Chicago Guided Tour: Iconic Architecture and Deep Dish Pizza
32 Ratings
Experience the best of Chicago with our guided tour! Explore iconic architecture and indulge in deep dish pizza and other local treats. Discover the city's history and vibrant food scene.
Duration: 5 hours
Cancellation: 1 day learn more
  • Chicago Pedway - You’ll head into the network of tunnels and bridges that connect skyscrapers and retail stores to see how locals move around the city (especially during those Midwestern winters)!
  • Chicago Riverwalk - If the weather is good, we’ll be able to take a wander down to this iconic river and soak in the views it has to offer. Sights include Marina Towers, the Britannica Building, and the Sears Tower (now known as the Willis Tower).
  • Wrigley Building - You can’t think of Chicago without thinking of the Wrigley Company. This skyscraper with its central clocktower, first built in the early 1900s, no longer houses Wrigley Company, but is home to several other significant businesses and consulates.
  • Tribune Tower - This building represents the core of journalism in Chicago and is home to the newspaper ‘The Chicago Tribune’. Soak in the views of this beautifully picturesque building - which marries two of Chicago’s most well-known industries: journalism and architecture.
  • Water Tower Place - The second half of your tour begins at the extravagent Chicago Water Tower - definitely unlike any water tower you’ve ever seen! A symbol of “old Chicago,” this building survived the Great Fire and, today, houses the Chicago Office of Tourism art gallery. From here you’ll head off on your Chicago food adventure!
  • John Hancock Center - Formerly known as the John Hancock building, this towering skyscraper can be seen throughout Chicago, and at several points on our tour.
  • Downtown / The Loop - Your tour takes place in this lively neighborhood of shopping, nightlife, performing arts scenes, and, of course, restaurants with the best food Chicago has to offer!
What's Included
  • Lunch
What's Not Included
  • Additional food and drink, souvenirs, tips and gratuities for the guide.
Additional Information

Experience all of Chicago by combining our key Chicago Highlights & Architecture Tour and the engaging Chicago Food Tour: From Deep Roots to Deep Dish!

Our dual-part exploration kicks off in the bustling heart of downtown Chicago, featuring its iconic old and new architecture, views of the beautiful Chicago River, the bustling Millenium Park, and vibrant city streets (while also stopping for some delicious local bites).

Next, we proceed to the Central Loop, a spot frequented by residents for their popular food choices, at all hours. Get the authentic Chicago taste and learn about the history and procedures (and the do’s and don’ts) behind the city’s iconic street and comfort foods - ranging from the famous deep dish pizza to diverse sandwiches and a fully loaded hot dog!

Your local guide will dazzle you with intriguing tales and the common immigrant chefs and vendors who contribute to Chicago’s diverse food landscape. At the tour’s conclusion, you’ll walk away with a profound appreciation for both this incredible city’s historical evolution and the significant role food has played in shaping the lives of Chicago’s inhabitants!

175 N State St
North State Street
The Chicago Theatre (under the marquee)
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
(32 Ratings)
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1 star
Nov 14, 2023
Raj @ First time at Chicago - Fun, adaptable, great stories...Will do it again. Promised to this again in summer when the bean will hopefully be ready for the close photoshoot
Review provided by Tripadvisor
Nov 11, 2023
Great walking tour - Kevin was great..funny and insighful...we visited interesting places and finished with the food tour and the taty deep dish pizza
Review provided by Tripadvisor
Nov 8, 2023
Best tour guide ever! - I’ve been to several tours internationally but Chicago Dave’s was by far the best one I’ve ever been to! It wasn’t rigid and robotic. He was lively, personable, and really passionate about his hometown. His love for all things Chicago is palpable and extremely contagious! It’ll make you want to go back and experience more of what the Windy city has to offer!
Review provided by Tripadvisor
Oct 16, 2023
Worthwhile - Dave really enthusiastic and knowledgeable . Learned a lot about buildings, millennium park, food and water. Enjoyed the tour. I will take one earlier in the trip. He gave me ideas for the next trip here
Review provided by Tripadvisor
Sep 19, 2023
A highly recommend your to get to know Chicago - “Chicago Dave” was our guide and he did a great job of conveying his love for and knowledge of Chicago to the tour group. He had fun and informative stories and “brought to life” many of the places that we stopped at during the tour!
Review provided by Viator
Aug 24, 2023
Great work Dash - Our tour guide DAsh was excellent…so knowledgeable and keen to share all his information…. Even though walking in 40 degrees…he made it a memorable event and as pleasant as possible with the heat.. learnt so many fascinating aspects of chicago
Review provided by Viator
Aug 23, 2023
Good Tour - Our tour was good if your into architecture. A lot of walking so wear comfy shoes. Richard was very informative and if he didn't know something he made sure to find out. The food he took is to was ALL DELICIOUS! Overall good day.
Review provided by Viator
Jun 21, 2023
Great Tour - I especially enjoyed seeing the Sullivan and Marquette Buildings. Rich, our tour guide, was very knowledgeable and shared lots of interesting history and stories with us (really liked hearing about the Jewelry Building). The food tour stops were also great and I finally got to experience a real Chicago hot dog (thank-you Rich).
Review provided by Viator
May 11, 2023
Review - Excellent experience, great tour guide, very enthusiastic about the history of Chicago, he answered all questions!
Review provided by Viator
Mar 18, 2023
Chicago re-visited - Dash our tour guide was enthusiastic and very knowledgeable about his home City. This made the tour very enjoyable despite a temperature of -10 degrees. Dash showed us various different buildings from different phases of Chicago's history. I really enjoyed the ride on the Loop.
Review provided by Viator
Select Date and Tickets
up to 12 guests
1 Adult
May 2024