Twenty years ago, this was just a dad and his son walking Chicago's neighborhoods on weekends — no business plan, no content calendar, just an honest habit of loving this city out loud. That habit eventually became Chicago Specials. The feeling never changed.
This hat is about as close as we can get to handing you that feeling instead of just describing it. Right now, every one sold is one of the only things keeping this a two-person, walk-it-yourself operation instead of another scraped directory — real neighborhoods, real research, no filler. Read the whole story on our About page →
I ❤ Chicago Trucker Hat — Black
$24.99The classic I ❤ Chicago on a high-profile foam front, built for the actual city, not the tourist-shop version of it.
Shop this on Printful →I ❤ Chicago Trucker Hat — Pink
$24.99Same build, same story, pink foam front — for anyone who'd rather their love letter to this city not be subtle.
Shop this on Printful →Checkout happens on Printful — they print, pack, and ship each hat, so nothing sits in our closet waiting to be mailed. Everything else about this project stays exactly as homemade as it's always been.