Chicago Style Caps

1000+ items

Chicago Style Giardiniera Dad Hat

jnedza

$29.39

Item preview, Scottie Pippen Basketball Legend Chicago Signature Vintage Retro 80s 90s Bootleg Rap Style designed and sold by Isabella Heller ⭐⭐⭐⭐⭐(316).

Scottie Pippen Basketball Legend Chicago Signature Vintage Retro 80s 90s Bootleg Rap Style Baseball Cap

Isabella Heller ⭐⭐⭐⭐⭐(316)

$27.29

Chicago logo circle Baseball Cap

Backstage by Leyzel

$25.19

Chicago North Side Baseball Baseball Cap

sabinako

$23.09

Chicago Style Dad Hat

Shannon Alexis Designs

$36.73

HOUSE MUSIC - Font Style (black) Baseball Cap

Discothreadz

$25.19

Love Chicago Style Baseball Cap

StylesOfLove

$27.29

Chicago Pizza Wave Dad Hat

wojysmokes

$25.19

mike ditka Hope style Baseball Cap

OrlandNienow

$25.19

Chicago Style Hot Dog Baseball Cap

bouquetofstars

$25.19

Chicago Vs Everybody Football Fan Apparel | Limited Edition Baseball Cap

FisnikR

$34.84

Vintage Style Chicago License Plate Baseball Cap

Decal Mania

$26.87

Item preview, Chicago Style Hot Dog Flag | Glizzy Traditional Specific Signature Food Famous No Ketchup Chicago Flag Dog | Chicago Illinois State South Side South Suburbs Depression Sandwich Anthropomorphic Mascot designed and sold by Any Color Designs.

Chicago Style Hot Dog Flag | Glizzy Traditional Specific Signature Food Famous No Ketchup Chicago Flag Dog | Chicago Illinois State South Side South Suburbs Depression Sandwich Anthropomorphic Mascot Dad Hat

Any Color Designs

$27.29

Sometimes I feel like I'm melting Baseball Cap

wojysmokes

$25.19

Item preview, Chicago Style Hot Dog Flag | Glizzy Specific Traditional Signature Food Famous No Ketchup Chicago Flag Dog | Chicago Illinois State South Side South Suburbs Depression Sandwich Anthropomorphic Mascot designed and sold by Any Color Designs.

Chicago Style Hot Dog Flag | Glizzy Specific Traditional Signature Food Famous No Ketchup Chicago Flag Dog | Chicago Illinois State South Side South Suburbs Depression Sandwich Anthropomorphic Mascot Dad Hat

Any Color Designs

$27.29

American Style,Illinois. Baseball Cap

JoyfulCreations

$25.19

Chicago Bean Vintage Style Decal Dad Hat

Decal Mania

$26.88

Chicago Icons: Popcorn Baseball Cap

buhloop

$23.09

Chicago Minimalist Map United States Dad Hat

BoringClothes

$24.14

Chicago Style Hot Dog Dad Hat

dudelinart

$25.19

old style cubs logo Baseball Cap

Sierra & Co

$25.19

Chicago Style Hotdog Baseball Cap

MalignWineArt

$25.19

Chicago bears 80s style Baseball Cap

Ushopfake

$25.19

Soldier Field Pattern Baseball Cap

Dude Stuff

$29.39

Chicago Postcard Style Image Baseball Cap

purplerosemary

$35.68

Wrigley Field Mug Pattern - Available on socks and more Dad Hat

Dude Stuff

$29.39

Chicago Style Pizza Pattern - Pizza - Stadium - Field - license - flag - sears tower - cloud gate Dad Hat

Dude Stuff

$29.39

Chicago Style Hot Dog Dad Hat

carolineduvivier

$25.19

Chicago Skyline Pulse Dad Hat

Dude Stuff

$29.39

Soldier Field ( Chicago Bears ) - Available on socks and more Baseball Cap

Dude Stuff

$29.39

Illinois DMV License Plate and State Flag Pattern Baseball Cap

Dude Stuff

$29.39

Hey Chicago Whadya Say Baseball Hot Dog Retro Baseball Cap

empiric-designs

$23.09

Chicago Skyline, Wes Anderson Style Baseball Cap

Skyline-Design5

$25.19

Chicago Cubbies Baseball Cap

Tara Collins

$23.09

Taste of America, Chicago Style Hotdog Dad Hat

MalignWineArt

$25.19

Chicago Mondrian style poster Baseball Cap

CMYKStudio

$25.19

Chicago Style HotDog Dad Hat

Chicago Style – Funny Hot Dog Lover Baseball Cap

dudelinart

$25.19

Chicago Hot Dog - Chicago Dog Style Dad Hat

luckymooninc

$27.29

1912 Chicago The Summer Resort Dad Hat

historicimage

$27.29

1913 Chicago The Summer Resort Baseball Cap

historicimage

$27.29

Chicago Mondrian style poster 3D Baseball Cap

CMYKStudio

$25.19

Chicago Deep Dish Pizza Dad Hat

AmericanCulinaryCulture

$23.09

Chicago USA Linocut Style Baseball Cap

Thistle-TShop

$25.19

Da Pope! Chicago Style Hot Dog Baseball Cap

BerlinerKatzen

$25.19

1912 Chicago The Summer Resort Dad Hat

historicimage

$27.29

Chicago Style Dad Hat

Illannoyed

$24.35

1912 Chicago The Summer Resort Baseball Cap

historicimage

$27.29

1930 Chicago Has Everything Baseball Cap

historicimage

$27.29

Retro Chicago Baseball Cap

FrictionMaxxing

$25.19

Chicago USA Linocut Style Baseball Cap

Thistle-TShop

$25.19

Chicago, United States of America | Anime style Dad Hat

ComicsFactory

$25.19

Chicago Cloud Gate Windy City Landmark Design Baseball Cap

castillomiami

$26.24

Delicious Chicago Pizza Baseball Cap

harebrained

$25.19

Chicago USA Linocut Style Baseball Cap

Thistle-TShop

$25.19

Chicago USA Linocut Style Dad Hat

Thistle-TShop

$25.19

Chicago Illinois Retro Dad Hat

Oniyasha

$29.39

Michigan Ave Chicago Vintage Style Baseball Cap

Decal Mania

$26.87

Chicago Deep Dish Pizza Lover Graphic Baseball Cap

BoringClothes

$24.14

Chicago Style Hot Dog Beating Up Ketchup Dad Hat

BerlinerKatzen

$25.19

Chicago swiss style poster Dad Hat

CMYKStudio

$25.19

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

Earth Celebration Designs

$27.29

Baseball cubs Baseball Cap

sabinako

$23.09

Historian Sticker: Painstakingly trained in the Chicago Manual of Style Baseball Cap

anthropocynical

$25.19

Chicago | Post-impressionist painting style Dad Hat

i got that dog in me - Chicago Style Baseball Cap

Boxout

$25.19

Urban Streetwear Chicago Trend Baseball Cap

Zuuag

$24.66

Chicago 1833 Windy City Pride Baseball Cap

NoulDesign

$23.09

Urban Streetwear Chicago Trend Dad Hat

Zuuag

$24.66

Chicago House Music Turntable Hot Graffiti Style Dad Hat

idabry

$29.39

Chicago Basketball Retro Style – Windy City Vintage Design Dad Hat

Ancestral-Shop

$23.09

Chicago 2026 Layered Typography Windy City Design Baseball Cap

cabana.space

$25.19

Chicago style hotdog Dad Hat

TavellynArt

$25.19

Chicago Food Department Dad Hat

Illannoyed

$24.35

Chicago Baseball - Ballpark Erupts Baseball Cap

MASMUS27

$22.46

Chicago Illinois License Plate Style Dad Hat

levsal

$24.14

Chilly Bear Chicago Baseball Cap

littlebitmad

$23.09

Chicago Football Vintage Style Dad Hat

hayesuzzia887

$25.19

Item preview, Chicago Style Pizza Flag | Deep Dish Traditional Specific Signature Food Famous Stuffed Chicago Flag Pizza | Chicago Illinois State South Side South Suburbs Square Pizza Anthropomorphic Mascot designed and sold by Any Color Designs.

Chicago Style Pizza Flag | Deep Dish Traditional Specific Signature Food Famous Stuffed Chicago Flag Pizza | Chicago Illinois State South Side South Suburbs Square Pizza Anthropomorphic Mascot Dad Hat

Any Color Designs

$27.29

Chicago Beef Department Dad Hat

Illannoyed

$24.35

Chicago Style Baseball Cap

LimeAnaconda

$25.19

Chicago Logo: Collegiate design with a sporty urban style Baseball Cap

Chicago Football Vintage Style Dad Hat

pruittpeteart

$23.09

Hey Chicago What Do You Say Baseball Cap

carolineduvivier

$25.19

Chicago Stocking Cap Dog with Flag Baseball Cap

dangerhuskie

$25.19

Chicago Logo: Collegiate design with a sporty urban style Dad Hat

AdamShirts7

$24.98

Chicago Travel Illustration Dad Hat

archetype prints

$29.39

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Chicago Style Caps

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