Headwears

Chicago Headwears

Headwears Chicago Gifts

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+7 styles

+20 more

Delicious Chicago Pizza Beanie

Knit Cap Winter Beanie

$19.99

$24.99

+1 styles

Chicago Flag Santa Hat

Premium Christmas Santa Hat

$19.99

$24.99

Chicago Illinois Vintage Flag Bucket Hat

+1 styles

+1 more

Chicago Illinois Vintage Flag Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

+7 styles

+20 more

City Of Chicago Beanie

Knit Cap Winter Beanie

$19.99

$24.99

+1 styles

+1 more

Chicago Retro Gift Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

+7 styles

+15 more

Chicago Hat

Trucker Hat

$19.99

$24.99

+1 styles

+1 more

Kyle From Chicago Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Chicago Football Legend Chicago Skyline Bucket Hat

+1 styles

+1 more

Chicago Football Legend Chicago Skyline Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Chicago for Chicago Flag Artwork with Skulls Hat

+7 styles

+15 more

Chicago for Chicago Flag Artwork with Skulls Hat

Trucker Hat

$19.99

$24.99

Chicago City Skyline Lights At Night Chicago Illinois USA Visor

+1 styles

+2 more

Chicago City Skyline Lights At Night Chicago Illinois USA Visor

Valucap Bio-Washed Visor

$23.99

$29.99

Chicago Rat Hole Hilarious Souvenir From Chicago Funny Beanie

+7 styles

+20 more

Chicago Rat Hole Hilarious Souvenir From Chicago Funny Beanie

Knit Cap Winter Beanie

$19.99

$24.99

+7 styles

+15 more

Chicago Illinois Hat

Trucker Hat

$19.99

$24.99

+1 styles

Chicago Roots Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

+7 styles

+16 more

Vintage Chicago Distressed Beanie

Knit Cap Winter Beanie

$19.99

$24.99

+7 styles

+20 more

Chicago Style Hot Dog Summer Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Illinois Skyline Travel To Chicago Love Beanie

+7 styles

+16 more

Chicago Illinois Skyline Travel To Chicago Love Beanie

Knit Cap Winter Beanie

$19.99

$24.99

+7 styles

+16 more

Southside Chicago Throwback Beanie

Knit Cap Winter Beanie

$19.99

$24.99

+1 styles

Chicago funny Illinois Chicago Gift Chicago Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

+7 styles

+15 more

Chicago Throwback Design Classic Hat

Trucker Hat

$19.99

$24.99

+7 styles

+15 more

Chicago Skyline Illinois Vintage Hat

Trucker Hat

$19.99

$24.99

Chicago Flag Skyline Vintage Illinois City Retro Souvenir Visor

+1 styles

+2 more

Chicago Flag Skyline Vintage Illinois City Retro Souvenir Visor

Valucap Bio-Washed Visor

$23.99

$29.99

+1 styles

Chicago - Chicago Flag Sweatshirt Sweatshirt Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Chicago City Flag Downtown Skyline Chicago Skyline Visor

+1 styles

+2 more

Chicago City Flag Downtown Skyline Chicago Skyline Visor

Valucap Bio-Washed Visor

$23.99

$29.99

+1 styles

+8 more

Chicago Illinois Visor

Valucap Bio-Washed Visor

$23.99

$29.99

+1 styles

Cool Bear With Beanie Sunglasses Vintage Chicago Santa Hat

Premium Christmas Santa Hat

$19.99

$24.99

Chicago Flaggift Southside Chicagogift City Of Chicago Flag Meaningful Gift Beanie

+7 styles

+16 more

Chicago Flaggift Southside Chicagogift City Of Chicago Flag Meaningful Gift Beanie

Knit Cap Winter Beanie

$19.99

$24.99

+1 styles

Wrigleyville Chicago Baseball American Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Wrigleyville Chicago Baseball American Beanie

+7 styles

+16 more

Wrigleyville Chicago Baseball American Beanie

Knit Cap Winter Beanie

$19.99

$24.99

+1 styles

Wrigleyville Chicago Baseball American Santa Hat

Premium Christmas Santa Hat

$19.99

$24.99

+1 styles

Chicago City Skyline Flag Vintage Chicago City Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99