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Chicago: Food Walking Tour with Deep Dish Pizza & Hot Dog

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Free cancellationTravelers' pick

1/26

Duration3h

GroupUp to 16

LanguagesEN

Mobile ticketAccepted

Walk Chicago’s heart for deep-dish pizza hot dogs & city legends

You’ll walk through downtown Chicago tasting deep-dish pizza, classic hot dogs “dragged through the garden,” Italian beef sandwiches, and even sample the original brownie at Palmer House Hilton. Your local guide shares stories behind each bite as you pass icons like Millennium Park and Cloud Gate—plus you’ll get a bonus bike or kayak rental to keep exploring if you want.

Step-by-step itinerary

Meet guide and introduction
Eat stuffed Chicago pizza pie
Walk Michigan Avenue and Route 66
Taste Chicago-style hot dog
See Wrigley Building skyscraper
Walk Chicago Pedway or Loop
Pass through The Loop district
Visit Chicago Theatre marquee (AM tours only)
Tour Millennium Park (AM tours only)
See Cloud Gate "The Bean" (AM tours only)
View Crown Fountain (AM tours only)
See Pritzker Pavilion (AM tours only)
Enjoy original recipe brownie (AM tours only)
Visit Holy Name Cathedral (PM tours only)
See Historic Water Tower (PM tours only)
Receive free 2-hour bike or kayak rental

The Experience

The first thing I noticed was the smell—cheese and tomato sauce drifting out onto the sidewalk as we met our guide outside the pizza place. It was just after 11, a bit cloudy but not cold, and people were already lining up for their lunch break. Our guide (I think her name was Jamie?) handed us slices of deep-dish that were so heavy you had to use both hands. She told us how this pizza isn’t something you just grab on your way home—it’s more like a meal you plan your day around. I tried not to burn my tongue but failed, which made Jamie laugh. Honestly, worth it.

We wandered down Michigan Avenue after that, passing people in suits and kids chasing pigeons near Millennium Park. The city felt busy but not rushed—maybe because we kept stopping for bites and stories. At Max’s Take Out, Jamie showed us how to “drag it through the garden”—that’s what they say when you get a Chicago-style hot dog with all the toppings. I tried saying it myself and totally messed up; the guy behind the counter grinned anyway and piled on the pickles and peppers. The snap of that first bite is weirdly satisfying. I didn’t expect to care about a hot dog but here we are.

Somewhere between the Wrigley Building and Cloud Gate (the Bean really does look different from every angle), I realized I’d stopped thinking about my phone or what time it was. There was this moment at Palmer House Hilton where we tasted the original brownie recipe—still warm somehow—and Jamie explained how it was invented for the World’s Fair in 1893. The lobby smelled faintly of old wood polish and coffee. It felt like stepping sideways into another era for a second.

I’m not sure if it was the food or just being with people who actually live here, but by the end—after Italian beef sandwiches and one last look at those giant faces spitting water in Crown Fountain—I felt like I’d gotten under Chicago’s skin a little bit. Oh, right: your ticket includes a free bike or kayak rental too, which is wild considering how much food you eat (not sure I could’ve pedaled anywhere right after). Still thinking about that view from Millennium Park though…

What’s included

Your day includes guided walking through central Chicago with all tastings—deep-dish pizza, classic hot dog, Italian beef sandwich, dessert (brownie or gelato)—plus insider stories from your local guide as you visit landmarks like Millennium Park and State Street. You also get a free two-hour bike or kayak rental to use within three days of your tour date.

Good to know

Easy physical levelWheelchair accessibleAccessible transportStroller friendlyPublic transport nearby

Operated by Bobby's Bike, Hike & Food Tours - Chicago