Chicago Style Caps

869 items

Deep Dish, Deep Loyalty Baseball Cap

chicagocap

$23.09

Did You Just Look At My Wiener? Chicago Style Hot Dog Graphic Dad Hat

ThreadRiotTees

$25.19

Ray's Music Exchange Shirt | Vintage Chicago Music Store Tee | Retro Music Lover Gift Baseball Cap

GarnerSupplyCo

$25.19

Chicago Fire Retro Action Drama Firehouse 51 Severide Casey Tribute Art TV Show Poster Dad Hat

Art's Diner

$23.09

Chicago PD Retro Crime Drama Intelligence Unit Hank Voight Tribute Art TV Show Poster Baseball Cap

Art's Diner

$23.09

Chicago Med Retro Medical Drama Emergency Room Hospital Tribute Art TV Show Poster Dad Hat

Art's Diner

$23.09

I Just Came For The Wieners-Chicago Style Hot Dog Baseball Cap

ThreadRiotTees

$25.19

Bad Day To Be A Hot Dog Funny Shirt Dad Hat

TeNovaStudio

$24.14

Chicago Graffiti Street Art Baseball Cap

GraffiCity

$24.56

Illinois is Home - Vintage Distressed Red Stamp Dad Hat

chaaval

$25.19

Golden Chicago Rare Japanese Kanji Calligraphy Funny Windy City Gift Art Dad Hat

noworries-art

$23.09

Chicago Style Rebel Baseball Cap

HillC1985

$23.09

One Choice Can Transform You. – Divergent Fine Art Print Dad Hat

Art's Diner

$23.09

Justice Has a New Face – Above the Law Fine Art Print Baseball Cap

Art's Diner

$23.09

Vintage Field Style Crest Emblem Dad Hat

Kartezartion

$25.19

chicago baseball retro stripes Dad Hat

LuloCreative

$27.29

The Heist of Their Lives – Widows Fine Art Print Dad Hat

Art's Diner

$23.09

Road Trip Quote Graphic Stylized Print Baseball Cap

msolgray

$25.19

Stacey King Tribute Baseball Cap

HishuClothing

$25.19

Stacey King Tribute Dad Hat

BerryHand

$25.19

Iconic Chicago Architecture Meets Deep Dish Dad Hat

BoringClothes

$24.14

Chicago Deep Dish Pizza Lover Graphic Baseball Cap

BoringClothes

$24.14

Hot Dog Summer Dad Hat

vibeno1

$26.22

Whimsical deer graffiti art Dad Hat

TinkerUnion369

$23.09

Chicago Hot Dog No Ketchup L Train Badge Baseball Cap

Lyfeinsights

$25.19

Vintage Blue Red Baseball Club Classic T-Shirt Dad Hat

Lilbahlil

$25.19

Never Ketchup Frankfurter Flexing Muscles Chicago hot dog Dad Hat

snowry

$24.14

Crime Story Poster – Dennis Farina 1960s Mob Drama Dad Hat

Art's Diner

$23.09

Chicago Bears Football Graphic Decal Design Baseball Cap

socialarmour

$27.29

Chicago Retro Basketball Broken Chain Hoop Baseball Cap

FlashCraft Design

$25.19

Count Dante - The Deadliest Man Alive Dad Hat

AestheticNow

$23.09

1968 Psychedelic Political Protest Poster Art Dad Hat

DuckOddity

$25.19

Chicago Style Hot Dog Urban Foodie Emblem Dad Hat

snowry

$24.14

Hotdog Heros Chicago Dog Dad Hat

1mooreroy

$23.09

Chicago style hot dog Baseball Cap

The King's general goods

$28.34

Chicago Skyline Vintage Retro City Illustration Baseball Cap

Andruzito

$25.19

Illinois State Print Logo / Illinois Pride Baseball Cap

Thehatinthecat

$27.29

Im From Chicago Please Act Accordingly Funny City Pride Design Dad Hat

kiralynstration

$27.29

The Fugitive: I Didn't Kill My Wife! Baseball Cap

Art's Diner

$23.09

Kanye-West-Spectrum-Upsurge - Ye in a Black Suit Holding a Wine Glass Baseball Cap

ZERO-MIND

$25.19

The Chicago Heiress Baseball Cap

CHRIST5000

$25.19

Chicago Hot Dog Flag Style City Foodie Emblem Dad Hat

snowry

$24.14

Windy City Hot Dog Flag Chicago Style Wiener Dad Hat

snowry

$24.14

Chicago Flag Foodie Skyline Distressed Style Dad Hat

snowry

$24.14

Capone: King of Chicago Baseball Cap

Art's Diner

$23.09

Illinois Vintage Skyline Retro State Design Baseball Cap

StateMoodDesigns

$23.09

Ye in a Black Suit Holding a Wine Glass - Hip Hop Icon (full color) Dad Hat

ZERO-MIND

$25.19

The Untouchables: Never Stop Fighting 'Til The Fight Is Done Baseball Cap

Art's Diner

$23.09

Ye in a Black Suit Holding a Wine Glass - Alienated Hip Hop Icon Dad Hat

ZERO-MIND

$25.19

Chicago Skyline – Graffiti Style T-Shirt Design - USA Travel City Art Baseball Cap

Earth Celebration Designs

$27.29

Chicago Raccoon Hot Dog Beanie City Lover Baseball Cap

snowry

$24.14

Iceman Quarterback Frost Edition Football Shirt Dad Hat

TheClockOutClub

$23.09

The Sting: The Big Con Dad Hat

Art's Diner

$23.09

Chicago: Razzle Dazzle Em’ Baseball Cap

Art's Diner

$23.09

Angry Blue Bear Baseball Player Sports Mascot Dad Hat

Pandora´s Box

$25.19

Chicago Basketball Vintage Shirt – Red Black Skyline Hoops Badge Tee Baseball Cap

TKOprintdesigns

$23.09

The Weiner Pit Hot Dog Stand Dad Hat

Milhouse602

$23.09

The Grant Park Connection: Broadstroke 80s Tribute Baseball Cap

Art's Diner

$23.09

SUNSHINE IN MY BONES Dad Hat

ZenRave Designs

$25.19

Pope Leo American Flag - Pope Leon - Pope Leon XIV 2026 – Chicago’s First American Pope Design Dad Hat

FerminVigo

$25.19

Chicago Hot Dog Summer Style 4Th Of July No Ketchup Dad Hat

SyncSusscess

$25.19

Chicago Handshake Beer Lover Drinking Fans Baseball Cap

Dressed For Duty

$25.19

Item preview, Pope Leo - White Sox Pope - Da Pope - Team Pope Leo XIV- Pope Leon XIV 2026 – Chicago’s First American Pope Design designed and sold by William-Do-X.

Pope Leo - White Sox Pope - Da Pope - Team Pope Leo XIV- Pope Leon XIV 2026 – Chicago’s First American Pope Design Dad Hat

William-Do-X

$25.19

Pope Leo - Da Pope - Team Pope Leo XIV- Pope Leon XIV 2026 – Chicago’s First American Pope Design Dad Hat

William-Do-X

$25.19

Pope Leo - Pope Leo Pope America - Pope Leon XIV 2026 – Chicago’s First American Pope Design Baseball Cap

William-Do-X

$25.19

Item preview, Pope Leo - Pope Leo XIV - Pope Leo XIV 10 Vintage - Da Pope - Pope Leon - Pope Leon XIV 2026 – Chicago’s First American Pope Design designed and sold by William-Do-X.

Pope Leo - Pope Leo XIV - Pope Leo XIV 10 Vintage - Da Pope - Pope Leon - Pope Leon XIV 2026 – Chicago’s First American Pope Design Baseball Cap

William-Do-X

$25.19

Pope Leo - Da Pope - Pope Leon XIV 2026 – Chicago’s First American Pope Design Dad Hat

William-Do-X

$25.19

Pope Leo - Da Pope - Pope Leon XIV 2026 – Chicago’s First American Pope Design Dad Hat

William-Do-X

$25.19

Item preview, Pope Leo XIV - Pope Leo XIV 10 Vintage - Da Pope - Pope Leon - Pope Leon XIV 2026 – Chicago’s First American Pope Design designed and sold by William-Do-X.

Pope Leo XIV - Pope Leo XIV 10 Vintage - Da Pope - Pope Leon - Pope Leon XIV 2026 – Chicago’s First American Pope Design Baseball Cap

William-Do-X

$25.19

Pope Leo XIV 10 Vintage - Da Pope - Pope Leon - Pope Leon XIV 2026 – Chicago’s First American Pope Design Dad Hat

William-Do-X

$25.19

Pope Leo American Flag - Pope Leon - Pope Leon XIV 2026 – Chicago’s First American Pope Design Baseball Cap

William-Do-X

$25.19

Pope Leo - Chicago Proud - Pope Leon XIV 2026 – Chicago’s First American Pope Design Baseball Cap

William-Do-X

$25.19

Pope Leo Pope America - Pope Leo - Pope Leon XIV 2026 – Chicago’s First American Pope Design Dad Hat

William-Do-X

$25.19

Pope Chicago - Pope Leo - Pope Leon XIV 2026 – Chicago’s First American Pope Design Dad Hat

William-Do-X

$25.19

I Stand With Pope Leo - Chicago Proud - Pope Leon XIV 2026 – Chicago’s First American Pope Design Baseball Cap

William-Do-X

$25.19

Da Pope - Pope Leon XIV 2026 – Chicago’s First American Pope Design Baseball Cap

William-Do-X

$25.19

Da Pope Trump Pope Burger - Pope Leon XIV 2026 – Chicago’s First American Pope Design Baseball Cap

William-Do-X

$25.19

Da Pope Trump Jesus Da Pope - Pope Leon XIV 2026 – Chicago’s First American Pope Design Dad Hat

William-Do-X

$25.19

Da Pope Leo XIV Trump Jesus Humor - Pope Leon XIV 2026 – Chicago’s First American Pope Design Baseball Cap

William-Do-X

$25.19

Item preview, Da Pope From America Chicago Pope Leo XIV Provost - Pope Leon XIV 2026 – Chicago’s First American Pope Design designed and sold by William-Do-X.

Da Pope From America Chicago Pope Leo XIV Provost - Pope Leon XIV 2026 – Chicago’s First American Pope Design Baseball Cap

William-Do-X

$25.19

Da Pope - Chicago Proud - Pope Leon XIV 2026 – Chicago’s First American Pope Design Dad Hat

William-Do-X

$25.19

Item preview, Vintage Chicago Baseball Comiskey Park Shirt, Retro Stadium Tee, Classic Ballpark Design, White Sox Era Inspired designed and sold by GhostDawgs.

Vintage Chicago Baseball Comiskey Park Shirt, Retro Stadium Tee, Classic Ballpark Design, White Sox Era Inspired Dad Hat

GhostDawgs

$26.24

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Chicago Style Caps

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