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1000+ items
Hats
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1000+ items
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Vintage Chicago Optical Illusion Steampunk Skyline Dad Hat
Robert Lucio
$25.19
Illinois Retro Cassette Tape Dad Hat
Whimspired By Paxx
$25.19
Chicago Black Hawk Dad Hat
ZamboniZingers
$25.19
Chicago Retro Script Typography Dad Hat
Drizzlers
$41.98
Chicago City windy City Sticker Baseball Cap
mnkyride
$23.09
More for the City Collection... Baseball Cap
Harold122Jade
$28.34
Illinois Central Vintage Logo Dad Hat
Trains-and-Rail
$23.09
Lake Erie and Western Railroad Dad Hat
Trains-and-Rail
$23.09
Chicago Skyline Minimalist Line Art Dad Hat
MinimalLine
$25.19
Chicago Sunday Morning Breakfast Club Est 1920 Retro Tailgate Baseball Cap
PunPals-Art
$24.98
Cool Chicago Bear Sunglasses Striped Hat Vintage Graphic Baseball Cap
PunPals-Art
$24.98
Chicago Bear Wearing Santa Hat And Sunglasses Christmas Vintage Dad Hat
dartoffofo⭐⭐⭐⭐⭐
$24.98
California Zephyr Neon Drumhead Dad Hat
Trains-and-Rail
$23.09
Chicago Dad Hat
Cole Design Works
$25.19
Chicago Night 4 October 13 Music Tour Fan Design Baseball Cap
LouisaOReilly
$29.39
Illinois Gen X Skateboard Dad Hat
Whimspired By Paxx
$25.19
Champaign Minimalistic Map Art Baseball Cap
MapsNerd
$24.56
Chicago Dad Hat
OlympicsMerch
$25.19
City Life — Chicago Dad Hat
New-Blood
$23.09
chicago bears Baseball Cap
theandroidvivz
$25.19
chicago bears Dad Hat
theandroidvivz
$25.19
chicago bears Baseball Cap
theandroidvivz
$25.19
Chicago Bears Dad Hat
theandroidvivz
$25.19
chicago bears Dad Hat
theandroidvivz
$25.19
chicago bears Dad Hat
theandroidvivz
$25.19
chicago bears Baseball Cap
theandroidvivz
$25.19
chicago bears Baseball Cap
theandroidvivz
$25.19
Chicago Bears Dad Hat
onlytiggokk
$25.19
Chicago Bears Dad Hat
onlytiggokk
$25.19
Chicago Bears Baseball Cap
onlytiggokk
$25.19
Chicago Bears Dad Hat
onlytiggokk
$25.19
Chicago Bears Baseball Cap
onlytiggokk
$25.19
Chicago Bears Dad Hat
onlytiggokk
$25.19
Chicago Bears Baseball Cap
onlytiggokk
$25.19
Local Chicagoan's Know This One Dad Hat
Brett Rosenberg
$26.24
Sweet Vintage Retro Chicago City Flag Bear Printa Baseball Cap
DuneHaicna
$26.24
The Chicago Bean Art Dad Hat
BlueBerry45
$23.09
Chicago Bears 59 Point Explosion Windy City Football Week 1 2026 Dad Hat
yuckticke
$25.19
Chicago And Styx The Windy Cities Tour Baseball Cap
guiceltsaxe3
$25.19
CHICAGO Baseball 18 94 Vintage Retro Illinois USA Baseball Cap
AliciaGu867850
$27.58
Naperville Minimalistic Map Art Dad Hat
MapsNerd
$24.56
Chicago Flag Grunge Vintage Distressed Graphic | Windy City Pride Retro Design Dad Hat
GarnerSupplyCo
$25.19
The Windy City Chicago Dad Hat
midsco
$25.19
Chicago Dad Hat
spicecarnerl
$25.19
Illinois City Watercolor – Chicago, Pizza & Route 66 Baseball Cap
Marie Gems
$25.19
Southside Religious Baseball Fan Art Baseball Cap
KACIIBARN
$25.19
Chicago Illinois USA Line Art Skyline Poster Dad Hat
CMYKStudio
$25.19
Chicago Illinois Bubble Letter Personalized City Collage Baseball Cap
joshuarose9
$23.09
Chicago Skyline City Pride Basketball Dad Hat
eManiar94
$33.69
Chicago Skyline - Aerial View Baseball Cap
DGMaxShop
$25.19
TBT: Chicago - The Bean - Vintage Polaroid Pop Art Baseball Cap
ByJeffro
$23.09
Illinois Prairie and Skyline Guitar Baseball Cap
Whimspired By Paxx
$25.19
Lou Mitchell's Chicago Streetscape with Willis Tower and Neon Sign Baseball Cap
Aryabek
$27.92
Lou Mitchell's Chicago Diner with Willis Tower City Landmark Baseball Cap
Aryabek
$27.92
Illinois Dog Dad Hat
Whimspired By Paxx
$25.19
City Life — Chicago Baseball Cap
New-Blood
$23.09
Funny Chicago Football Bear Graphic | Windy City Sports Fan Humor | Best Gift Dad Hat
FisnikR
$34.84
Windy City Football Vintage Retro Distressed Graphic Design For Chicago Sports Fans And Gridiron Enthusiasts | Limited Edition Baseball Cap
FisnikR
$34.84
Awesome Chicago Baseball Fan Design - South Side Windy City Sports Graphic | ⭐⭐⭐⭐⭐ Dad Hat
FisnikR
$34.84
Chicago Bear Cool Sunglasses City Pride Sketch Dad Hat
Snyder93
$25.19
Chicago Baseball Cap
happymoon03
$24.98
Chicago Baseball Cap
jadynbennionv
$25.19
Illinois Chicago Blues Dog Dad Hat
Whimspired By Paxx
$25.19
Chicago Football Vintage Retro Helmet Dad Hat
BobbyTate64654
$31.59
Vintage Chicago Skyline Illinois Adventure Dad Hat
T-Motive
$23.09
Wrigleyville Chicago Baseball Dad Hat
cuvavirtuex
$25.19
Chicago Bears Illinois Nfl State Outline Baseball Cap
markeytaggw
$25.19
Cubs Baseball Cap
markeytaggw
$25.19
Chicago Music Blues Great Lakes City Skyline Badge Baseball Cap
RDproject
$25.19
Chicago Deep Dish Pizza Skyline Foodie Souvenir Badge Dad Hat
RDproject
$25.19
The Windy City NFL Football Chicago Illinois Bears Caleb Williams, Obama, Mike Ditka Baseball Cap
Space Ghettos
$23.09
NFL Football Player QB Chicago Bears Star Caleb Williams NCAA Oklahoma USC Baseball Cap
Space Ghettos
$23.09
Windy City Football Fan Vintage Retro Distressed Graphic Design For Chicago Sports Enthusiasts | Best Gift Baseball Cap
FisnikR
$34.84
Chicago Illinois Urban Population Map Retro Aesthetic Graphic Design | Limited Edition Baseball Cap
TzmMedia
$34.84
Oak City Dad Hat
adhamisouhis
$25.19
Chicago Theatre Baseball Cap
adinecalli
$23.09
Chicago Football Fan Navy Orange City Pride | Windy City Game Day Sports Aesthetic | ⭐⭐⭐⭐⭐ Dad Hat
FisnikR
$34.84
Windy City Football Pride Retro Vintage Style Graphic Design For Chicago Sports Fans And Gridiron Enthusiasts | Limited Edition Baseball Cap
Junkers
$34.84
Chicago Vintage Retro USA Travel Dad Hat
RareDeerArt
$25.19
Chicago Windy City Pattern Dad Hat
TinyWeird
$25.19
Chicago Dreams – The Windy City Baseball Cap
RockitBaby
$25.19
Chicago Inspired Cute Chicago Bean with Chicago flag components Baseball Cap
aligchi
$25.40
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