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+7 styles

+20 more

Chicago Flag Beanie

Knit Cap Winter Beanie

$19.99

$24.99

+7 styles

+20 more

Chicago Illinois Vintage Flag Beanie

Knit Cap Winter Beanie

$19.99

$24.99

+1 styles

+1 more

Chicago Flag Vintage Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

+7 styles

+20 more

Chicago Flag Skyline Beanie

Knit Cap Winter Beanie

$19.99

$24.99

+1 styles

+1 more

Chicago Flag 312 Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

+1 styles

+1 more

Chicago Flag Star Logo Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

+1 styles

Vintage Chicago Flag Santa Hat

Premium Christmas Santa Hat

$19.99

$24.99

+1 styles

+1 more

Chicago Flag Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Chicago House Music Vintage Chicago Flag Bucket Hat

+1 styles

+1 more

Chicago House Music Vintage Chicago Flag Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

+1 styles

Fly The W Chicago Flag Santa Hat

Premium Christmas Santa Hat

$19.99

$24.99

+1 styles

+8 more

Chicago City Flag Vintage Visor

Valucap Bio-Washed Visor

$23.99

$29.99

+1 styles

+1 more

Vintage Chicago Flag Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

+7 styles

+20 more

Chicago W Flag Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Irish Chicago Flag Shamrock St Patrick's Day Bucket Hat

+1 styles

+1 more

Irish Chicago Flag Shamrock St Patrick's Day Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Chicago City Flag Distressed Bear Gift Bucket Hat

+1 styles

+1 more

Chicago City Flag Distressed Bear Gift Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

+7 styles

+46 more

Chicago City Flag W Hat

Trucker Hat

$19.99

$24.99

Chicago - Chicago Flag Sweatshirt Sweatshirt Beanie

+7 styles

+16 more

Chicago - Chicago Flag Sweatshirt Sweatshirt Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago for Chicago Flag Artwork with Skulls Visor

+1 styles

+2 more

Chicago for Chicago Flag Artwork with Skulls Visor

Valucap Bio-Washed Visor

$23.99

$29.99

+1 styles

+1 more

Deep Dish Chicago Pizza Flag Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Distressed Chicago Flag Polish Poland Eagle Hat

+7 styles

+46 more

Distressed Chicago Flag Polish Poland Eagle Hat

Trucker Hat

$19.99

$24.99

+7 styles

+25 more

Vintage Chicago Flag Hat

Trucker Hat

$19.99

$24.99

Chicago Flaggift Southside Chicagogift City Of Chicago Flag Meaningful Gift Visor

+1 styles

+2 more

Chicago Flaggift Southside Chicagogift City Of Chicago Flag Meaningful Gift Visor

Valucap Bio-Washed Visor

$23.99

$29.99

City Of Chicago Illinois Flag Windy City Beanie

+7 styles

+16 more

City Of Chicago Illinois Flag Windy City Beanie

Knit Cap Winter Beanie

$19.99

$24.99

+1 styles

Chicago Skyline Race Car Chicago Flag Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Chicago Flag Skyline Vintage Illinois Usa Souvenir Visor

+1 styles

+2 more

Chicago Flag Skyline Vintage Illinois Usa Souvenir Visor

Valucap Bio-Washed Visor

$23.99

$29.99

+1 styles

Chicago Flag Skyline Pride Illinois Vintage Bucket Hat

Legacy Cool Fit Booney Bucket Hat

$54.99

$64.99

Cool Chicago Flag Polish Eagle Funny Illinois Emblem Visor

+1 styles

+2 more

Cool Chicago Flag Polish Eagle Funny Illinois Emblem Visor

Valucap Bio-Washed Visor

$23.99

$29.99

+1 styles

Chicago Gift Chicago Flag Gift Santa Hat

Premium Christmas Santa Hat

$19.99

$24.99

Chicago Flag Skyline Vintage Illinois City Retro Souvenir Hat

+7 styles

+15 more

Chicago Flag Skyline Vintage Illinois City Retro Souvenir 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