$21.91
(20% off)
Da Big Three Poster
HoopHeritage
$20.55
$25.69
(20% off)
Chicago sunset by Sasa Elebea Poster
Sabrina Brugmann
$18.86
$23.57
(20% off)
Chicago Illinois Skyline Travel Art Vintage Poster
KrisSidDesigns
$14.81
$18.51
(20% off)
Chicago Vintage Travel Poster Poster
TravelerRat
$14.51
$18.13
(20% off)
Take flight. Poster
HoopHeritage
$20.55
$25.69
(20% off)
Chicago Llama Poster
Yolande Sukal
$14.51
$18.13
(20% off)
MY OWN BEST FRIEND (vintage illustration) Poster
ART INSPIRED BY MUSIC
$18.13
$22.67
(20% off)
Copy of Vintage Chicago Band Poster
Terryhaynezza
$16.93
$21.15
(20% off)
Illinois Chicago Cloud Gate Retro Skyline Illustration Poster
PeerMstudio
$13.30
$16.62
(20% off)
Chicago of Today - The Metropolis of the West 1893 Poster
molamode
$14.99
$18.74
(20% off)
War Stare Jordan Poster
HoopHeritage
$15.72
$19.64
(20% off)
The composer Herbie Poster
longrafae
$13.66
$17.07
(20% off)
Steampunk Airship: Admiral Rosendahl Poster
forge22
$14.51
$18.13
(20% off)
Art institute Chicago retro Poster
aapshop
$15.11
$18.89
(20% off)
Chicago Vintage Travel Poster Poster
TravelerRat
$14.51
$18.13
(20% off)
CHICAGO THE WINDY CITY Poster
123ks
$17.53
$21.91
(20% off)
chicago illinois city poster Poster
Arctic frame studio
$15.11
$18.89
(20% off)
Chicago Vintage Travel Poster Poster
vintagevivian
$20.55
$25.69
(20% off)
Chicago USA City Poster
Alexandra Rty
$14.51
$18.13
(20% off)
Little Walter retro styled poster Poster
konstk
$14.51
$18.13
(20% off)
Walter Payton Sweetness Poster
PatsFanToro
$12.82
$16.02
(20% off)
Pre-Game Thoughts Poster
HoopHeritage
$15.72
$19.64
(20% off)
Chicago Skyline Vintage Retro City Illustration Poster
Andruzito
$14.51
$18.13
(20% off)
CHICAGO MAP Poster
JazzberryBlue
$17.53
$21.91
(20% off)
CHICAGO : Vintage 1893 Worlds Fair Advertising Print Poster
posterbobs
$14.51
$18.13
(20% off)
Vintage Chicago Illinois South Shore Line Vintage Ski Travel Poster
cutesy
$20.55
$25.69
(20% off)
Vienna Beef NK-17 Poster Poster
TheRDA
$14.51
$18.13
(20% off)
Chicagofest 1981 Poster
Retrorockit
$14.51
$18.13
(20% off)
Chicago American Airlines Poster
MarryHafford
$18.13
$22.67
(20% off)
Indiana Dunes National Park Poster
Stadify
$14.51
$18.13
(20% off)
Vintage Masterpiece: Nighthawks by Edward Hopper, c. 1942 - Classic Artwork with Rich History and Timeless Charm Poster
THASSON
$14.51
$18.13
(20% off)
Chicago Windy City Vintage Flag Shirt | Retro Chicago Skyline Travel Graphic Tee Poster
LoppiPrintShop
$13.90
$17.38
(20% off)
Derrick Rose MVP Chicago Basketball Signature Vintage Retro 80s 90s Bootleg Rap Style Poster
Isabella Heller ⭐⭐⭐⭐⭐(316)
$15.72
$19.64
(20% off)
Me and Bro Poster
HoopHeritage
$20.55
$25.69
(20% off)
1989 Old Town Art Fair Poster
Old Town Triangle Association
$15.72
$19.64
(20% off)
1978 Old Town Art Fair Poster
Old Town Triangle Association
$15.72
$19.64
(20% off)
Chicagofest 1979 Poster
Retrorockit
$14.51
$18.13
(20% off)
CHICAGO VINTAGE ART Poster
MarkedArtPrints
$15.72
$19.64
(20% off)
20th Century Limited, 1938. Vintage Poster Poster
historyphoto
$13.30
$16.62
(20% off)
retro classic Chicago poster Poster
CorasPosters
$14.51
$18.13
(20% off)
Visit Lake Michigan Poster
Mercury Club
$17.53
$21.91
(20% off)
1966 Old Town Art Fair Poster
Old Town Triangle Association
$15.72
$19.64
(20% off)
CHICAGO NAVY PIER VINTAGE ART Poster
MarkedArtPrints
$15.72
$19.64
(20% off)
Climax Blues Band Distressed Poster
Receivirarts
$18.13
$22.67
(20% off)
connor bedard retro design Poster
aksav
$14.51
$18.13
(20% off)
Visit Chicago Poster
Mercury Club
$17.53
$21.91
(20% off)
Buckingham Fountain Chicago Retro Poster - Vintage Chicago Tourism 1939 Poster
molamode
$14.99
$18.74
(20% off)
1980 Old Town Art Fair Poster
Old Town Triangle Association
$15.72
$19.64
(20% off)
WLS MusicRadio Chicago Poster
TeeArcade84
$15.11
$18.89
(20% off)
Derrick Rose MVP Chicago Basketball Signature Vintage Retro 80s 90s Bootleg Rap Style Poster
Isabella Heller ⭐⭐⭐⭐⭐(316)
$15.72
$19.64
(20% off)
1980's Chicago Door Poster
KWAPhoto
$14.51
$18.13
(20% off)
Tribune Sunday Chicago Vintage Poster Woman with Poppies Poster
LP
$22.97
$28.71
(20% off)
Giraffe in Town Poster
MsGonzalez
$19.95
$24.93
(20% off)
Chicago Football Retro Game Day Poster
toutwearapparel
$14.51
$18.13
(20% off)
Chicago Vintage Poster Poster
DimDom
$16.32
$20.40
(20% off)
Southside Boys, 1941. Vintage Photo Poster
historyphoto
$13.30
$16.62
(20% off)
1979 Old Town Art Fair Poster
Old Town Triangle Association
$15.72
$19.64
(20% off)
CHICAGO: Vintage 1893 Worlds Fair Advertising Print Poster
posterbobs
$14.51
$18.13
(20% off)
Chicago Blues Poster
samhi113
$14.66
$18.32
(20% off)
Hammond-Bears Retro Stripes Poster
VintageViolet79
$14.51
$18.13
(20% off)
Visit Chicago Poster
Mercury Club
$17.53
$21.91
(20% off)
Chicago Retro Vintage Travel Poster Poster
vintagevivian
$20.55
$25.69
(20% off)
Micheal Jordan Poster
DD Fish
$15.11
$18.89
(20% off)
Mr. Dennis Rodman Poster
tanbaobu
$16.93
$21.15
(20% off)
Chicago Windy City Retro Graphic Shirt | Vintage Chicago Flag Travel Design Poster
LoppiPrintShop
$13.90
$17.38
(20% off)
1987 Old Town Art Fair Poster
Old Town Triangle Association
$15.72
$19.64
(20% off)
Chicago Vintage Travel Poster
Vintage-Travel
$15.72
$19.64
(20% off)
Chicago Baseball Haven Poster
Bored Imagination
$14.51
$18.13
(20% off)
Chicago Art Deco Poster
ArtDecoGecko
$14.51
$18.13
(20% off)
Chicago Retro Skyline - Chicago Retro Sunset, Gift for Chicago Lover Poster
AITeeGenius
$13.30
$16.62
(20% off)
Chicago Retro Skyline - Chicago Retro Sunset, Retro Art Poster
AITeeGenius
$13.30
$16.62
(20% off)
Retro Wesley Willis Visual Tribute Poster
acquiesce13
$18.01
$22.51
(20% off)
St. Patrick's Day-Minimal Retro Vintage - Chicago Goes Green - St. Patrick's Day 2026 Design Poster
pod24
$16.93
$21.15
(20% off)
Chicago Cyberpunk Poster
FuturiTravel
$14.51
$18.13
(20% off)
Ron Hardy House Music Legend Poster
Tribal Uprising Inc
$13.30
$16.62
(20% off)
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Wall Art
Poster
Retro Chicago
Retro Chicago posters have a bright white base for sharp images and vibrant color reproduction. Sizes are custom cut based on the artist’s creation.
Chicago
Retro
Vintage
Illinois
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