Chicago Sweatshirts

Every Chicago sweatshirt we make, in one place. Start with the embroidered Chicago sweatshirts: the Est. 1837 crewneck and the neighborhood crewnecks, stitched in satin thread rather than printed. For Sundays there are the printed game-day crews: the Chicago Football Est. 1920 and Skyline Football 312 crewnecks, the Est. 1966 and retro 90s basketball crews, Windy City Hoops and the Green Bay Sucks crews, all in game day sweatshirts.

Want a Chicago hoodie? The Caleb Williams Jump Man hoodie and the Bears retro arched hoodie are independent fan designs; see Chicago hoodies. Every Chicago crewneck is a classic unisex fit, so size up one for an oversized look. Made to order in the USA with free U.S. shipping.
Skip to results list
97 items

Filter

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

Embroidered city crewneck on ivory

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.
How does sizing run?

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”.
When will my order ship?

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.
What if something arrives damaged?

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