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Windy City Caps
1000+ items
Hats
Filters (2)
1000+ items
Newest
THE FRIENDLY CONFINDS Dad Hat
thatDudeAZ89
$19.62
$23.09
(15% off)
Chicago Retro Skyline Badge - Illinois City Travel Design Dad Hat
Lyfeinsights
$21.41
$25.19
(15% off)
Chicago Town Baseball Cap
CristianoArt
$20.99
$26.24
(20% off)
Did You Just Look At My Wiener? Chicago Style Hot Dog Graphic Baseball Cap
ThreadRiotTees
$20.15
$25.19
(20% off)
Circular Emblem with Red Hot Dog and Four White Stars Dad Hat
AndrijaArt
$21.41
$25.19
(15% off)
Stevie Shay and Evan Zanders from mile high Baseball Cap
Artist Avenue
$23.17
$28.97
(20% off)
Chicago City Skyline Architecture Travel Resident Tourist Baseball Cap
Simsimah26Parks
$25.19
$31.49
(20% off)
Chicago Basketball Vintage Skyline Dad Hat
RonnyMilleo
$19.62
$23.09
(15% off)
Chicago Pride Illinois T-Shirt – Windy City Fan Tee | Uncle Jichuan Dad Hat
Uncle-Jichuan
$20.52
$24.14
(15% off)
City of Chicago Baseball Cap
arifeTshirt
$18.47
$23.09
(20% off)
Chicago, USA - Blue Abstract Art Baseball Cap
shadow-bloom
$20.15
$25.19
(20% off)
Nico 1988 Windy City Covert Agent Baseball Cap
ELFENNEC
$20.15
$25.19
(20% off)
Vintage Baseball Script Dad Hat
Snaztastic
$24.98
$29.39
(15% off)
Golden Chicago Rare Japanese Kanji Calligraphy Funny Windy City Gift Art Dad Hat
noworries-art
$19.62
$23.09
(15% off)
Bulls Red Chicago Japanese Kanji Calligraphy Funny Windy City Souvenir Art Dad Hat
noworries-art
$19.62
$23.09
(15% off)
THE WINDY CITY CHICAGO Baseball Cap
likbatonboot
$20.15
$25.19
(20% off)
THE WINDY CITY CHICAGO Baseball Cap
likbatonboot
$20.15
$25.19
(20% off)
THE WINDY CITY CHICAGO Baseball Cap
likbatonboot
$20.15
$25.19
(20% off)
THE WINDY CITY CHICAGO Dad Hat
likbatonboot
$21.41
$25.19
(15% off)
THE WINDY CITY CHICAGO Dad Hat
likbatonboot
$21.41
$25.19
(15% off)
Chicago Bean - Windy City - Travel Dad Hat
taylorvinyls
$21.41
$25.19
(15% off)
Chicago Women’s Basketball Skyline Emblem Blue Gold Sports Design Baseball Cap
TKOprintdesigns
$18.47
$23.09
(20% off)
Chicago Retro 80s Skyline Dad Hat
Dhenin Studio
$19.62
$23.09
(15% off)
Illinois Tortie — Deep Dish Chicago Humor Gift Baseball Cap
Martin's_Design
$20.15
$25.19
(20% off)
Chicago Vintage USA Flag Emblem Badge Art Baseball Cap
PlanetEye Designs
$20.15
$25.19
(20% off)
Lewy City - Chicago - Windy City Dad Hat
RDproject
$21.41
$25.19
(15% off)
Soldier Field Vintage Ticket Shirt Chicago Football Club Retro Stadium Design Baseball Cap
GhostDawgs
$22.67
$28.34
(20% off)
Chicago Skyline Abstract Geometric Mid Century Modern Baseball Cap
k3rstman1
$20.15
$25.19
(20% off)
One Last Hot Sauce Stacey Basketball Farewell Tribute Baseball Cap
b3ida-zl
$18.47
$23.09
(20% off)
Chicago Skyline Minimalist Blue Line Art Dad Hat
BoringClothes
$20.52
$24.14
(15% off)
Chicago The Windy City Minimalist Art Design Baseball Cap
BoringClothes
$19.31
$24.14
(20% off)
312 Chicago Illinois Minimalist Area Code Dad Hat
Paper Drip
$20.52
$24.14
(15% off)
Chicago Baseball Cap
JonysCreativeDesigns
$21.83
$27.29
(20% off)
Chicago Hot Dog No Ketchup L Train Badge Dad Hat
Lyfeinsights
$21.41
$25.19
(15% off)
Chicago Baseball Cap
OlympicsMerch
$20.15
$25.19
(20% off)
Chicago Dad Hat
OlympicsMerch
$21.41
$25.19
(15% off)
Chicago Dad Hat
OlympicsMerch
$21.41
$25.19
(15% off)
Chicago Cribs Baseball Cap
tronephotoworks
$19.98
$24.98
(20% off)
Chicago City Neon Bean Skyline Ferris Wheel Holographic Script Art Baseball Cap
DERA RAY
$18.47
$23.09
(20% off)
Chicago Hockey Warrior Crest | Vintage Hockey Fan Logo Design Baseball Cap
TKOprintdesigns
$18.47
$23.09
(20% off)
Windy City Defensive Legend No. 54 Baseball Cap
Thogan0416
$18.81
$23.51
(20% off)
Windy City Defensive Legend No. 54 – Retro 2000s Football Linebacker Art Dad Hat
Thogan0416
$19.98
$23.51
(15% off)
Chicago, IL License Plate Dad Hat
Lone Frog
$21.41
$25.19
(15% off)
Through Every Hard Winter This Neighborhood Still Knows How To Love - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
Through Every Hard Winter This Neighborhood Still Knows How To Love - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
Through Every Hard Winter This Neighborhood Still Knows How To Love - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
They Only Show The Headlines But We Live The Whole Story - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
They Only Show The Headlines But We Live The Whole Story - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
They Only Show The Headlines But We Live The Whole Story - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
Every Porch Has A Story - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
Every Porch Has A Story - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
Every Porch Has A Story - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
Love Lives On These Corners Too - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
Love Lives On These Corners Too - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
Love Lives On These Corners Too - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
The City Made Us The Block Kept Us - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
The City Made Us The Block Kept Us - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
The City Made Us The Block Kept Us - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
Built From The Block Up - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
Built From The Block Up - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
Built From The Block Up - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
We Look Out For Our Own - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
We Look Out For Our Own - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
We Look Out For Our Own - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
Home Is A Verb Here - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
Home Is A Verb Here - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
Home Is A Verb Here - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
The Block Raised Me - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
The Block Raised Me - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
The Block Raised Me - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
South Side Forever - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
South Side Forever - The Chi Art Dad Hat
dsxclothing
$21.39
$25.17
(15% off)
South Side Forever - The Chi Art Baseball Cap
dsxclothing
$20.13
$25.17
(20% off)
Clark Cartoon | Windy City Baseball Cap
Pandora´s Box
$20.15
$25.19
(20% off)
Chicago Bears | Clark Dad Hat
Pandora´s Box
$21.41
$25.19
(15% off)
Here Comes The Bull - Fierce Red and Black Mascot Illustration Dad Hat
Canache
$21.41
$25.19
(15% off)
Vintage 70s Wellington The Windy City Retro Baseball Cap
DuckOddity
$20.15
$25.19
(20% off)
Funny Kiwi Bird Blown Umbrella Windy Wellington Baseball Cap
DuckOddity
$20.15
$25.19
(20% off)
Minimalist Wellington Cable Car Wind Line Art Baseball Cap
DuckOddity
$20.15
$25.19
(20% off)
Chicago post card Dad Hat
sabinako
$19.62
$23.09
(15% off)
Cute Illinois Map Character - Kawaii Prairie State City Art Baseball Cap
Travel.Art
$18.47
$23.09
(20% off)
Wellington New Zealand Vintage Travel Cable Car Baseball Cap
k3rstman1
$20.15
$25.19
(20% off)
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