Free Shipping On Orders Over $99

TShirtPalace — Custom T-Shirts, Hoodies & Apparel

Search...

Search...

Home

Shop

Create Your Own

About Us

FAQs

Contact

/

Headwear

/

Beanies

/

Chicago Vintage Beanies

Chicago Vintage Beanies

Keep your head warm and your personality on full display. Our winter beanies feature the same hilarious, bold, and one-of-a-kind designs you love from T-Shirt Palace, just in hat form. Browse the funny hats below and find the perfect beanie to top off your look this season.

Safe Search: Off

Chicago Illinois Vintage Flag Beanie

Chicago Illinois Vintage Flag Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Flag Beanie

Chicago Flag Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Vintage Skyline Retro Illinois Pride Gift Beanie

Chicago Vintage Skyline Retro Illinois Pride Gift Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Southside Chicago Vintage Sign Distressed White Print Beanie

Southside Chicago Vintage Sign Distressed White Print Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Wrigleyville Illinois Chicago IL Vintage Beanie

Wrigleyville Illinois Chicago IL Vintage Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Wrigleyville Illinois Chicago Vintage Athletic Beanie

Wrigleyville Illinois Chicago Vintage Athletic Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Flag Vintage Beanie

Chicago Flag Vintage Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Bear Vintage Beanie

Chicago Bear Vintage Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Southside Chicago Il Vintage Distressed Beanie

Southside Chicago Il Vintage Distressed Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Vintage Emblem Beanie

Chicago Vintage Emblem Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Flag 312 Beanie

Chicago Flag 312 Beanie

Knit Cap Winter Beanie

$19.99

$24.99

I Still Call It Comiskey Chicago Baseball Vintage Beanie

I Still Call It Comiskey Chicago Baseball Vintage Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Shota Imanaga Chicago Baseball Vintage Cursive Beanie

Shota Imanaga Chicago Baseball Vintage Cursive Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago City Flag Distressed Bear Gift Beanie

Chicago City Flag Distressed Bear Gift Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Vintage Chicago Flag Beanie

Vintage Chicago Flag Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago House Music Vintage Chicago Flag Beanie

Chicago House Music Vintage Chicago Flag Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Vintage 80s Retro Style Funny Gift Beanie

Chicago Vintage 80s Retro Style Funny Gift Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago City Flag Vintage Beanie

Chicago City Flag Vintage Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Retro Gift Beanie

Chicago Retro Gift Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Flag Skyline Vintage Illinois City Retro Souvenir Beanie

Chicago Flag Skyline Vintage Illinois City Retro Souvenir Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Vintage Chicago Baseball Emblem Beanie

Vintage Chicago Baseball Emblem Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Teachers Union Vintage Apple Flag Red For Ed Beanie

Chicago Teachers Union Vintage Apple Flag Red For Ed Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Irish Chicago Flag Shamrock St Patrick's Day Beanie

Irish Chicago Flag Shamrock St Patrick's Day Beanie

Knit Cap Winter Beanie

$19.99

$24.99

From America Chicago Da Pope Leo XIV Funny Vintage Beanie

From America Chicago Da Pope Leo XIV Funny Vintage Beanie

Knit Cap Winter Beanie

$19.99

$24.99

I STILL CALL IT COMISKEY Chicago Baseball Vintage TShirt Beanie

I STILL CALL IT COMISKEY Chicago Baseball Vintage TShirt Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Handshake Beanie

Chicago Handshake Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Chicago Illinois Stamp Logo Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Cahokia Illinois Vintage Logo Beanie

Knit Cap Winter Beanie

$19.99

$24.99

The Original Berf Of Chicagoland Beanie

The Original Berf Of Chicagoland Beanie

Knit Cap Winter Beanie

$19.99

$24.99

Vintage Chicago Flag Beanie

Vintage Chicago Flag Beanie

Knit Cap Winter Beanie

$19.99

$24.99

1

2

3

4

Sign Up For Our Newsletter

Receive 10% Off Your First Order & Discounts in your inbox every week!

[email protected]

Monday-Friday
10:00 AM - 5:00 PM EST

21440, Melrose Ave.
Southfield, MI 48075

TSHIRT PALACE

TShirtPalace is an online shop specializing in funny, pop-culture, and custom graphic apparel for men, women, and kids, with thousands of unique designs and custom and personalized products

Follow Us

Company

Policies

Follow Us

Accreditations

Customer Reviews

Copyright ©2010-2026 TShirtPalace.

Payment Methods