The highlight of our first visit to Chicago was our walking tour with Walk Chicago Tours and tour guide Jim. We met at the Chicago Cultural Center and from there spent 3-1/2 hours learning about, and seeing, the great history and architectural wealth that Chicago offers. It was especially fun to pop in and out of the various buildings (that... More

I've visited Chicago several times for both business and pleasure each time seeing a piece of the puzzle but not getting a feel for how the pieces fit together. During my most recent visit with friends we decided to take a walking tour. We chose walk Chicago because the 5 of us could have a private tour with an knowledgeable... More

I just experienced the loop tour downtown with this company and was very impressed. Most of the guides are lifelong Chicago residents who love the city and have great stories to tell. Our guide, Jim, was a retired school teacher and gave my students and I a great tour. In the past I have avoided tours, considering them something for... More

My Italian mother was coming to visit. No one does tours of Little Italy any more except for Walk Chicago Tours. Since the tour was full Terry nicely gave me his directions for free since the tour was booked up for Spring Break to help my mom out. This is an example of a tour service going above and beyond... More

We just returned from a four-day winter trip to Chicago. One day we did a three hour walking tour in the downtown area and on the second day a two hour walking tour in Little Italy. The guides were excellent, well-informed and fun to be with. We were so wrapped up in the experience that we never felt the cold.... More

We spent the weekend in Chicago and my partner, being a history buff, wanted to take a walking tour of Chicago. We met Terry, our guide and the owner of the company, and for the next 3 hours I was captivated on every word out of his mouth. The amount of information that this man knew was incredible!! From dates... More

We were only going to be in Chicago for one day and wanted to see the highlights - I had to convince the three other people with me to go on a walking tour in the chilly Chicago wind, but we all left thinking it was the best thing we did in town. Terry was accommodating from the very beginning... More

My wife and I were spending 2 days in Chicago in September, 2012. Terry Sullivan, the owner of this small tour company, met us at the Chicago Cultural Center on Michigan Ave. and proceeded to give a wonderful walking tour that included the architecture, art, history, and public art/parks of Chicago. Terry had a number of great stories and historical... More

Our tour group was 6 women from Montreal, keen to learn as much as was possible in a short time in the Millenium Park area! Terry O'Sullivan certainly was able to keep us captivated with his anecdotes and historical perspective....His humour, and his obvious passion for his city, made our 3 hours with him a real adventure and pleasure. Not... More