moderate
5–6 hours
Suitable for individuals with moderate fitness capable of sustained walking and standing for several hours.
Discover Chicago’s iconic architecture and vibrant food scene on a private day-long walking tour. Experience historic landmarks and local flavors that define the city’s rich culture and urban spirit.
From $545 | 5 Hours | Explore Chicago's most iconic sites!
Inclusions: Local guide and a variety of food samples (such as a slice of deep dish pizza, a sample of local street food, a sweet treat, and a bite of an additional Chicago classic). Food options and portion sizes vary - total amount of food equals a full meal.
**Exclusions:**Additional food and drink, souvenirs, tips and gratuities for the guide.
Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish!
Our two-part tour begins by exploring the heart of downtown Chicago - with its iconic architecture, both old and new, views of the Chicago River, picturesque Millenium Park, and bustling city avenues (plus, a couple tasty local treats along the way).
From there, we’ll hit the Central Loop, where locals go to grab their favorite foods, day and night. Try the best of Chicago fare and get to know the history and how-tos (and how-not-tos) behind iconic street and comfort food staples - from the infamous deep-dish pizza to sandwiches to a loaded hot dog!
Your local guide will entertain with fascinating stories and the everyday immigrant chefs and vendors responsible for Chicago’s eclectic food scene. By the end of the tour, you’ll have a deep appreciation for both the evolution of this excellent city and the role food has played in the lives of all Chicagoans!
This tour involves multiple city blocks of walking on paved surfaces, so sturdy footwear is essential.
Carry a water bottle as you’ll be on foot for several hours with limited stops for drinks.
Chicago’s weather can change quickly; dress in layers especially in spring and fall for comfort.
The city’s architecture and street scenes offer fantastic photo opportunities at every turn.
Chicago’s Loop district was laid out in the late 19th century and grew to be the largest commercial hub in the Midwest, showcasing a history of architectural innovation following the Great Chicago Fire of 1871.
Local tours emphasize responsible tourism by encouraging walking and support of small businesses, minimizing environmental impact in this urban setting.
To ensure comfort over extended periods of urban walking.
Perfect for carrying water, camera, and any personal items during the tour.
Stay hydrated throughout the walking tour.
all specific
Light rain jacket or windbreaker for spring weather variations.
spring specific