Vintage Chicago Beanies

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Knit Cap Winter Beanie

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Vintage Chicago Flag Kati Licensed 12" Camo Cuffed Beanie

$32.99

$38.99

Kati Licensed 12" Camo Cuffed Beanie

Vintage Chicago Flag

Vintage Chicago Illinois Skyline Bears Football Short Acrylic Beanie

$21.99

$27.99

Short Acrylic Beanie

Vintage Chicago Illinois Skyline Bears Football

+20 more

Vintage Chicago Flag Short Acrylic Beanie

$21.99

$27.99

Short Acrylic Beanie

Vintage Chicago Flag

+2 more

Chicago City Skyline Flag Vintage The Baniff Cuffed Pom Beanie

$38.99

$49.99

The Baniff Cuffed Pom Beanie

Chicago City Skyline Flag Vintage

$38.99

$49.99

The Baniff Cuffed Pom Beanie

Vintage Chicago Flag

Nope Not Again Funny Trump Short Acrylic Beanie

$21.99

$27.99

Short Acrylic Beanie

Nope Not Again Funny Trump

+20 more

Irish Chicago Flag Shamrock St Patrick's Day Beanie

$19.99

$24.99

Knit Cap Winter Beanie

Irish Chicago Flag Shamrock St Patrick's Day

+20 more

Cool Retro Cubs Bear The Baniff Cuffed Pom Beanie

$38.99

$49.99

The Baniff Cuffed Pom Beanie

Cool Retro Cubs Bear

$19.99

$24.99

Knit Cap Winter Beanie

Chicago Flag

+20 more

Vintage Chicago Illinois Flag Tees Skyline Stripe Pom Pom Beanie

$21.99

$27.99

Stripe Pom Pom Beanie

Vintage Chicago Illinois Flag Tees Skyline

+1 more

Chicago House Music Vintage Chicago Flag Kati Licensed 12" Camo Cuffed Beanie

$32.99

$38.99

Kati Licensed 12" Camo Cuffed Beanie

Chicago House Music Vintage Chicago Flag

$32.99

$38.99

Kati Licensed 12" Camo Cuffed Beanie

Retro Cubs Baseball Sports Fan

$19.99

$24.99

Knit Cap Winter Beanie

Vintage Chicago Distressed

+16 more

$19.99

$24.99

Knit Cap Winter Beanie

Vintage Chicago Baseball Emblem

+20 more

$27.99

$32.99

Sustainable Knit Beanie

Chicago Vintage Classic Team Logo

Vintage Chicago Illinois Skyline Apparel Pom Pom 12in Knit Beanie

$24.99

$27.99

Pom Pom 12in Knit Beanie

Vintage Chicago Illinois Skyline Apparel

+20 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 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

Chicago Bear Vintage Kati Licensed 12" Camo Cuffed Beanie

$32.99

$38.99

Kati Licensed 12" Camo Cuffed Beanie

Chicago Bear Vintage

Chicago Vintage Emblem Sustainable Knit Beanie

$27.99

$32.99

Sustainable Knit Beanie

Chicago Vintage Emblem

Chicago Flag Vintage Stripe Pom Pom Beanie

$21.99

$27.99

Stripe Pom Pom Beanie

Chicago Flag Vintage

+1 more

70S 80S Usa City Vintage Chicago Pom Pom 12in Knit Beanie

$24.99

$27.99

Pom Pom 12in Knit Beanie

70S 80S Usa City Vintage Chicago

+12 more

Vintage Chicago Illinois Est. 1833 Souvenir Short Acrylic Beanie

$21.99

$27.99

Short Acrylic Beanie

Vintage Chicago Illinois Est. 1833 Souvenir

+12 more

Vintage Chicago Illinois Est. 1833 Gift The Baniff Cuffed Pom Beanie

$38.99

$49.99

The Baniff Cuffed Pom Beanie

Vintage Chicago Illinois Est. 1833 Gift

Cool Bear With Beanie Sunglasses Vintage Chicago Short Acrylic Beanie

$21.99

$27.99

Short Acrylic Beanie

Cool Bear With Beanie Sunglasses Vintage Chicago

+20 more

Us American City 70S Retro Usa Vintage Chicago The Baniff Cuffed Pom Beanie

$38.99

$49.99

The Baniff Cuffed Pom Beanie

Us American City 70S Retro Usa Vintage Chicago

Da Pope Pope Leo XIV Provost From America Chicago Stripe Pom Pom Beanie

$21.99

$27.99

Stripe Pom Pom Beanie

Da Pope Pope Leo XIV Provost From America Chicago

+1 more

Chicago He Had It Coming! 1920s Jazz Musical Theatre Pom Pom 12in Knit Beanie

$24.99

$27.99

Pom Pom 12in Knit Beanie

Chicago He Had It Coming! 1920s Jazz Musical Theatre

+12 more

$19.99

$24.99

Knit Cap Winter Beanie

Chicago Retro Flag Vintage

+16 more

Southside Chicago Vintage Sign Distressed White Print Short Acrylic Beanie

$21.99

$27.99

Short Acrylic Beanie

Southside Chicago Vintage Sign Distressed White Print

+12 more

Wrigleyville Illinois Chicago Vintage Athletic Stripe Pom Pom Beanie

$21.99

$27.99

Stripe Pom Pom Beanie

Wrigleyville Illinois Chicago Vintage Athletic

Chicago Vintage Skyline Retro Illinois Pride Gift Pom Pom 12in Knit Beanie

$24.99

$27.99

Pom Pom 12in Knit Beanie

Chicago Vintage Skyline Retro Illinois Pride Gift

+12 more

I STILL CALL IT COMISKEY Chicago Baseball Vintage TShirt Kati Licensed 12" Camo Cuffed Beanie

$32.99

$38.99

Kati Licensed 12" Camo Cuffed Beanie

I STILL CALL IT COMISKEY Chicago Baseball Vintage TShirt

Chicago Vintage 80s Retro Style Funny Gift Stripe Pom Pom Beanie

$21.99

$27.99

Stripe Pom Pom Beanie

Chicago Vintage 80s Retro Style Funny Gift

+1 more

Chicago Illinois Vintage Flag The Baniff Cuffed Pom Beanie

$38.99

$49.99

The Baniff Cuffed Pom Beanie

Chicago Illinois Vintage Flag

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About this collection

Shop vintage chicago beanies with a wide range of designs available. Browse 96+ options and filter by different styles like hoodies, mugs, and hats, or sort by popularity, newest, or trending. All items are printed on demand using advanced printing technology and usually ship within 1–2 business days.

Shop Vintage Chicago Beanies

Shop vintage chicago beanies made for customers looking for unique designs, thoughtful gifts, and everyday apparel. This collection brings together designs that fit different occasions, interests, and personal styles.

Browse options in different colors, sizes, and fits to find the right look. Use filters and sorting tools to view related styles, newest arrivals, trending designs, and popular picks.

Each item is printed on demand with state-of-the-art equipment to help deliver sharp, long-lasting results. Most orders typically ship within 1–2 business days after being placed.