A Secret Dish Inside Willis Tower, Then the Palmer House Brownie
Three hours in the Loop, eating your way through six Chicago dishes and the landmark buildings that hold them.
The meeting point is a pizzeria counter at 805 South State Street, and the guide is the one holding an orange umbrella. From there a group capped at twelve heads north into the Loop, stopping six times to eat and several more times to look up.
Roughly 45 minutes of the three hours is walking, and it arrives in short stretches between food stops. The guide keeps to the group's pace. The rest of the time goes to eating, and to standing inside buildings that reward the neck strain.
Two versions of this walk sell on the same page. One is the small-group departure, capped at twelve travelers. The other is a private upgrade that runs the route for your own party. Current departure times and pricing sit on the booking page.
Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef SandwichSmall-group walk through the Loop with six tastings. Three hours, twelve travelers at most.www.viator.comThe Six Dishes, From Deep Dish to the Brownie
The list is published in advance: a Chicago-style hot dog, an Italian beef sandwich, deep dish pizza, gourmet popcorn, a fudgy brownie, and one dish the operator withholds until the day of the tour. Water is the drink that comes with it.
The operator calls the whole run a tasting menu and says travelers will not be hungry afterward. The itinerary and menu can change based on what the stops have available, the weather, and other circumstances. That caveat is the operator's own wording, printed under its Chicago listing.
The Stops Are Landmarks You Walk Into
The route threads six landmarks in the Loop. It opens at the Harold Washington Library Center, turns down the LaSalle Street canyon toward the Art Deco face of the Board of Trade, and crosses Federal Plaza, where a Calder stabile stands in front of the Kluczynski Federal Building.
The secret dish is eaten inside Willis Tower, which held the title of tallest building in the world for nearly 25 years after it was finished. The Rookery draws the longest stop on the itinerary at 30 minutes, and its ground-floor light court keeps hours of its own. That lobby opens to the public from 7:00 a.m. to 6:00 p.m. on weekdays and from 8:00 a.m. to 2:00 p.m. on Saturdays, and stays closed on Sundays. The walk ends at the Palmer House on East Monroe Street, whose kitchen is widely believed to be where the brownie was invented.
Twelve Travelers, and About 45 Minutes on Foot
A single seat books on its own. The operator separately asks for at least four guests to run a scheduled departure, and reserves the right to cancel and refund when that number is not met.
Walking arrives in short pieces between the stops, and the guide moves at the group's pace. A traveler who walked it in June 2025 wrote that the guide's detours to lesser-known corners "helped to pace the food intake." Comfortable shoes are the operator's own recommendation.
The operator states that many of its tours are not wheelchair or stroller accessible, and asks travelers to make contact before booking to discuss this one. Children two years and under join at no charge.
Dietary Requests Close Before You Book
Dietary limits are settled before booking. The operator asks travelers to email its Chicago address in advance to find out whether a restriction can be accommodated, and states that many of its tours cannot take certain restrictions.
Cancellation terms differ depending on where the booking is made. Booked through the card on this page, the tour refunds in full when a traveler cancels at least 24 hours before the scheduled departure. The operator's own terms for direct bookings run the other way and treat tickets as non-refundable once an order is accepted. The 24-hour rule is the one that governs a booking made here.
The guide waits at Lou Malnati's Pizzeria, 805 South State Street, under an orange umbrella. Departure times vary by date and appear on the booking page. Gratuities and hotel transfers are not included. The restaurant lists street parking on State Street in front of it, and a garage around the corner on East 8th Street.
The last tasting is a modern version of the brownie at the Palmer House, which leaves the group on East Monroe Street in the middle of the Loop, a few minutes' walk from Millennium Park.