Chicago: Walking Pizza Tour River North & Gold Coast

4.97

(119 reviews)

What’s the experience like?

I dropped a slice of pepperoni right off my plate before we’d even left the first stop. It landed cheese-side down, of course. Our guide, Marcus, just grinned and handed me a fresh napkin — “You’re not the first,” he said. I liked that. We started near Navy Pier, but it wasn’t touristy at all once we ducked into the first pizzeria. The smell was all tomato and warm dough, and there was this old guy at the counter who nodded at us like he’d seen a thousand groups come through.

The Chicago walking pizza tour really is just that — you walk, you eat, you listen to someone who knows their stuff. Marcus explained how deep dish came out of these neighborhoods (he called it “a casserole with pride”), then we crossed into River North where things got busier. You could hear the L train rattling above sometimes, and in one spot a delivery guy squeezed past us with flour dust on his shoes. That’s when we tried the Neapolitan slice — lighter crust, burnt bubbles on the edge. I didn’t expect to like it more than the thick stuff but… yeah, I did.

We wandered over to the Magnificent Mile next (I always thought it was just shopping), stopping for Roman-style pizza with this chewy base — almost focaccia-like. Marcus told us about Italian immigrants bringing their own recipes over, and how every place here does something a little different. At one point someone asked if Chicagoans ever agree on their favorite style; he just laughed and said “Not in my lifetime.”

After lunch we passed Holy Name Cathedral — bells ringing faintly in the background — and I realized how much of the city you actually see on this kind of day trip from Navy Pier through downtown Chicago. My jeans smelled like oregano for hours after. I still think about that Neapolitan slice sometimes when I’m hungry late at night.