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Chicago Highlights: Architecture & Food Tour
4.9
957 Ratings
Chicago
Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treat and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!
Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treat and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more!
Duration:
5 hours
Cancellation:
24 hours
Highlights
- The Chicago Theatre - The tour kicks off beneath the sparkling marquee of the Chicago Theatre, a cinematic icon, before venturing into the vibrant city streets.
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Chicago Pedway - If the weather is favorable, the tour will explore the Chicago Pedway, an underground tunnel network frequented by locals and commuters, especially during winter.
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- The Chicago Theatre - The tour kicks off beneath the sparkling marquee of the Chicago Theatre, a cinematic icon, before venturing into the vibrant city streets.
- Chicago Pedway - If the weather is favorable, the tour will explore the Chicago Pedway, an underground tunnel network frequented by locals and commuters, especially during winter.
- City of Chicago - City Hall - The tour will pass by the City Hall-County Building, which houses the City of Chicago and Cook County governments.
- Chicago River - Experience the local vibe while walking past iconic buildings, enjoying breathtaking skyline views, and joining the daily commute along Chicago’s main thoroughfare.
- Wrigley Building - The tour will then pass the Wrigley Building on the Magnificent Mile, constructed between 1920 and 1924 as the Wrigley Company’s headquarters.
- Tribune Tower - Next, the tour will pass the Tribune Tower, a 463-foot, 36-story neo-Gothic skyscraper located at 435 North Michigan Avenue.
- Millennium Park - The tour will visit the scenic Millennium Park, home to the famous Bean sculpture. The guide will provide recommendations for additional sights, dining options, or drinks.
- Cloud Gate - The tour will pass the Cloud Gate sculpture, also known as ‘The Bean,’ the highlight of Millennium Park.
- River North - During the culinary portion of the tour, participants will enjoy a classic Chicago-style hot dog, followed by the renowned deep-dish pizza. After savoring these, one more local favorite will be sampled before concluding with a traditional Italian beef sandwich at a genuine Chicago establishment.
- Historic Water Tower - The tour will then pass the charming Water Tower, built in 1869 to house a water pump drawing from Lake Michigan. It is the second-oldest water tower in the United States.
- The Loop - Finally, the tour will stroll through the main streets near the Loop, where museums, restaurants, bars, historic landmarks, and modern architecture seamlessly blend.
What's Included
- Learn about Chicago’s rich history from a local expert guide
- Taste iconic Chicago foods: hot dogs, deep-dish pizza, and Italian beef.
- Walk through the historic Chicago Theater, a city icon
- See the famous Cloud Gate sculpture in Millennium Park
- Use local transportation to travel between the two halves
- Enjoy some classic Chicago-style popcorn…
- Learn about Chicago’s rich history from a local expert guide
- Taste iconic Chicago foods: hot dogs, deep-dish pizza, and Italian beef.
- Walk through the historic Chicago Theater, a city icon
- See the famous Cloud Gate sculpture in Millennium Park
- Use local transportation to travel between the two halves
- Enjoy some classic Chicago-style popcorn
- Get tips on more sights, activities, and dining during your stay.
- Join a professional, English-speaking local guide
- Stroll the Chicago Riverwalk with stunning views of skyscrapers
What's Not Included
- Gratuity
- Drinks and additional food
- Gratuity
- Drinks and additional food
Additional Information
- This is a child-friendly walking tour. Children under the age of 6 are permitted to join this tour free of charge.
- Please note: food options and portion sizes will vary depending on the season and where we stop that day but the total amount of food included will be equal to a full meal.
- Suitable for all ages and fitness levels, but please note that…
- This is a child-friendly walking tour. Children under the age of 6 are permitted to join this tour free of charge.
- Please note: food options and portion sizes will vary depending on the season and where we stop that day but the total amount of food included will be equal to a full meal.
- Suitable for all ages and fitness levels, but please note that this tour covers between 4.8 to 6.4 km (3-4 miles) of walking.
- We can accommodate vegetarian options but cannot accommodate other food allergies or dietary preferences. Please notify us in advance if you have any dietary requests.
- Experiences happen rain, shine, or snow. Please dress accordingly.
Location
The Chicago Theatre
North State Street
The Chicago Theatre (underneath the marquee), 175 N. State Street, Chicago, IL 60601
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
4.9
(957 Ratings)
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Charlot2510
Feb 14, 2025
Excellent tour with our top guide Dash! - Dash was our guide. He talked about Chicago with enthusiasm and passion.
He made sure we never got cold.
We saw many buildings on the outside. This was cool. But what makes these buildings really beautiful is their insides. Beautiful architecture!!
Along the way we enjoyed popcorn, brownie, hot dog and sandwich. Dash kept the best for the end. Delicious fresh pizza!
We had a great day and got to know Chicago!
Thank you Dash!
Review provided by Tripadvisor
Chris_l
Feb 10, 2025
Chicago tour was amazing - My friend and I had a most excellent tour of Chicago. Loved the food and locations we visited. The tour guide Chicago Dave was a blast and very knowledgeable. I asked one question at the beginning and totally fulfilled our request.
Review provided by Viator
Gary_k
Feb 2, 2025
Well worth the time and money! - David was awesome! Friendly, knowledgeable, well prepared, spent time with with all the guest at various times. He treated us as “his guest” and even at the end of the tour, when he was “off the clock”, walked us back to one of our locations! Really enjoyed the day!
Review provided by Viator
Jamie_v
Feb 2, 2025
The real Chicago experience. - Our guide was very knowledgeable. All of the stops on our tour were great and the food we had was amazing.
Review provided by Viator
Laura_s
Jan 27, 2025
Fun Day in Chicago made easy! - Very interesting tour, where we covered a lot of ground, but it was made to seem easy. Fun food and places to start, then, yummy dogs, Italian beef and pizza to end. Rich was great and we enjoyed meeting our other new friend Jonathan on the tour as well! We had a lot of fun.
Review provided by Viator
Shadowx289
Jan 25, 2025
5 stars - Our tour guide, Dash, was absolutely incredible! This was easily one of the best tours I’ve ever experienced. I was initially skeptical about the walking and the amount of history Chicago might offer, but I was completely blown away. The city is rich in history and culture, and Dash brought it all to life with his amazing energy and enthusiasm.
The pace of the tour was perfect—not too fast, not too slow. Dash ensured everyone was comfortable and engaged the entire time. Lunch was another highlight—absolutely delicious! His depth of knowledge was remarkable, and he answered all of our questions with such ease. The combination of indoor and outdoor experiences made the tour even more dynamic and interesting.
The train ride was an unexpected but beautiful addition to the tour, making it even more special. Because of Dash and this fantastic experience, I’ll definitely be bringing my family back to Chicago. I’m so grateful for this unforgettable adventure—thank you, Dash!
Review provided by Tripadvisor
R9411dkryanb
Jan 23, 2025
thanks Dash - Dash was great as was the food and the tour. He really knows his architecture and history. He also just has an infectious and contagious energy that made an already wonderful day and trip all the better.
Review provided by Tripadvisor
Matt
Jan 20, 2025
Fascinating and entertaining tour which really helped me understand Chicago. Would recommend! - Our guide, Dash, did a fantastic job. I would recommend this tour to anyone wanting to get a better appreciation for Chicago's history and uncovering some gems downtown. Dash was also excellent at suggesting things to try after the tour. He was so enthusiastic, passionate and knowledgeable about Chicago and clearly enjoyed helping us learn about it. He was also very mindful of group needs, especially as it was so cold, making sure everyone was ok and seeing things that interested them. I was in a tour with 6 others but was able to ask any questions along the way (which Dash always seemed to have answers to and which would lead us into all sorts of fascinating info about Chicago). Expect a mixture of Chicago history, architecture (which Dash used to bring Chicago's history alive), and familiarisation with downtown Chicago and some of its hidden gems. We also got a good overview of surrounding neighbourhoods (even though there is no time to take them all in). Would recommend!
Review provided by Tripadvisor
Happiness37770740492
Jan 19, 2025
An amazing experience! - This was an amazing tour! Getting to see sights I would have simply walked by if I was on my own, and hearing the history of the buildings in Chicago was a joy. Our guide, Dash, was absolutely amazing and did a fantastic job working around the horribly cold weather, and our accommodations. I would HIGHLY recommend you request him for you tour, and will recommend him to my family, friends and clients when they visit Chicago.
Review provided by Tripadvisor
Katiejg3682da
Jan 19, 2025
Phenomenal!!!! - Dash was absolutely phenomenal!! Even though it was a whopping 6° outside, he was friendly, passionate, excited, extremely knowledgeable, polite, and courteous throughout the entire day. Since it was so cold out, he made sure to keep checking on us and completely changed his normal tour route to accommodate our group so we didn’t get too cold. He is extremely good at his job and you can definitely tell how much he loves Chicago. As a person who is interested in art, music, architecture, history, AND food, it was very beneficial to be led around by a native on our work trip since my family and I plan on coming back for a longer stay when it is warmer. As travel agents, he gave us plenty of information not only on the history of Chicago, but also upcoming activities, attractions such as museums and the best restaurants and nightlife, as well as Chicago’s best kept secrets. He also made sure to walk us back to our hotel since we were kind of turned around after taking the train (amazing treat btw since one person in our group had never been on a train before). I will definitely be requesting him when my family comes later this year so they can experience what we did today!! Thank you Dash!! You made the day so enjoyable even though it was bitterly cold!!!
Review provided by Tripadvisor
