Windy City Sweatshirts & Kids Tees

Chicago has answered to the Windy City since the 1800s, and the lake wind in January makes the name easy to believe. These Windy City designs put the nickname front and center.

Shop the Windy City Hoops skyline crewneck and the matching youth crew, the Chicago Skyline Football 312 crew, and the Windy City Kid toddler tee and Windy City Little Hooper youth tee for the smallest fans. Made to order in the USA, free U.S. shipping. See also Chicago basketball and youth and baby.

More to explore

New arrivals

New vintage bull canvas in a brick loft office

New Arrivals

Best-selling canvas hanging in a living room

Best Sellers

Dark bull canvas hanging in a moody home bar

Chicago Wall Art

Chicago Embroidered Crews

Little Rookie baby bodysuit in natural cream

Youth & Baby

Good to know

The three questions we are asked most. The full list is on the FAQ page.

Crewnecks and hoodies are unisex and run roomy, so size down for a fitted look. Every apparel page has a size chart under “Size guide”.

Everything is printed to order. Most pieces leave our print partners in 3–7 business days, and most U.S. orders arrive within 7–12 business days with tracking.

Message us through the contact form within 30 days with your order number and a photo, and we will send a free replacement.