Illinois
Winding Through the Windy City: Art & Architecture in Chicago
Program No. 21908RJ
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Winding Through the Windy City: Art & Architecture in Chicago
Winding Through the Windy City: Art & Architecture in Chicago
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Participant Reviews
Based on 41 Reviews
SHOWING
A+ all the way around!
— Review left October 5, 2025
Excellent way to see Chicago. Want to take another tour there to see even more.
— Review left October 5, 2025
It was my first experience with Road Scholars. I am almost 82 years old and a widow, and I was so pleased to meet other solo travelers my age, with whom I had much in common. It was SO refreshing! I would highly recommend travel with Road Scholars.
— Review left August 13, 2025
This journey was an amazing time that gave me the opportunity to explore an entire city I've never been to before with comfort and sense of security. Wonderful talks with local historians and people who are proud of this city of Chicago who toured with us and narrated the journey.
The location of the hotel was also a great resource for free exploration, the riverwalk was just two blocks away offering a refreshing walk before a good night sleep. The eateries are many and you can find the talked about Chicago dog and pizzas that were famous. The Road Scholar tour and the group of friends you meet was a real vacation experience I'm glad I took. And I came home with some memorable pictures to remember for a while.
— Review left July 22, 2025
This trip was fantastic. Andrea Maremont was a fabulous leader. She was very organized and attended to every detail of each activity. She watched out for all of us! Her love of Chicago and her knowledge of its history and architectural treasures was infectious.
I loved the curriculum and scheduled activities. Only one suggestion: having made the trip to Oak Park, it would be a great to see the inside of the Unity Temple.
I approve of the family style approach to meals. Keep that up--maybe adding it to some of the dinners/lunches later in the week.
The location of the hotel, in River North, was ideal--right in the heart of it all. It made our free time activities very accessible.
— Review left July 13, 2025
Terrific trip to Chicago this week!!! I had no idea how many cultural sites were there. It is a beautiful city with a fascinating history. My family really enjoyed this tour!! I learned so much and had a great time doing it. Really good people to spend time with also.
— Review left July 12, 2025
Great trip and tour guide. Bus drivers did a great job navigating the city. All of the instructors were very knowledgeable and informative. Food was fantastic too.
— Review left July 12, 2025
Wonderful, informative trip. Chicago is a great town.
— Review left October 26, 2024
Strong recommendation. Gave me a new appreciation for a signature city.
— Review left July 22, 2024
This was our first trip to Chicago and we had a wonderful time. It's a "new" city, the river cruise showcased the beautiful skyscrapers and architecture. We had a day at the Art Institute and an excellent tour of Frank Lloyd Wright's house. Great group leader (Karen) and great fellow travelers.
— Review left June 17, 2024
Fun way to explore Chicago from a convenient hotel base.
— Review left June 17, 2024
A wonderful way to explore Chicago, known for its museums and architecture. The guide was magnificent and very accommodating. The accommodations were just right. The food was very good. The group was very friendly.
— Review left May 20, 2024
Thrilled to see & participate in how alive and fun Chicago is!
— Review left May 19, 2024
My first time to Chicago and first RS tour ( although have visited numerous countries, cities and continents on my own) . The caliber of the presenters and the program was excellent. The meals were delicious and the itinerary was perfect. Everyone was friendly and interesting ...and was good value for money
— Review left May 11, 2024
I encourage anyone considering this trip to Chicago to see & study its art & architecture to do it without hesitation! I can't accurately express how beautiful Chicago is, which was actually surprising to me. It's absolutely stunning!! This was my 1st trip with Road Scholar & I'm inspired to travel with them again because everything about the trip was perfect! The hotel was beautiful & ccomfortable. Its location was spot on. The shared meals were all delicious. Our tour guide was so personable that we all felt like she was a friend, who cared for each one of us. The field trips were amaazing & the instructors so knowledgable & excited about sharing their beautiful city with us. I know that I was not the only one in the group of 22 that really didn't want to leave.
— Review left October 27, 2023
OUR TOUR THROUGH THE WINDY CITY WAS FUN AND INFORMATIVE. THE DIRECTOR AND INSTRUCTORS GAVE US A WEATH OF INFORMATION ABOUT THE ART AND ARCHITECTURE THAT OPENED MY EYES!
— Review left September 11, 2023
This trip to Chicago was a total winner! The city is clean, safe and full of amazing architecture, art and beautiful gardens along every street.
— Review left September 9, 2023
If you haven’t been to Chicago you are in for a treat. It’s a vibrant, lively, friendly
up to date and very clean city’s with a lot of interesting architecture and locations to explore
— Review left September 9, 2023
This trip is a fabulous intro to the architecture throughout and nearby Chicago. So many styles and buildings to see, including the details of art deco lobbies, atriums, window designs. Plenty of walking periods, so be ready for that. Quite a lot of learning packed into effectively 4 touring days. You might want to plan an extra day or two to see more on your own, and I highly recommend the Chicago History Museum north of downtown.(an easy Uber or Lyft ride) The Holy Name Cathedral was a pleasant surprise -- beautiful arts & crafts-like interior wood and glass inside a more conventional stone exterior. Beware the heavy carbs in all the group meals at Italian restaurants.
— Review left July 3, 2023
Interesting. Fun. Entertains.
— Review left June 29, 2023
Chicago Art & Architecture is an interesting and stimulating trip. The walks around the city and the places we went completely contradict the many negative stereotypes about Chicago that are embedded in a lot of popular culture. I met so many wonderful people on this trip who enriched the whole experience. The trip to Oak Park and the architecture boat trip are real highlights. I’d never been to Chicago before but I want to come back and visit more places. Our group leader Sue did a great job herding cats and helping everyone participate, always helpful and good-natured.
— Review left June 20, 2023
I have been telling friends and family how wonderful this program was.
— Review left June 18, 2023
Chicago is a great city. Beautiful place and spaces. Friendly people. Wonderful museums and interesting mix of old and new buildings and architecture. Well worth a trip.
— Review left June 17, 2023
This was a great introduction to Chicago! I learned a lot about the architecture of the city, and I am ready to visit again on my own!
— Review left May 24, 2023
This was our first Road Scholar program and it really delivered! A great overview of the city of Chicago. Our tour guides were excellent and we enjoyed meeting the other participants. Highly recommend!
— Review left May 16, 2023
Winding Your Way Through the Windy City is a fun and informative introduction to Chicago. If you are interested in great art, architecture, world class museums, a great aquarium, beautiful outdoor spaces, Millenium Park, the Bean, an architectural river cruise and Frank Lloyd Wright's work, or any of the above, this trip is for you. Great people and wonderful leader, and plenty of flexibility and free time!
— Review left May 16, 2023
Comprehensive tour of Chicago. Learned so much about the architecture of the late 1800's and early 1900's.
— Review left May 13, 2023
The skyline of Chicago has changed so much since my last visit. The program was a great learning experience. The tour to Oak Park was a highlight.
The Art Institute of Chicago is a treasure. The program allowed us to also spend
our free afternoon there. An hour is not enough.
— Review left September 25, 2022
This program delivered a fine balance between group learning and free time to explore Chicago on our own.
— Review left September 10, 2022
My husband and I had a wonderful time in Chicago. We really got to experience the downtown area and take advantage of many of the cultural sites: The Art Institute, Millennium Park, Theater, and exploring Michigan Avenue. Our guide was wonderful and our accommodations were in a great location.
— Review left July 23, 2022
Winding Through the Windy City is a Road Scholar experience not to be missed. Leader Susan Diamond and her team made sure we learned all that we could about the Art and Architecture in Chicago. They were flexible when the weather turned unseasonably Hot, changing the itinerary to make the educational experience even better, but more comfortable and safe for us. I learned that Chicago is a fascinating and approachable city. I highly recommend this program.
— Review left June 17, 2022
We’ve been on quite a few Road Scholar trips. This was our first visit to Chicago, and it was a good introduction to a great city. There was a nice balance of planned activities and tours and free time. Our trip leader, Sue, really made the week special. She was extremely helpful in suggesting things to do during free time. She also invited anyone interested to explore with her. Sue helped me find a relative’s former home in Oak Park during our visit there. It wasn’t part of our tour, but she made it happen. We enjoyed the city, the food, the other participants, and even the rainy days!
— Review left November 11, 2021
Chicago is an amazing city. It is very walkable and there are so many things to see and do within the downtown area. I would love to come back and see more.
— Review left October 30, 2021
The care and thought that goes into planning a trip is enormous. When you sign up with Road Scholar, all of the research and organization is done by someone else. All of the guesswork is off your plate. It is so easy to show up and then be taken to wonderful, breathtaking places and the best food! No worries, no delays, no buying tickets, no cooking or cleaning; only living life to its fullest.
Lonnie was very kind and personable. She answered all our questions easily.
Joe was a wonderful tour guide. I loved his immense knowledge and corny jokes. Upon meeting him, he felt like a friend you’ve always had.
Kenny the bus driver we had both days was miraculous. From the tiny streets he got that huge bus down to the last-minute driving directions he was given, he drove safely. Feeling comfortable when being driven is important.
Lastly, the whole concept of the program being Art & Architecture is amazing. I’ve never found a company that offers my specific interests in a city tour!
— Review left September 27, 2021
This was my first trip with RS. The planning, leaders, and places we were taken were absolutely superior!! I had never been to Chicago- i fell in love with it. The leaders were amazing. Took care of everything!! , .
— Review left December 2, 2019
The program exceeded our expectations. The leaders were excellent and warm. The lectures informative and our fellow RoadScholars were delightful. We found out that Chicago is our kind of town!
— Review left September 25, 2019
If you are hesitant about traveling solo, try Road Scholar. I was, I did and am glad for it.
MH, first time RS traveler but not the last.
— Review left July 23, 2019
Wonderful introduction or return visit to Chicago.
— Review left June 29, 2019
This program was great. The flex time was wonderful, allowing me to absorb some new information and explore things I was particularly interested in. Leaders were wonderful.
— Review left June 22, 2019
We were disapointed Elderhostel participants years ago and now are pleased with the creation of the Road Scholar off-shoot and the programs available for participants of all ages.
— Review left June 22, 2019
Great value and soooo educational.
— Review left June 21, 2019