Wear the Love Letter

Real Chicago merch that funds the actual thing — right now, it's the only way to back this directly.

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 Heart Chicago trucker hat in black, foam front with mesh back

I ❤ Chicago Trucker Hat — Black

$24.99

The classic I ❤ Chicago on a high-profile foam front, built for the actual city, not the tourist-shop version of it.

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I Heart Chicago trucker hat in pink, foam front with mesh back

I ❤ Chicago Trucker Hat — Pink

$24.99

Same build, same story, pink foam front — for anyone who'd rather their love letter to this city not be subtle.

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This hat is one of the only ways to support Chicago Specials directly right now. Buying one keeps a father-and-son project walking this city block by block and writing it down honestly, instead of scraping listings from somewhere else.

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.

An editorial collage of Chicago foods from The Bear: Italian beef, deep dish, a hot dog, and a growling purple bear
📰 The Scoop

The Bear Ate Chicago

Every restaurant, dive, diner, bakery, and beef stand that made its way onto the show — plus an interactive map of every stop.

Read the Story →