Chicago Style Caps

869 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 Dad Hat

Isabella Heller ⭐⭐⭐⭐⭐(316)

$27.29

Chicago logo circle Dad Hat

Backstage by Leyzel

$25.19

Chicago Style Dad Hat

Shannon Alexis Designs

$36.73

Chicago Flag Foodie Skyline Distressed Style Baseball Cap

snowry

$24.14

HOUSE MUSIC - Font Style (black) Dad Hat

Discothreadz

$25.19

Im From Chicago Please Act Accordingly Funny City Pride Design Baseball Cap

kiralynstration

$25.19

Love Chicago Style Baseball Cap

StylesOfLove

$27.29

Chicago Pizza Wave Dad Hat

wojysmokes

$25.19

Chicago Style Hot Dog Dad Hat

bouquetofstars

$25.19

Vintage Style Chicago License Plate Baseball Cap

Decal Mania

$26.87

Chicago Style in White outline Dad Hat

Stefanie1624

$25.19

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

I REPRESENT CHICAGO - RETRO CITY SUNSET STYLE Baseball Cap

Verasoto

$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

Sometimes I feel like I'm melting Dad Hat

wojysmokes

$25.19

American Style,Illinois. Baseball Cap

JoyfulCreations

$25.19

Chicago Bean Vintage Style Decal Dad Hat

Decal Mania

$26.88

Chicago Icons: Popcorn Dad Hat

buhloop

$23.09

Chicago Style Hot Dog Dad Hat

dudelinart

$25.19

Chicago Style Hotdog Baseball Cap

MalignWineArt

$26.24

Wrigley Field Mug Pattern - Available on socks and more Baseball Cap

Dude Stuff

$29.39

Chicago Style Pizza Pattern - Pizza - Stadium - Field - license - flag - sears tower - cloud gate Baseball Cap

Dude Stuff

$29.39

Chicago Postcard Style Image Dad Hat

purplerosemary

$35.68

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

Dude Stuff

$29.39

Chicago Skyline Pulse Baseball Cap

Dude Stuff

$29.39

Soldier Field Pattern Baseball Cap

Dude Stuff

$29.39

Chicago Style Hot Dog Dad Hat

carolineduvivier

$25.19

Illinois DMV License Plate and State Flag Pattern Baseball Cap

Dude Stuff

$29.39

Chicago Skyline, Wes Anderson Style Baseball Cap

Skyline-Design5

$25.19

Taste of America, Chicago Style Hotdog Dad Hat

MalignWineArt

$26.24

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

The Bandits, Chicago style Dad Hat

Ashact

$25.19

Pittsburgh Chi Style Baseball Cap

jrmclaughlin

$23.09

Chicago Style HotDog Dad Hat

Nanagans

$25.19

Buzz’n Bear Baseball Cap

Illannoyed

$24.45

Chicago Hot Dog - Chicago Dog Style Dad Hat

luckymooninc

$27.29

Chicago Style – Funny Hot Dog Lover Baseball Cap

dudelinart

$25.19

1913 Chicago The Summer Resort Dad Hat

historicimage

$27.29

1912 Chicago The Summer Resort Dad Hat

historicimage

$27.29

Chicago Deep Dish Pizza Dad Hat

AmericanCulinaryCulture

$23.09

Chicago USA Linocut Style Baseball Cap

Thistle-TShop

$25.19

Delicious Chicago Pizza Dad Hat

harebrained

$25.19

Chicago Style Beer mosaic design products. Baseball Cap

ColorCatalysts

$25.19

1912 Chicago The Summer Resort Baseball Cap

historicimage

$27.29

Retro Chicago Dad Hat

FrictionMaxxing

$25.19

Chicago Style Dad Hat

Illannoyed

$24.45

1930 Chicago Has Everything Baseball Cap

historicimage

$27.29

1912 Chicago The Summer Resort Baseball Cap

historicimage

$27.29

Chicago USA Linocut Style Dad Hat

Thistle-TShop

$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 Baseball Cap

GhostDawgs

$28.34

Da Pope! Chicago Style Hot Dog Baseball Cap

BerlinerKatzen

$25.19

Chicago USA Linocut Style Baseball Cap

Thistle-TShop

$25.19

Chicago USA Linocut Style Baseball Cap

Thistle-TShop

$25.19

Chicago, United States of America | Anime style Baseball Cap

ComicsFactory

$25.19

Chicago Illinois Retro Dad Hat

Oniyasha

$29.39

Michigan Ave Chicago Vintage Style Baseball Cap

Decal Mania

$26.87

Chicago Skyline Vintage Retro City Illustration Baseball Cap

Andruzito

$25.19

Chicago Style Hot Dog Beating Up Ketchup Dad Hat

BerlinerKatzen

$25.19

Historian Sticker: Painstakingly trained in the Chicago Manual of Style Dad Hat

anthropocynical

$25.19

Chicago Skyline – Graffiti Style T-Shirt Design - USA Travel City Art Dad Hat

Earth Celebration Designs

$23.09

i got that dog in me - Chicago Style Baseball Cap

Boxout

$25.19

Chicago | Post-impressionist painting style Dad Hat

ComicsFactory

$25.19

The Union, Chicago style Dad Hat

Ashact

$25.19

Chicago 1833 Windy City Pride Baseball Cap

NoulDesign

$23.09

Urban Streetwear Chicago Trend Dad Hat

Zuuag

$24.66

Urban Streetwear Chicago Trend Baseball Cap

Zuuag

$24.66

Chicago House Music Turntable Hot Graffiti Style Dad Hat

idabry

$29.39

Chicago Illinois License Plate Style Baseball Cap

levsal

$22.04

Chilly Bear Chicago Dad Hat

littlebitmad

$23.09

Chicago style hotdog Dad Hat

TavellynArt

$31.49

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 Baseball Cap

LimeAnaconda

$25.19

Hotdog Heros Chicago Dog Dad Hat

1mooreroy

$23.09

Chicago Hot Dog No Ketchup L Train Badge Dad Hat

Lyfeinsights

$25.19

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

AdamShirts7

$24.98

Windy City Hot Dog Flag Chicago Style Wiener Dad Hat

snowry

$24.14

Hey Chicago What Do You Say Dad Hat

carolineduvivier

$25.19

Chicago Stocking Cap Dog with Flag Baseball Cap

dangerhuskie

$25.19

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

AdamShirts7

$24.98

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 Baseball Cap

Any Color Designs

$27.29

CHICAGO – Gothic Streetwear Typography Design Baseball Cap

OxiSkor

$25.19

North Side Chicago Dog Dad Hat

dangerhuskie

$23.09

1921 Chicago International Graphic Arts Expo Baseball Cap

historicimage

$27.29

Item preview, Chicago Travel Illustration designed and sold by aio.

Chicago Travel Illustration Dad Hat

aio

$29.39

Chicago | Minimalist City Name | Vintage Travel Aesthetic Baseball Cap

MyMomentShirt

$27.29

Chicago Illinois Retro Badge Design Dad Hat

SleeplessLady

$23.09

Chicago Style Hot Dog Funny Quote Dad Hat

Verycutethings

$25.19

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

TKOprintdesigns

$23.09

Become a member.Get 25% off your first order.Plus other neat perks and exclusive savings to help you find the very thing.

Worldwide Shipping
Available as standard or express delivery
Learn more- opens in new window or tab
Secure Payments
100% Secure Payment with 256-bit SSL encryption
Learn more- opens in new window or tab
Free Return
Exchange or money back guarantee for all orders
Learn more- opens in new window or tab
Local Support
24/7 Dedicated support
Learn more- opens in new window or tab

Chicago Style Caps

Worldwide Shipping

Secure Payments

Free Return

Local Support

Shop

About

Help

Social