Chicago City & Flag

Chicago city and flag designs for people who love this city: the four stars of the Chicago flag, the 312 area code, the Windy City and the skyline, on beanies, crewnecks, tees and canvas.

Start with the Chicago flag beanie, embroidered with the flag's four six-pointed stars. Find the 312 beanie, crewneck and baby bodysuit in 312 Chicago, and the Windy City Hoops crew and kids tees in Windy City. For your part of town, see the neighborhood crewnecks. Made to order in the USA with free U.S. shipping.
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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.