Chicago: Downtown Pizza Guided Walking Tour with Tastings

If you’re a pizza lover heading to Chicago, this tour might just become one of your favorite food memories. We haven’t done it ourselves, but based on the glowing reviews and detailed description, it sounds like a satisfying way to get a true taste of what makes Chicago a pizza destination. This 3-hour guided walking experience takes you through the city’s historic downtown pizzerias, showcasing everything from classic deep-dish to artisanal Neapolitan pies.

What we really appreciate about this tour is the focus on variety and the educational aspect—a chance to understand not just what you’re eating but why it tastes the way it does. Plus, having preordered pizzas waiting for you at each stop means no awkward ordering or waiting around. One thing to consider: it’s a walking tour, so comfortable shoes are a must, and if you’re not keen on walking, this might not be ideal.

This tour is perfect for foodies, first-time visitors, and Chicagoans who want a fun, relaxed way to explore the city’s pizza scene. Whether you’re traveling solo, with friends, or even as a couple, it offers a blend of history, great conversation, and, of course, delicious slices.

Key Points

• Diverse pizza styles: Tour includes Neapolitan, Detroit, tavern, and deep-dish, offering a broad taste of Chicago’s pizza diversity.
• Educational experience: Learn about pizza ingredients, history, and the physics behind the baking process.
• Convenient seating: Pizzas are preordered and waiting for you at each stop, saving time and making the experience more relaxed.
• Small group setting: Expect a friendly, humorous guide leading the way, making it easier to ask questions and enjoy the journey.
• All ages welcome: Suitable for most fitness levels, and the food acts as a filling lunchtime or early dinner.
• Great for photo opportunities: The tour’s route provides chances to snap photos of Chicago’s vibrant downtown.

You can check availability for your dates here:

An In-Depth Look at the Chicago Pizza Tour

When you consider the cost of $73 per person, this tour offers a lot of value. Not only do you get four tastings, but also the insight of a knowledgeable local guide who shares stories and facts about Chicago’s pizza culture. From the outset, the meeting spot at Roberts Pizza is central, nestled between Navy Pier and the Magnificent Mile, making it easy to include in your broader city itinerary.

The Itinerary and What You’ll Experience

The tour kicks off with a visit to a highly-rated artisanal pizzeria, where you’ll sample a slice that highlights craftsmanship and fresh ingredients. The guide will explain the unique characteristics of this style of pizza—what makes it different from others, and why it’s so well-loved. The emphasis on preordering means your pizza is ready and waiting, so no need to worry about long waits or unclear menus.

Next, you’ll move to a second stop featuring a Chicago deep-dish. Many travelers assume deep-dish is the only style Chicago is known for, but this tour clarifies that Chicago’s pizza scene is much more varied and nuanced. The guide dispels some myths—like deep-dish being the preferred style—and introduces you to other styles like tavern and wood-fired pizzas.

The third stop might surprise you with a Detroit-style pizza, renowned for its thick, crispy edges and airy interior. It’s a great way to experience a regional variation that’s not as commonly found outside the Midwest. The fourth and final stop wraps up with a Neapolitan slice, offering a more traditional, delicate crust and simple toppings that showcase Italy’s influence on American pizza.

Why This Tour Stands Out

One of the best aspects, according to reviews, is the informative, humorous guiding style. Our sample reviews praise the guide’s depth of knowledge about dough, ingredients, and pizza history, making the experience not just about tasting but about understanding. As one reviewer noted, their guide “has done his research about pizza dough and the history of pizzas,” which adds a layer of context that elevates the experience beyond just eating.

The small group size fosters a more intimate, relaxed atmosphere, allowing plenty of time for questions and photos. The tour is suitable for all ages and fitness levels—although it involves walking about a mile, which is manageable for most people.

The Food and the Experience

Each pizza is carefully selected to showcase different styles and flavors, giving you a well-rounded pizza education. The tastings amount to a satisfying lunch or early dinner, making this tour a practical option if you want to combine sightseeing with food.

Reviewers mention the quality of the pizzas varies slightly, with some noting that the overall experience is fun and educational but perhaps not the absolute best pizza they’ve ever had. Still, the variety and storytelling more than compensate, creating a memorable experience.

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Practical Details and Value

The price of $73 includes all four tastings, reserved seating, and the guide’s expert commentary. That breaks down to a reasonable cost per slice considering the location and the guided nature of the tour. Drinks aren’t included but are available for purchase, which is typical. The reservation and free cancellation policy offers flexibility—reserving now and paying later is a nice perk if your plans are still flexible.

The tour departs rain or shine, and given Chicago’s unpredictable weather, it’s wise to dress appropriately and wear comfortable shoes. The leisurely pace ensures you’re not rushed, and the route is designed for easy walking.

Who Will Love This Experience?

This tour is a hit for foodies curious about Chicago’s pizza scene. It’s also great for travelers wanting a mix of history and tastings without committing to a full sit-down meal. If you enjoy learning about local culture through food, this tour will resonate.

While it’s not tailored for those with mobility impairments—since it involves walking—most others will find it accessible and enjoyable. It’s an especially good choice for first-time visitors wanting a fun, relaxed way to explore the downtown area.

Final Thoughts

In the end, this Chicago Downtown Pizza Guided Walking Tour offers a tasty, educational escape into the city’s pizza culture. The combination of expert guides, diverse styles, and reserved seating makes it a convenient and satisfying way to spend a few hours in the city.

If you’re a pizza fan eager to understand Chicago’s unique take on this beloved food, or simply looking for a fun food tour that balances flavor with insight, this experience fits the bill. It’s especially recommended if you enjoy strolling through vibrant city neighborhoods, sampling small bites, and learning as you go.

While it might not be the place for a serious pizza connoisseur seeking the absolute pinnacle of pizza quality, it’s a well-rounded, fun introduction to Chicago’s pizza landscape that most travelers will find worthwhile.

Frequently Asked Questions

Is the tour suitable for all ages?
Yes, the tour is suitable for all ages and fitness levels, as it involves about one mile of walking and tastings that act as a meal.

Do I need to bring anything special?
Just your passport or ID, comfortable shoes, and weather-appropriate clothing. Luggage or large bags aren’t allowed.

What’s included in the price?
Four pizza tastings, a knowledgeable guide, and reserved seating at each of the four pizzerias.

Are drinks included?
No, drinks are not included but are available for purchase at each stop.

How long is the tour?
It lasts approximately 3 hours and departs rain or shine.

Where do I meet the guide?
At Roberts Pizza in downtown Chicago, ask the host for the Chicago Pizza Tour.

Is this a good tour for a solo traveler?
Absolutely, the small group setting and friendly guide make it easy to meet fellow travelers and enjoy the experience.

What if I want to cancel?
You can cancel up to 24 hours in advance for a full refund, making it a flexible booking option.

If you’re looking to combine this with other Chicago adventures, consider booking a river cruise or visiting the city’s top attractions afterward. But for a satisfying, no-fuss taste of Chicago’s pizza, this tour delivers in both flavor and fun.

You can check availability for your dates here: