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Windy City Caps
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1000+ items
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1000+ items
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Cool Bear Chicago Streetwear Graphic Tee Baseball Cap
NaviSilvas2001
$22.50
$28.13
(20% off)
TBT: Chicago The Bean – Vintage Pop Art Travel Souvenir Baseball Cap
ByJeffro
$18.47
$23.09
(20% off)
We Love Chicago Baseball Clark the Cub Dad Hat
GhostDawgs
$22.30
$26.24
(15% off)
Lou Mitchell's Chicago Streetscape with Willis Tower and Neon Sign Dad Hat
Aryabek
$23.73
$27.92
(15% off)
Lou Mitchell's Chicago Diner with Willis Tower City Landmark Dad Hat
Aryabek
$23.73
$27.92
(15% off)
Oze Maki Fire Force Orange Uniform Against Dramatic Sunset Rooftop Baseball Cap
SolenneAzur
$25.19
$31.49
(20% off)
City Life — Chicago Dad Hat
New-Blood
$19.62
$23.09
(15% off)
Chicago Skyline Retro Sunset Graphic Baseball Cap
DonaldDye64831
$25.19
$31.49
(20% off)
Chicago Football Windy City Retro Graphic Baseball Cap
JenniferW42443
$25.19
$31.49
(20% off)
Redline Charge Chicago Bull Basketball Mascot Dynamic Art Baseball Cap
Pandora´s Box
$20.15
$25.19
(20% off)
Vintage Chicago Football Graphic - Retro Windy City Bear Athletic Gridiron Design | Best Buy Baseball Cap
FisnikR
$27.87
$34.84
(20% off)
Funny Chicago Football Bear Graphic | Windy City Sports Fan Humor | Best Gift Baseball Cap
FisnikR
$27.87
$34.84
(20% off)
Windy City Football Vintage Mascot Retro Sports Fan Art | Perfect Gift For You And Friends Baseball Cap
FisnikR
$27.87
$34.84
(20% off)
Windy City Football Vintage Retro Distressed Graphic Design For Chicago Sports Fans And Gridiron Enthusiasts | Limited Edition Baseball Cap
FisnikR
$27.87
$34.84
(20% off)
Chicago Football North Champions - Windy City Bear Pride & Victory | Best Buy Dad Hat
FisnikR
$29.62
$34.84
(15% off)
Awesome Chicago Baseball Fan Design - South Side Windy City Sports Graphic | ⭐⭐⭐⭐⭐ Baseball Cap
FisnikR
$27.87
$34.84
(20% off)
Chicago Gridiron Bear Mascot Art - Windy City Football Pride & Fan Apparel | ⭐⭐⭐⭐⭐ Best Seller Dad Hat
Astro Cats Social Club
$29.62
$34.84
(15% off)
Haunted Houses Baseball Cap
clarkfraser
$23.51
$29.39
(20% off)
Chicago Bear Cool Sunglasses City Pride Sketch Dad Hat
Snyder93
$21.40
$25.19
(15% off)
Chicago Football, Football Bear Dad Hat
RebeltouilleArt
$23.32
$27.43
(15% off)
Windy City Gridiron Fan Apparel | Best Gift Baseball Cap
Astro Cats Social Club
$27.87
$34.84
(20% off)
Chicago Football Fan - Navy Orange Bear Spirit Design | ⭐⭐⭐⭐⭐ Best Seller Baseball Cap
Astro Cats Social Club
$27.87
$34.84
(20% off)
Chicago Baseball Cap
jadynbennionv
$20.15
$25.19
(20% off)
Chicago Football Vintage Retro Helmet Baseball Cap
BobbyTate64654
$25.27
$31.59
(20% off)
Vintage Chicago Skyline Illinois Adventure Baseball Cap
T-Motive
$18.47
$23.09
(20% off)
Wrigleyville Chicago Baseball Baseball Cap
cuvavirtuex
$20.15
$25.19
(20% off)
Ivy Territory Chicago Baseball Bear Mascot Vintage Art Dad Hat
Pandora´s Box
$21.41
$25.19
(15% off)
Cubs Baseball Cap
markeytaggw
$20.15
$25.19
(20% off)
Cubs Stacked Typography Baseball Fan Baseball Cap
markeytaggw
$20.15
$25.19
(20% off)
Vintage Chicago Basketball Champions Graphic | Retro Chicago Hoops Championship Art | Best Buy Baseball Cap
jennaamichelle
$27.87
$34.84
(20% off)
Chicago Music Blues Great Lakes City Skyline Badge Baseball Cap
RDproject
$20.15
$25.19
(20% off)
Chicago Football Victory Navy And Orange City Pride - Midwest Gridiron Champions Design | ⭐⭐⭐⭐⭐ Baseball Cap
FisnikR
$27.87
$34.84
(20% off)
Chicago Deep Dish Pizza Skyline Foodie Souvenir Badge Dad Hat
RDproject
$21.41
$25.19
(15% off)
The Windy City NFL Football Chicago Illinois Bears Caleb Williams, Obama, Mike Ditka Dad Hat
Space Ghettos
$19.62
$23.09
(15% off)
NFL Football Player QB Chicago Bears Star Caleb Williams NCAA Oklahoma USC Dad Hat
Space Ghettos
$19.62
$23.09
(15% off)
Windy City Football Division Champions 2024 Retro Vintage Style Design For Loyal Chicago Sports Fans | ⭐⭐⭐⭐⭐ Baseball Cap
FisnikR
$27.87
$34.84
(20% off)
Windy City Football Vintage Style Retro Gridiron Fan Art | ⭐⭐⭐⭐⭐ Best Seller Dad Hat
FisnikR
$29.62
$34.84
(15% off)
Chicago Football Spirit | Perfect Gift For You And Friends Dad Hat
FisnikR
$29.62
$34.84
(15% off)
Windy City Football Fan Vintage Retro Distressed Graphic Design For Chicago Sports Enthusiasts | Best Gift Baseball Cap
FisnikR
$27.87
$34.84
(20% off)
Chicago Illinois Urban Population Map Retro Aesthetic Graphic Design | Limited Edition Baseball Cap
TzmMedia
$27.87
$34.84
(20% off)
Chicago Bears Football Mascot Windy City Graphic | Limited Edition Baseball Cap
FisnikR
$27.87
$34.84
(20% off)
Windy City Football Legacy Vintage Retro Sports Aesthetic Design | ⭐⭐⭐⭐⭐ Baseball Cap
FisnikR
$27.87
$34.84
(20% off)
Monsters of the Midway Bear Mascot Soldier Field Vintage Dad Hat
Pandora´s Box
$21.41
$25.19
(15% off)
Windy City Football Heritage Retro Blue And Orange Professional Gridiron Fan Art | ⭐⭐⭐⭐⭐ Best Seller Dad Hat
Astro Cats Social Club
$29.62
$34.84
(15% off)
Vintage Windy City Football Retro Distressed Athletic Apparel Classic Gridiron Heritage Graphic Design | ⭐⭐⭐⭐⭐ Best Seller Dad Hat
Astro Cats Social Club
$29.62
$34.84
(15% off)
Good Better Best Chicago Football Fan Art | Windy City Sports Pride Graphic | ⭐⭐⭐⭐⭐ Best Seller Baseball Cap
Astro Cats Social Club
$27.87
$34.84
(20% off)
Chicago Gridiron Warrior Mascot Design | Perfect Gift For You And Friends Baseball Cap
Astro Cats Social Club
$27.87
$34.84
(20% off)
Windy City Football Vintage Retro Style Illustration For Chicago Sports Fans And Gridiron Lovers | Best Buy Baseball Cap
Astro Cats Social Club
$27.87
$34.84
(20% off)
Chicago Football Good Better Best Vintage Sports Design | ⭐⭐⭐⭐⭐ Baseball Cap
Astro Cats Social Club
$27.87
$34.84
(20% off)
Windy City Gridiron Football Heritage Vintage Style Sports Fan Graphic Design | Perfect Gift For You And Friends Baseball Cap
MGOE
$27.87
$34.84
(20% off)
Chicago Football Fan Navy Orange City Pride | Windy City Game Day Sports Aesthetic | ⭐⭐⭐⭐⭐ Dad Hat
FisnikR
$29.62
$34.84
(15% off)
Vintage Chicago Football Game Day Cheerleader Style Retro Windy City Sports Aesthetic Graphic | Perfect Gift For You And Friends Baseball Cap
FisnikR
$27.87
$34.84
(20% off)
Chicago Christmas Retro Holiday Souvenir Plate Baseball Cap
The Souvenir Dept.
$20.15
$25.19
(20% off)
Chicago Christmas Vintage License Plate Dad Hat
The Souvenir Dept.
$23.19
$27.29
(15% off)
Chicago Football Fan Art | Best Gift Dad Hat
Junkers
$29.62
$34.84
(15% off)
Windy City Gridiron Champions - Football Fan Apparel | Best Buy Dad Hat
Junkers
$29.62
$34.84
(15% off)
Windy City Football Pride Retro Vintage Style Graphic Design For Chicago Sports Fans And Gridiron Enthusiasts | Limited Edition Dad Hat
Junkers
$29.62
$34.84
(15% off)
Chicago Windy City Pattern Dad Hat
TinyWeird
$21.41
$25.19
(15% off)
Windy City Football Fan Christmas Design - Festive Holiday Spirit | Best Gift Baseball Cap
Astro Cats Social Club
$24.35
$30.44
(20% off)
Retro Chicago Football Fan Apparel | Best Buy Dad Hat
Astro Cats Social Club
$25.87
$30.44
(15% off)
Chicago Bears Nfc North Champs | Best Gift Dad Hat
Astro Cats Social Club
$25.87
$30.44
(15% off)
Windy City Football Pride Retro Orange And Navy Vintage Style Graphic | Best Buy Dad Hat
Astro Cats Social Club
$25.87
$30.44
(15% off)
Windy City Football Fan Pride - Classic Navy Orange Design | Best Gift Dad Hat
Astro Cats Social Club
$25.87
$30.44
(15% off)
Chicago Dreams – The Windy City Dad Hat
RockitBaby
$21.41
$25.19
(15% off)
Chicago Baseball Fan Gear & Apparel | ⭐⭐⭐⭐⭐ Best Seller Baseball Cap
Jmkdesigner
$24.35
$30.44
(20% off)
Chicago Football Fan Gear | ⭐⭐⭐⭐⭐ Dad Hat
Peve1728
$25.87
$30.44
(15% off)
Chicago Football Iceman - Cool Under Pressure Windy City Qb Gridiron Sports Art | Limited Edition Dad Hat
Arnolmendis
$27.65
$32.54
(15% off)
Ghostface-Chicago-Football Number 34 Sweetness Inspired Skyline Graphic Baseball Cap
DYALEEZ-XCR
$19.98
$24.98
(20% off)
City Of Chicago Founded In 1837 Sears Willis Tower Dad Hat
jeshands
$20.52
$24.14
(15% off)
Vintage Windy City Basketball Athletic Crest Art Dad Hat
BlasiseDS
$19.62
$23.09
(15% off)
Vibrant Chicago Basketball Bull Graffiti Typography Graphic Dad Hat
BlasiseDS
$19.62
$23.09
(15% off)
Chicago Urban Street Art – Windy City Graffiti Skyline Dad Hat
URBIVO
$21.41
$25.19
(15% off)
Chicago Basketball City Skyline Urban Streetwear Graphic Dad Hat
BlasiseDS
$19.62
$23.09
(15% off)
Chicago Basketball Skyline Crest Vintage Graphic Baseball Cap
BlasiseDS
$18.47
$23.09
(20% off)
Chicago Minimalistic Map Art Baseball Cap
MapsNerd
$19.64
$24.56
(20% off)
Chicago Sporty Beagle Retro Cartoon Dog Art | ⭐⭐⭐⭐⭐ Dad Hat
teesforteens
$25.87
$30.44
(15% off)
Chicago Football Vintage Helmet Retro Dad Hat
AlejandreEd
$24.08
$28.34
(15% off)
Chicago Vibes Collage Retro Travel City Dad Hat
GaryGibbs36288
$26.85
$31.59
(15% off)
Chicago Retro Football EST 1920 Graphic Dad Hat
degasperis
$23.91
$28.13
(15% off)
Chicago Football Retro Vintage Style Dad Hat
MasonWill19865
$26.85
$31.59
(15% off)
Vintage Chicago Football Fan Baseball Cap
eLograsso
$20.15
$25.19
(20% off)
Cute Cartoon Beagle Playing Chicago Baseball - Windy City Fan Art | Best Gift Dad Hat
Made-easy
$25.87
$30.44
(15% off)
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