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Discover Chicago’s best eats and iconic sights on a private 3-hour walking food tour, including deep-dish pizza, hot dogs, and architectural highlights.

The Chicago Private Walking Food Tour with Secret Food Tours offers a personalized way to experience the city’s vibrant food scene and stunning architecture. Priced at $306 per person, this 3-hour tour is best booked 33 days in advance and departs from 400 S State St, ending across the street from Millennium Park. It’s ideal for those who appreciate both delicious bites and cultural insights, with a private experience that allows for flexibility and individual attention.
This tour is particularly well-suited for travelers who want to combine food tasting with a walk through downtown Chicago’s most famous sights. The tour includes a generous lunch of Chicago-style favorites, with enough samples to serve as a substantial meal. While it’s rich in food and history, it’s also important to note that participants should have a moderate physical fitness level due to walking and some standing.
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The itinerary begins at Ginos East, known for its classic deep-dish pizza, where participants enjoy a slice of sausage pizza that’s hearty enough to substitute for lunch. From there, the guide leads you through the Loop, visiting prominent landmarks and sharing stories behind them. Stops include the Chicago Public Library, a symbol of the city’s architectural excellence, and the Federal Plaza, home to Calder’s Flamingo sculpture.
This walk covers some of Chicago’s most recognizable buildings, like the Willis Tower, which for many years held the title of the tallest building in the world. The Skydeck offers memorable city views, and the tour provides brief walks around the Rookery Building and Palmer House Hilton, both representing Chicago’s resilience and history. Each stop offers a chance to appreciate the city’s architectural prowess and learn fascinating facts.

A standout feature of this tour is its emphasis on the city’s architecture. The Willis Tower stands tall as an emblem of Chicago’s skyline, with its black aluminum and bronze-tinted glass exterior. The Rookery Building showcases late 19th-century design, reflecting Chicago’s rebuild after the Great Fire of 1871. The Federal Plaza, with Calder’s Flamingo, adds an artistic element to the walking route.
The guide’s storytelling about these buildings and sculptures adds depth to the experience. The 20-minute stops here let participants take photos and soak in the urban landscape while gaining insight into Chicago’s design evolution. The financial district on LaSalle Street demonstrates Chicago’s economic importance, with towering skyscrapers forming a striking canyon.

The food part of the tour is designed to showcase Chicago’s most famous dishes. Starting at Ginos East, the deep-dish pizza with sausage is a signature treat. The tour then offers Chicago-style hot dogs, characterized by mustard, onions, pickle, pepper, and celery salt on a steamed bun, along with Italian beef sandwiches, famous for their tender meat and flavorful au jus.
Participants also sample gourmet popcorn and a brownie, rounding out the savory and sweet options. An exclusive secret dish adds an element of surprise for repeat visitors. These samples are generous enough to serve as a lunch, making the tour both a culinary and cultural experience.

Reviews consistently praise the guides for their knowledge, friendliness, and engaging storytelling. Guides like Justin, Sue, and Ben are noted for their ability to weave fun facts about Chicago’s history, architecture, and cuisine into the walk. Their approachable style and flexibility are especially appreciated, with many reviews highlighting their capacity to answer questions thoroughly.
The guides’ passion enhances the tour, turning it into a lively, informative experience. Their familiarity with local food spots and city sights helps visitors uncover hidden details that many overlook, making each tour unique and memorable.
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The tour begins at 400 S State St, a convenient location close to public transportation. It concludes across the street from Millennium Park, giving easy access to additional sightseeing or dining options afterward. The mobile ticket makes checking in straightforward, and the tour runs rain or shine, with a clear cancellation policy offering a full refund if canceled 24 hours in advance.
Participants should be prepared for moderate walking and standing, as the route covers several notable stops on foot. The tour is private, meaning your group enjoys an exclusive experience without strangers, adding to the overall comfort and intimacy.

What sets this tour apart is its combination of food sampling with architecture and history insights. Unlike more generic food tours, this one emphasizes local landmarks and their stories, making the experience more engaging. The private setting allows guides to tailor the experience and answer questions in depth, which many reviews say makes the tour feel personalized.
Another benefit is the generous food portions, which often serve as a full meal, and the hidden spots visited that many visitors might miss on their own. The inclusion of famous Chicago foods—deep-dish pizza, hot dogs, Italian beef—ensures a true taste of the city.

This tour appeals most to food lovers keen to try Chicago specialties while also exploring the city’s iconic architecture. It’s ideal for those who prefer a private, flexible experience rather than group tours. People interested in urban design and history will find the stories behind structures like the Willis Tower and the Rookery Building particularly fascinating.
The pace suits those comfortable with moderate walking and who enjoy a combination of tasting, sightseeing, and storytelling. It’s perfect for visitors who want a comprehensive yet relaxed overview of Chicago’s culinary and architectural landscape in just three hours.
The $306 per person price reflects the personalized experience, generous food portions, and exclusive access to some of Chicago’s most famous landmarks. The tour’s high ratings—a full 5.0 out of 5 from 46 reviews—speak to its consistent quality and the enthusiasm of guides like Justin, Sue, and Ben.
While it doesn’t include hotel pickup or drop-off, the centrally located meeting point makes it easy to join. The flexible schedule and full refund policy provide peace of mind for booking. For those wanting an intimate exploration of Chicago’s food and architecture, this tour offers a balanced, engaging, and satisfying experience.
“Justin was AMAZING!!!! This was a fabulous tour from start to finish. And Justin was the reason. I am telling everyone I know that they should b…”
What is included in the tour?
Participants enjoy lunch, featuring deep-dish pizza with sausage, gourmet popcorn, a Chicago-style hot dog, Italian beef sandwich, brownie, and an exclusive secret dish.
How long does the tour last?
The tour runs for approximately 3 hours, with many reviews noting the pace is lively but manageable for most physically moderate travelers.
Is this tour suitable for people with mobility issues?
The tour involves walking and standing at various stops, so travelers should have a moderate physical fitness level.
Where does the tour end?
It concludes across from Millennium Park, providing easy access to additional sightseeing or transport options.
Can I cancel the tour?
Yes, cancellations are free up to 24 hours before the scheduled start, with a full refund available if canceled within this window.