Chicago In A Day Walking Tour: Food, History & Architecture

Tour was great - gave us our bearings and helped to plan rest of the trip! Dash was knowledgeable and enthuasiasti!

Dash is an amazing tour guide. Very enthusiastic about Chicago. Totally recommend this tour had lots of fun. The food at the end was amazing.

The guide was informational, entertaining and wonderful to spend part of a day with strolling along looking at Chicago’s architectural wonders while eating a whole bunch of good local food

What a perfect way to spend a day in Chicago! I'd never been to the city before and was overwhelmed with suggestions of what to do and where to eat, etc...then I found this tour that combined it all. As a general rule, I prefer to tour in small groups that don't immediately stand out as tour groups, and this fit the bill beautifully. Dash was an endless vessel of knowledge and passion for the city, genuinely excited to share historical information, stories, and little extra experiences along the way. I could not have asked for a better guide. For anyone looking to knock out a ton of Chicago in 4.5 hours, I cannot recommend this tour enough. Thank you, Dash!

It was enjoyable. Was about 4 miles of walking total but easy walking. Saw some cool architecture and had some good Chicago food. Rich was very pleasant and clearly wanted us to enjoy the tour.

Our guide, Dave, was amazing. Great tour to see the hidden gems of Chicago. This was my third trip to Chicago and I felt like I was seeing sites all anew.

It's a lot of walking so be prepare accordingly, but also prepare to see breathtaking architecture and informative history of Chicago.

Dave was an excellent guide, just a fountain of knowledge, easy to talk with. He gave good advice on navigating the cta. Overall, just a wonderful experience.

This was an amazing experience! You get to learn all about the structure, art, and history of Chicago. Dash was an amazing guide. He was very knowledgeable and told us the amazing history about the buildings and all of Chicago. I would recommend this tour to anyone who is visiting Chicago and wants to explore the city and what it has to offer.

The tour with Chad was fantastic. He was very knowledgeable and took us to some very interesting places that I was not expecting! We always remember this day!!! Thanks, Chad!!! Evan Thurm

Very fun! We learned a lot of random fun facts, I feel prepared for the next trivia show!

Chad was amazing. So much knowledge and so fun to converse with. The tour was informative and delicious. Highly recommend!

What a fantastic experience! Dave was an outstanding guide who made our Chicago food tour fun, memorable, and absolutely delicious. The food was amazing, and it was such a great way to explore Chicago, discover local favorites, and learn more about the city along the way. Dave’s knowledge, personality, and enthusiasm really made the tour special. He created a welcoming atmosphere, kept everything interesting, and made the entire experience feel personal rather than just another tour. Every stop offered something delicious, and the combination of great food, local history, and wonderful company made for an unforgettable experience. I highly recommend this tour to anyone visiting Chicago or even locals who want to experience the city in a new way. If you get the chance to tour with Dave, don't hesitate — you'll be glad you did! Five stars all the way!

Dave was informative, and the tour was great. I learned a lot about Chicago from this tour!

Holy moly. What a great guided tour of Chicago. Learned so much and it was so enjoyable. Would highly recommend Dash as a guide. Even showed us how the trains work and took us on the Loop. Really enjoyed the day.

We absolutely loved our Chicago in a Day Walking Tour! Kevin was such an amazing guide – super knowledgeable, genuinely funny, and just a great person to spend the day with. He knew so much about the city and also gave us some fantastic tips and recommendations for the rest of our stay. We really enjoyed the food stops too, which made the whole experience even better. We had such a fun day and couldn’t have asked for a better introduction to Chicago. Thanks again, Kevin!

Excellent tour with Rich! Lots of interesting details about Chicago architecture during the 1st half of the tour, and iconic Chicago “eats” during the 2d half. We were a small group of 12, which was a perfect size for the venues we visited.

Dash was great. He is very knowledgeable and could answer many midwestern questions along with the history of Chicago.

Chad was awesome! Very knowledgeable and entertaining. Thanks for a great day!!

Chad did a great job - very knowledgeable and friendly. Thank you!

Awesome experience, great food, learned alot from this tour. Nice seeing all the history

Rich was our guide and was phenomenal! He was super organized, communicated our itinerary prior to our tour and had so much knowledge about the places we visited.

Wonderful and complete tour! Did things i wouldn't have done or tried otherwise. Would highly recommend. Dave was our guide and you could tell how much he loves the city!

Rich was our Tour Guide. You could tell he was passionate about his work. Very knowledgeable, patient, and knew his way around the food part of the tour with connections at the places we visited. Thank you Rich for a nice tour and taste of Chicago.

Fabulous walking tour which covered all the major buildings and great food too. Loved the deep dish pizza at Lou’s, beef at Luke’s and of course, Garretts popcorn to nibble on. Dash, our tour guide was exceptional - funny, friendly and so very knowledgeable. I love how he indulged our questions and gave us all the information we needed. Also just mention: he’s a great photographer. So many wow factors in this tour. Would definitely recommend it

Such an amazing and educational tour of Chicago!!! So well planned and the food was delicious and complemented the tour so well!! Must do when in Chicago!!

Dash was a great guide. Great food and great information. So much interesting information!

Wealth of great Information!

We went on a walking and food tour today with Dash... he was so informative and engaging and it was just a fun way to spend the morning. Dash made the tour very special. Thank You !!

It was a good experience and saw a decent amount of chicago. Would have liked a little more information And depth. The food tour portion was just okay. Great tour guide.

The tour was the best Foodie and Architecture tour I've taken in my three times in Chicago. I liked how we were taken the area across the River and got a large piece of Chicago Pizza, Chicago Hot Dog and Chicago Wet Beef Sandwich. We also got to see the sights within the city.

This was my first trip to Chicago, and our tour guide Chad was awesome in knowing the history behind some of the most beautiful buildings. It’s awesome getting to walk to many attractions that were on the walk. Great tour, wear comfortable shoes for the all the walking!

Had a great experience with this tour, and Chad was an excellent tour guide, he was extremely knowledgeable! Saw so much of Chicago in the time we had and got to try some Chicago staples. I would highly recommend this tour!

Our guide (Chad) was very entertaining and knowledgeable. It was a great way to experience the city - highly recommend!

Rich is a great guide. He is knowledgeable and helpful. We really enjoyed this trip especially the architecture and deep dish pizza. Loved learning about Chicago from Rich.

Loved our guide Dash enthusiasm and knowledge. We visited historic buildings which without our very knowledgeable tour guide Dash we would never found or knew the story linked with these buildings. Great experience and a must do tour especially with Dash as your guide.

I could not have asked for a better tour or Guide. Dash was knowledgeable, personable, and incredibly enthusiastic about his great city. Chicago can easily sell itself, and it did. This tour provided an amazing welcome to the city. I highly recommend this tour and our guide. Thanks for a great day.

Do not hesitate to book this tour! Our guide Dash was extremely knowledgeable and friendly. We found out lots of interesting facts you would otherwise miss just walking around. A great way to see the city - we had an amazing time! Food was delicious too!

Dash was a PHENOMENAL tour guide. He was passionate, knowledgeable, entertaining, and made exploring this beautiful city so much fun! Even my teenagers loved my hearing his stories and learning about the history of Chicago. We will absolutely recommend this tour to everyone we know because of Dash!!

Our guide Dash was so amazing!! He was very entertaining and made learning about the different buildings so interesting!

Our tour guide Dash was amazing! He told detailed, entertaining stories about the city, and he was clearly very genuinely passionate. He was kind, personable, and funny, and he made our experience very enjoyable!

We took the private tour with Kevin and could not have asked for more. He was very friendly, knowledgeable, and gave us great suggestions on other things to do while in town.

Thank you Dave for a wonderful tour. The foods were great choices.

Extremely knowledgeable and friendly guide. Appropriately combined architecture, food, and history. Great way to learn about the city. Weather was perfect.

My friends & I enjoyed the Food, History, & Architecture walking tour. I highly recommend this tour. Our tour guide, Dash, was a wealth of information & made the tour so interesting & fun! We learned so much about this beautiful city! We were treated to the 3 foods Chicago is known for, the Chicago dog, the Italian beef sandwich, & deep dish pizza. We also took a ride on the L & walked thru some beautiful buildings & shops. Thanks to Dash for the awesome recommendation, after the tour we went to a gorgeous rooftop bar to enjoy a beverage & toast to our perfect day!

Great overview with travel through and to some iconic and not too miss areas in the city. Great narration with interresting facts and information. Good pace. Tasted and stopped at Chicago's best for popcorn, hotdog, pizza and Italian beef. Chad was a great guide and did a fantastic job. Highly recommend this tour!!

Had a great tour with Chad. He is super knowledgeable and made the day enjoyable.

Awesome tour! Chad was excellent with showing us all the hidden gems, providing informative narration all along the way and answered every question with thorough personal experiences. He did a fantastic job! We saw great sights all along the way and ate local iconic foods. Highly recommend this tour to get a great tour and food!

Chad was our tour guide and did a fantastic job. Very personable, knowledgeable and friendly guide. He made the experience fantastic and I would highly recommend him.