Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

Eat your way through 150 years of Chicago food history in three hours.

A food tour through Chicago's Loop District where you taste six dishes rooted in the city's culinary heritage, including deep dish pizza and an Italian beef sandwich, while passing the Rookery Building, Palmer House Hilton, Willis Tower and other architectural landmarks. The tour involves a fair amount of walking; a live English-speaking guide leads the group and reveals a secret dish on the day itself. Choose between a private tour or a small group option at checkout.

Step-by-step itinerary

Chicago food and architecture tour

• Walk through Chicago Loop District
• See African American Mayor memorial
• Explore LaSalle Street financial district
• View Calder's Federal Plaza sculpture
• Admire Willis Tower exterior
• Visit Rookery Building
• Discover Palmer House Hilton history
• Taste deep dish pizza and Italian beef sandwich
• Enjoy gourmet popcorn and secret dish

The Experience

Six dishes across three hours means you're moving between stops, tasting as you go. You'll start with a fudgy brownie and a Chicago-style hot dog, then move into the heavier hitters—the deep dish pizza and Italian beef sandwich that define the city's food identity. Gourmet popcorn and the secret dish round out the menu, each one tied to a piece of Chicago's past. The operator notes that many of these dishes have roots dating back over 150 years, so you're eating history as much as lunch.

The walk threads through the Loop District, where you'll pass the Rookery Building—a late-nineteenth-century office tower that rose after the Great Fire of 1871—and the Palmer House Hilton, built by the business magnate who shaped downtown State Street. You'll see the Willis Tower, which held the title of world's tallest building for nearly 25 years, and the 53-foot Calder stabile in Federal Plaza. The architecture and public art are woven into the route, not separate from it; the food stops and the landmarks move together.

A live guide in English leads the way and knows which restaurants and vendors are part of the tour that day. The menu and itinerary can shift based on location availability and weather, so the operator asks that you contact them in advance if you have dietary requirements—they'll work to accommodate them. Comfortable shoes matter here; the three hours involve a fair amount of walking, and you'll be on your feet between tastings.

What’s included

• Fudgy brownie.
• Chicago-style hot dog.
• Italian beef sandwich.
• deep dish pizza.
• gourmet popcorn.
• secret dish revealed on the day.
• live English-speaking guide throughout the three-hour walk.

Good to know

Easy physical levelNot for heart conditions

Operated by Secret Food Tours

Is this one for you?Book the private option if you want the route and timing to yourself; the small group tour works well if you're comfortable sharing the experience and want to meet other food travelers in Chicago.

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Top questions

What exactly is the secret dish on the Chicago food tour?

The secret dish is revealed only on the day of the tour itself, so you won't know what it is until you arrive. It's one of the six items included in the tasting.

How much walking is involved in the three-hour food tour?

The tour involves a fair amount of walking through the Loop District, so comfortable shoes are essential. You'll move between food stops and pass landmarks like the Rookery Building, Willis Tower and the Palmer House Hilton along the way.

Can the tour accommodate dietary restrictions?

Yes, contact the operator in advance of the tour to discuss any dietary requirements, and they'll work to cater for them. The menu is also subject to change based on location availability and other circumstances.

What is the Rookery Building and why does it matter to Chicago's story?

The Rookery Building stands in Chicago's financial district and was built in the late nineteenth century after the Great Fire of 1871. It represents the city's resilience and became a model for the multi-story office buildings that transformed American cities.

Is hotel pickup included in the food tour?

Hotel pickup and drop-off are not included. You'll meet the guide at the starting point in the Loop District.

Can I book this tour as a private experience or only with a group?

You can choose between a private Chicago food tour or a small group food tour at checkout. Both follow the same route and include the same six dishes.