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Windy City Beanies

Results updated

Custom Knit Cap Winter Beanie
Custom

From $19.99

Knit Cap Winter Beanie

Add your own photo, logo or text

Customize →

Chicago Flag Kati Licensed 12" Camo Cuffed Beanie

$32.99

$38.99

Kati Licensed 12" Camo Cuffed Beanie

Chicago Flag

Illinois Stripe Pom Pom Beanie

$21.99

$27.99

Stripe Pom Pom Beanie

Illinois

Everything Dope About America Comes From Chicago Quote Sustainable Knit Beanie

$27.99

$32.99

Sustainable Knit Beanie

Everything Dope About America Comes From Chicago Quote

Vintage Chicago Flag Short Acrylic Beanie

$21.99

$27.99

Short Acrylic Beanie

Vintage Chicago Flag

+2 more
Chicago Flag Beanie

$19.99

$24.99

Knit Cap Winter Beanie

Chicago Flag

+20 more
City Of Chicago Illinois Flag Windy City Beanie

$19.99

$24.99

Knit Cap Winter Beanie

City Of Chicago Illinois Flag Windy City

+16 more
Vintage Chicago The Windy City Illinois EST 1848 Beanie

$19.99

$24.99

Knit Cap Winter Beanie

Vintage Chicago The Windy City Illinois EST 1848

+20 more
Chicago Pride Windy City Classic Beer Label Short Acrylic Beanie

$21.99

$27.99

Short Acrylic Beanie

Chicago Pride Windy City Classic Beer Label

+12 more
Chicago Flag 312 Pom Pom 12in Knit Beanie

$24.99

$27.99

Pom Pom 12in Knit Beanie

Chicago Flag 312

+20 more
Chicago Retro Gift The Baniff Cuffed Pom Beanie

$38.99

$49.99

The Baniff Cuffed Pom Beanie

Chicago Retro Gift

Chi Chicago City Skyline Of Downtown Chicago Illinois Pom Pom 12in Knit Beanie

$24.99

$27.99

Pom Pom 12in Knit Beanie

Chi Chicago City Skyline Of Downtown Chicago Illinois

+2 more
Distressed Chicago Flag Polish Poland Eagle Sustainable Knit Beanie

$27.99

$32.99

Sustainable Knit Beanie

Distressed Chicago Flag Polish Poland Eagle

Chicago City Skyline Flag Vintage Chicago City Pom Pom 12in Knit Beanie

$24.99

$27.99

Pom Pom 12in Knit Beanie

Chicago City Skyline Flag Vintage Chicago City

+12 more
Cahokia Illinois Vintage Logo Sustainable Knit Beanie

$27.99

$32.99

Sustainable Knit Beanie

Cahokia Illinois Vintage Logo

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About this collection

Browse windy city beanies designed for everyday wear, gifts, and special occasions. Choose from 55+ options and use filters to explore other styles like hoodies, hats, mugs and more, or sort by newest, trending, and most popular. Each item is printed on demand using state-of-the-art equipment for high-quality results and typically ships within 1–2 business days.

Windy City Beanies Collection

Discover windy city beanies designed for everyday wear, awareness events, and meaningful gifts. Whether you're shopping for yourself or looking for something special, this collection offers designs that highlight personal style and purpose.

Choose from a wide range of styles including bold graphics, minimalist designs, and classic looks. Our beanies are available in multiple sizes, colors, and fits to match your preferences and ensure all-day comfort.

Looking for more options? Explore this design across other styles like hoodies, hats, mugs and more to find the perfect match. Every item is printed on demand using advanced printing technology for high-quality results and typically ships within 1–2 business days.

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