Sale’s in Session: Up to 40% off Back to School
ends soon
Sell your art
Login
Signup
Caps
Retro mountain with trees
Redbubble logo
Explore
For You
Retro Gaming
Horror
Sci-Fi
80s Fandoms
Pop-Culture
Fresh Finds
Fan Art
Blockbuster Movies
Clothing
New
All Clothing
T-Shirts
New
Hoodies & Sweatshirts
Hats
Socks
Dresses
Tank Tops
Stickers
All Stickers
Holographic Stickers
Funny Stickers
Car Stickers
Bumper Stickers
Water Bottle Stickers
Cool Stickers
Anime Stickers
Laptop Stickers
Magnets
Custom Stickers
Phone Cases
All Phone Cases
iPhone Cases
Samsung Galaxy
New
Wall Art
All Wall Art
Posters
Photographic Prints
Art Prints
Tapestries
Canvas Prints
Framed Prints
Art Board Prints
Home & Living
All Home & Living
Mugs
Throw Pillows
Throw Blankets
Tapestries
Magnets
Aprons
Coasters
Jigsaw Puzzles
Duvet Covers
Acrylic Blocks
Clocks
Shower Curtains
Bath Mats
Kids & Babies
All Kids Clothes
Kids T-Shirts
Baby One-Pieces
Kids Pullover Hoodies
Accessories
All Accessories
Hats
Socks
Pins
Backpacks
Tech Accessories
Tote Bags
Makeup Bags
Toiletry Bags
Zipper Pouches
Duffle Bags
Scarves
Stationery & Office
All Stationery & Office
Greeting Cards
Spiral Notebooks
Mouse Pads & Desk Mats
Postcards
Hardcover Journals
Gifts
All Gifts
Gifts for Book Lovers
Gifts for Gamers
Gifts for Her
Gifts for Him
Gifts for Animal Lovers
Gifts Under $50
Gifts for Outdoorsy Types
Gifts for Kids
Stocking Stuffers
Gift Cards
Chicago Style Caps
882 items
Hats
Filters (2)
882 items
Most Relevant
Chicago Style Giardiniera Dad Hat
jnedza
$24.98
$29.39
(15% off)
Scottie Pippen Basketball Legend Chicago Signature Vintage Retro 80s 90s Bootleg Rap Style Dad Hat
Isabella Heller ⭐⭐⭐⭐⭐(316)
$23.19
$27.29
(15% off)
Chicago logo circle Baseball Cap
Backstage by Leyzel
$20.15
$25.19
(20% off)
Baseball cubs Dad Hat
sabinako
$19.62
$23.09
(15% off)
Chicago Style Dad Hat
Shannon Alexis Designs
$31.22
$36.73
(15% off)
HOUSE MUSIC - Font Style (black) Baseball Cap
Discothreadz
$20.15
$25.19
(20% off)
Love Chicago Style Baseball Cap
StylesOfLove
$21.83
$27.29
(20% off)
Chicago Style Hot Dog Dad Hat
bouquetofstars
$21.41
$25.19
(15% off)
Chicago Pizza Wave Dad Hat
wojysmokes
$21.41
$25.19
(15% off)
Jewels Baseball Cap
Illannoyed
$19.48
$24.35
(20% off)
Vintage Style Chicago License Plate Baseball Cap
Decal Mania
$21.49
$26.87
(20% off)
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
$23.19
$27.29
(15% off)
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
$23.19
$27.29
(15% off)
Sometimes I feel like I'm melting Baseball Cap
wojysmokes
$20.15
$25.19
(20% off)
Chicago Bean Vintage Style Decal Baseball Cap
Decal Mania
$21.49
$26.87
(20% off)
American Style,Illinois. Dad Hat
JoyfulCreations
$21.41
$25.19
(15% off)
Chicago Icons: Popcorn Dad Hat
buhloop
$19.62
$23.09
(15% off)
Chicago Style Hot Dog Baseball Cap
dudelinart
$20.15
$25.19
(20% off)
Chicago Style Hotdog Baseball Cap
MalignWineArt
$20.15
$25.19
(20% off)
Chicago Postcard Style Image Dad Hat
purplerosemary
$30.33
$35.68
(15% off)
Deep Dish, Deep Loyalty Baseball Cap
chicagocap
$18.47
$23.09
(20% off)
Chicago Style Pizza Pattern - Pizza - Stadium - Field - license - flag - sears tower - cloud gate Baseball Cap
Dude Stuff
$23.51
$29.39
(20% off)
Chicago Style Hot Dog Urban Foodie Emblem Dad Hat
snowry
$20.52
$24.14
(15% off)
Wrigley Field Mug Pattern - Available on socks and more Baseball Cap
Dude Stuff
$23.51
$29.39
(20% off)
Soldier Field ( Chicago Bears ) - Available on socks and more Dad Hat
Dude Stuff
$24.98
$29.39
(15% off)
Illinois DMV License Plate and State Flag Pattern Dad Hat
Dude Stuff
$24.98
$29.39
(15% off)
Soldier Field Pattern Baseball Cap
Dude Stuff
$23.51
$29.39
(20% off)
Chicago Style Hot Dog Dad Hat
carolineduvivier
$21.41
$25.19
(15% off)
Chicago Skyline Pulse Dad Hat
Dude Stuff
$24.98
$29.39
(15% off)
Chicago Mondrian style poster Baseball Cap
CMYKStudio
$20.15
$25.19
(20% off)
Chicago Skyline, Wes Anderson Style Baseball Cap
Skyline-Design5
$20.15
$25.19
(20% off)
Taste of America, Chicago Style Hotdog Dad Hat
MalignWineArt
$21.41
$25.19
(15% off)
The Bandits, Chicago style Dad Hat
Ashact
$21.41
$25.19
(15% off)
Pittsburgh Chi Style Baseball Cap
jrmclaughlin
$18.47
$23.09
(20% off)
Chicago Style HotDog Baseball Cap
Nanagans
$20.15
$25.19
(20% off)
Buzz’n Bear Dad Hat
Illannoyed
$20.69
$24.35
(15% off)
Chicago Style – Funny Hot Dog Lover Baseball Cap
dudelinart
$20.15
$25.19
(20% off)
Chicago Hot Dog - Chicago Dog Style Dad Hat
luckymooninc
$23.19
$27.29
(15% off)
Chicago Cloud Gate Windy City Landmark Design Baseball Cap
castillomiami
$20.99
$26.24
(20% off)
Chicago Mondrian style poster 3D Dad Hat
CMYKStudio
$21.41
$25.19
(15% off)
1913 Chicago The Summer Resort Baseball Cap
historicimage
$21.83
$27.29
(20% off)
1912 Chicago The Summer Resort Baseball Cap
historicimage
$21.83
$27.29
(20% off)
Chicago USA Linocut Style Dad Hat
Thistle-TShop
$21.41
$25.19
(15% off)
1912 Chicago The Summer Resort Baseball Cap
historicimage
$21.83
$27.29
(20% off)
1930 Chicago Has Everything Baseball Cap
historicimage
$21.83
$27.29
(20% off)
Retro Chicago Baseball Cap
FrictionMaxxing
$20.15
$25.19
(20% off)
Chicago Deep Dish Pizza Baseball Cap
AmericanCulinaryCulture
$18.47
$23.09
(20% off)
1912 Chicago The Summer Resort Dad Hat
historicimage
$23.19
$27.29
(15% off)
Delicious Chicago Pizza Dad Hat
harebrained
$21.41
$25.19
(15% off)
Chicago, United States of America | Anime style Baseball Cap
ComicsFactory
$20.15
$25.19
(20% off)
Chicago Style Dad Hat
Illannoyed
$20.69
$24.35
(15% off)
Da Pope! Chicago Style Hot Dog Dad Hat
BerlinerKatzen
$21.41
$25.19
(15% off)
Chicago USA Linocut Style Baseball Cap
Thistle-TShop
$20.15
$25.19
(20% off)
Chicago USA Linocut Style Dad Hat
Thistle-TShop
$21.41
$25.19
(15% off)
Chicago USA Linocut Style Dad Hat
Thistle-TShop
$21.41
$25.19
(15% off)
Chicago Deep Dish Pizza Lover Graphic Dad Hat
BoringClothes
$20.52
$24.14
(15% off)
Chicago Illinois Retro Dad Hat
Oniyasha
$24.98
$29.39
(15% off)
Chicago swiss style poster Dad Hat
CMYKStudio
$21.41
$25.19
(15% off)
Chicago Basketball - Vintage Skyline Baseball Cap
RonnyMilleo
$18.47
$23.09
(20% off)
Michigan Ave Chicago Vintage Style Dad Hat
Decal Mania
$22.84
$26.88
(15% off)
Chicago Style Hot Dog Beating Up Ketchup Dad Hat
BerlinerKatzen
$21.41
$25.19
(15% off)
Historian Sticker: Painstakingly trained in the Chicago Manual of Style Baseball Cap
anthropocynical
$20.15
$25.19
(20% off)
Chicago Skyline – Graffiti Style T-Shirt Design - USA Travel City Art Dad Hat
Earth Celebration Designs
$19.62
$23.09
(15% off)
i got that dog in me - Chicago Style Dad Hat
Boxout
$21.41
$25.19
(15% off)
The Union, Chicago style Baseball Cap
Ashact
$20.15
$25.19
(20% off)
Urban Streetwear Chicago Trend Baseball Cap
Zuuag
$19.73
$24.66
(20% off)
Chicago | Post-impressionist painting style Baseball Cap
ComicsFactory
$20.15
$25.19
(20% off)
Chicago 1833 Windy City Pride Dad Hat
NoulDesign
$19.62
$23.09
(15% off)
Urban Streetwear Chicago Trend Baseball Cap
Zuuag
$19.73
$24.66
(20% off)
Chicago House Music Turntable Hot Graffiti Style Dad Hat
idabry
$24.98
$29.39
(15% off)
Chicago style hotdog Dad Hat
TavellynArt
$21.41
$25.19
(15% off)
Chicago 2026 Layered Typography Windy City Design Dad Hat
cabana.space
$21.41
$25.19
(15% off)
Chicago Basketball Retro Style – Windy City Vintage Design Baseball Cap
Ancestral-Shop
$18.47
$23.09
(20% off)
Chicago Hot Dog No Ketchup L Train Badge Dad Hat
Lyfeinsights
$21.41
$25.19
(15% off)
Chicago Food Department Dad Hat
Illannoyed
$20.69
$24.35
(15% off)
Iconic Chicago Architecture Meets Deep Dish Baseball Cap
BoringClothes
$19.31
$24.14
(20% off)
Chicago Illinois License Plate Style Baseball Cap
levsal
$17.63
$22.04
(20% off)
Chicago Beef Department Baseball Cap
Illannoyed
$19.48
$24.35
(20% off)
Eagle Man Baseball Cap
Illannoyed
$19.48
$24.35
(20% off)
Chilly Bear Chicago Baseball Cap
littlebitmad
$18.47
$23.09
(20% off)
Hotdog Heros Chicago Dog Dad Hat
1mooreroy
$19.62
$23.09
(15% off)
Chicago Style Baseball Cap
LimeAnaconda
$20.15
$25.19
(20% off)
Chicago Logo: Collegiate design with a sporty urban style Baseball Cap
AdamShirts7
$19.98
$24.98
(20% off)
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
$21.83
$27.29
(20% off)
CHICAGO – Gothic Streetwear Typography Design Baseball Cap
OxiSkor
$20.15
$25.19
(20% off)
Chicago Logo: Collegiate design with a sporty urban style Dad Hat
AdamShirts7
$21.23
$24.98
(15% off)
Chicago Stocking Cap Dog with Flag Dad Hat
dangerhuskie
$21.41
$25.19
(15% off)
Hey Chicago What Do You Say Dad Hat
carolineduvivier
$21.41
$25.19
(15% off)
Chicago | Minimalist City Name | Vintage Travel Aesthetic Dad Hat
MyMomentShirt
$23.19
$27.29
(15% off)
North Side Chicago Dog Baseball Cap
dangerhuskie
$18.47
$23.09
(20% off)
Become a member.
Get 25% off your first order.
Plus other neat perks and exclusive savings to help you find the very thing.
Sign up
Previous
1
2
3
10
Next
Chicago
Hot Dog
Illinois
Food
Windy City
New York
Detroit
Dallas
Denver
Houston
Nyc
Philadelphia
St Louis
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
