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Chicago Flag Caps
757 items
Hats
Filters (2)
757 items
Newest
Sox Script Over Distressed American Flag Dad Hat
kayeufriday
$21.41
$25.19
(15% off)
Chicago Neighborhoods Baseball Cap
CMooreWorx
$20.48
$25.61
(20% off)
CM Punk Chicago Flag Fist Best In The World Dad Hat
Sedwalhissan
$21.41
$25.19
(15% off)
America 250 Chicago Windy City T-Shirt | Patriotic Skyline 1776-2026 Semiquincentennial Tee v4 Dad Hat
DarylWelsh2024
$23.19
$27.29
(15% off)
America 250 Chicago Windy City T-Shirt | Patriotic Skyline 1776-2026 Semiquincentennial Tee v3 Baseball Cap
DarylWelsh2024
$21.83
$27.29
(20% off)
America 250 Chicago Windy City T-Shirt | Patriotic Skyline 1776-2026 Semiquincentennial Tee v2 Baseball Cap
DarylWelsh2024
$21.83
$27.29
(20% off)
America 250 Chicago Windy City T-Shirt | Patriotic Skyline 1776-2026 Semiquincentennial Tee v1 Dad Hat
DarylWelsh2024
$23.19
$27.29
(15% off)
Chicago Flag Typography – Vintage City Pride Design Dad Hat
SimplyJasper
$21.94
$25.82
(15% off)
Chicago Skyline Hand Drawing - Travel Souvenir - South Side Chicago - Sears Willis Tower Baseball Cap
HoganHandmade
$18.47
$23.09
(20% off)
Jewels Dad Hat
Illannoyed
$20.69
$24.35
(15% off)
Chicago Rebel Dad Hat
HillC1985
$19.62
$23.09
(15% off)
Chicago Flag Inspired Stars and Stripes Dad Hat
chicagocap
$19.62
$23.09
(15% off)
Retro Illinois Chicago Skyline Flat Vector Travel Baseball Cap
Paper Drip
$19.31
$24.14
(20% off)
Retro Illinois Chicago Skyline Flat Vector Travel Baseball Cap
Paper Drip
$19.31
$24.14
(20% off)
Retro Illinois Chicago Skyline Flat Vector Travel Dad Hat
Paper Drip
$20.52
$24.14
(15% off)
Illinois Flag Initials IL Dad Hat
shitpostee
$23.19
$27.29
(15% off)
Illinois Circle Flag IL Baseball Cap
shitpostee
$21.83
$27.29
(20% off)
Northwest Indiana Flag -The Region Flag - NWI Logo T-Shirt Baseball Cap
HoganHandmade
$18.47
$23.09
(20% off)
Illinois Flag IL Dad Hat
shitpostee
$23.19
$27.29
(15% off)
Vintage Cubs American Flag Graphic Patriotic USA Baseball Inspired Retro Dad Hat
PerfectMatch
$22.30
$26.24
(15% off)
POLISH AMERICAN ONE HEART • TWO FLAGS Dad Hat
GraphicGlowTeesStore
$19.62
$23.09
(15% off)
Chicago, Illinois Baseball Cap
Felipithecus
$20.15
$25.19
(20% off)
Chicago Vintage USA Flag Emblem Badge Art Baseball Cap
PlanetEye Designs
$20.15
$25.19
(20% off)
Illinois State Shape Flag IL Dad Hat
shitpostee
$23.19
$27.29
(15% off)
Pride Flag Baseball Cap
ArtitudePrintLb
$20.15
$25.19
(20% off)
Chicago, Illinois Dad Hat
DeadXIII
$19.62
$23.09
(15% off)
Chicago, Illinois Dad Hat
DeadXIII
$19.62
$23.09
(15% off)
Illinois 250th Anniversary Celebration State Pride Dad Hat
No Limits T-Shirts
$19.62
$23.09
(15% off)
Chicago The Windy City Minimalist Art Design Baseball Cap
BoringClothes
$19.31
$24.14
(20% off)
Chicago Dad Hat
JonysCreativeDesigns
$23.19
$27.29
(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)
Illinois Flag Baseball Cap
youngVl
$18.47
$23.09
(20% off)
Illinois Heart IL Baseball Cap
shitpostee
$21.83
$27.29
(20% off)
Distressed Illinois State Flag IL Baseball Cap
shitpostee
$21.83
$27.29
(20% off)
Illinois State Flag IL Dad Hat
shitpostee
$23.19
$27.29
(15% off)
Vintage USA Cities Patriotic American Flag Travel Design Baseball Cap
reanacreations
$18.47
$23.09
(20% off)
Chicago post card Dad Hat
sabinako
$19.62
$23.09
(15% off)
Hum Baseball Cap
B4CKM4N
$18.47
$23.09
(20% off)
Bucktown Dad Hat
Normbot2000
$19.62
$23.09
(15% off)
Chicago Dad Hat
OlympicsMerch
$21.41
$25.19
(15% off)
Chicago Pizza Slices Distressed Flag Design Baseball Cap
snowry
$19.31
$24.14
(20% off)
Chicago Flag Four Stars City Pride Illinois Dad Hat
snowry
$20.52
$24.14
(15% off)
Chicago Flag Skyline City Pride Dad Hat
snowry
$20.52
$24.14
(15% off)
Chicago Style Hot Dog Urban Foodie Emblem Dad Hat
snowry
$20.52
$24.14
(15% off)
Chicago Hot Dog Flag Parody Dad Hat
snowry
$20.52
$24.14
(15% off)
Chicago Flag Food Icons Skyline Bean City Dad Hat
snowry
$20.52
$24.14
(15% off)
Distressed Chicago Flag Foodie Skyline Baseball Cap
snowry
$19.31
$24.14
(20% off)
Chicago Skyline City Flag Pride Urban Design Dad Hat
snowry
$20.52
$24.14
(15% off)
Chicago Hot Dog Flag Style City Foodie Emblem Baseball Cap
snowry
$19.31
$24.14
(20% off)
Windy City Hot Dog Flag Chicago Style Wiener Dad Hat
snowry
$20.52
$24.14
(15% off)
Chicago City Icons Flag Hot Dog Pizza Bean Baseball Cap
snowry
$19.31
$24.14
(20% off)
Chicago Flag Foodie Skyline Distressed Style Dad Hat
snowry
$20.52
$24.14
(15% off)
Chicago Pizza Flag Slices Design Baseball Cap
snowry
$19.31
$24.14
(20% off)
Chicago Pizza Flag Distressed Foodie Apparel Baseball Cap
snowry
$19.31
$24.14
(20% off)
Chicago City Flag Iconic Symbol Design Baseball Cap
snowry
$19.31
$24.14
(20% off)
Cubs Win W Flag – Wrigley Field Sign Mascot Retro Graphic Dad Hat
carolineduvivier
$21.41
$25.19
(15% off)
The Greatest Game Ever Played Baseball Cap
NinigFox
$20.15
$25.19
(20% off)
Chicago Raccoon Hot Dog Beanie City Lover Baseball Cap
snowry
$19.31
$24.14
(20% off)
Retriever Chicago Flag Beanie Dog Baseball Cap
snowry
$19.31
$24.14
(20% off)
Chicago Flag Beanie Tabby Cat Dad Hat
snowry
$20.52
$24.14
(15% off)
Chicago Flag Baseball Cap
BraydenHafner
$18.47
$23.09
(20% off)
Chicago Flag Baseball Jersey Mesh Edition Baseball Cap
Cestus
$17.63
$22.04
(20% off)
coloring book town Baseball Cap
B4CKM4N
$18.47
$23.09
(20% off)
Pope Leo American Flag - Pope Leon - Pope Leon XIV 2026 – Chicago’s First American Pope Design Dad Hat
FerminVigo
$21.41
$25.19
(15% off)
Pope Leo American Flag - Pope Leon - Pope Leon XIV 2026 – Chicago’s First American Pope Design Dad Hat
William-Do-X
$21.41
$25.19
(15% off)
Chicago USA Linocut Style Baseball Cap
Thistle-TShop
$20.15
$25.19
(20% off)
Chicago Rusty But Trusty Oldsmobile Cutlass Supreme Baseball Cap
Cat Haven & Rescue
$18.47
$23.09
(20% off)
Chicago Flag - Windy City Pride & Illinois Urban Heritage Baseball Cap
NTGUILTY
$20.15
$25.19
(20% off)
Illinois State Flag - Land of Lincoln & Prairie Pride Heritage Baseball Cap
NTGUILTY
$20.15
$25.19
(20% off)
Chicago – Windy City Travel & Tourism Guide | Millennium Park, Navy Pier, Museum Campus, Architecture, Riverwalk & Attractions Baseball Cap
Typologystudios
$20.99
$26.24
(20% off)
Chicago Irish Dad Hat
Lone Frog
$21.41
$25.19
(15% off)
Chicago Irish Baseball Cap
Lone Frog
$20.15
$25.19
(20% off)
WGUSA Clothing © Unisex 饥饿的 Dad Hat
Present U.S.
$19.62
$23.09
(15% off)
WGUSA Clothing © 反叛 Baseball Cap
Present U.S.
$18.47
$23.09
(20% off)
Chicago, USA Dad Hat
PaulSDesign
$19.62
$23.09
(15% off)
Chicago 1833 Windy City Pride Dad Hat
NoulDesign
$19.62
$23.09
(15% off)
Illinois Dad Hat
JonysCreativeDesigns
$23.19
$27.29
(15% off)
Hockey Chicago Blackhawks Chicago Flag Baseball Cap
Ubuntu Arts
$20.15
$25.19
(20% off)
Chicago Flag With Teams Dad Hat
Hamedmohamed
$21.41
$25.19
(15% off)
Chicago Flags With Teams And Skyline Baseball Cap
GG4NDII
$20.15
$25.19
(20% off)
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