Secret Food Tour Chicago: Loop District & 6 Tastings｜United States

Discover the bold flavors and rich history of America’s “Second City” on our Secret Food Tour: Chicago. Guided by a local expert, you’ll explore the iconic Loop District, where world-famous architecture meets some of the country’s most legendary foods. Along the way, you’ll enjoy 6+ tastings that showcase the culinary traditions shaped by the people who built this city.

Our journey begins with a visit to one of Chicago’s cultural landmarks, the Harold Washington Library, before diving straight into one of the city’s favorite snacks - freshly popped gourmet popcorn, famously listed as one of Oprah’s “favorite things.”

Next, it’s time to sink your teeth into a true Chicago classic: the Chicago-style hotdog, piled high with traditional toppings (but never ketchup!). We’ll continue with a Secret Dish, enjoyed inside the former tallest building in the world, an unforgettable bite tied to the city’s storied skyline.

Of course, no Chicago food tour would be complete without the Italian beef sandwich, thinly sliced, perfectly seasoned, and dipped for that juicy, savory finish. Then comes the crown jewel: a slice of deep dish pizza, a creation so hearty and delicious it’s become synonymous with the city itself.

Finally, we’ll end on a sweet note with a dessert born right here in Chicago—the brownie. You’ll hear the story of its invention while indulging in a modern version of this iconic treat.

As you walk through the Loop’s bustling streets, surrounded by stunning skyscrapers and public art, your guide will weave together the stories of how immigration, innovation, and resilience shaped both Chicago’s skyline and its food scene.

Please note: the itinerary and menu may vary depending on availability and seasonality.

THE FOOD

• Classic deep-dish pizza with sausage

• Freshly popped gourmet popcorn

• Authentic Chicago-style hot dog

• Savory Italian beef sandwich

• Decadent chocolate brownie

• Our surprise Secret Dish

THE DRINKS

• Water