Illinois
Winding Through the Windy City: Art & Architecture in Chicago
Program No. 2190860MEADV-1116-60
On expert-led, small group walks and during independent explorations, learn about Chicago’s historic architecture and diverse neighborhoods with local experts.
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800-454-5768
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DATES
& starting prices
PRICES
May 11 - May 16, 2025
Starting at
1,999DATES
& starting prices
PRICES
May 11 - May 16, 2025
Starting at
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This date is available to book as a private experience for your group!
6 days
5 nights
11 meals
5B 3L 3D
4
Architectural Study Cruise, Free Time
Chicago, IL
6
Program Concludes
Chicago, IL
At a Glance
Thrilling and serene. Tough and sophisticated. Chicago is a city of contrasts best understood through its art and architecture. We’ll be on the go with a small group of fellow explorers as we visit a range of neighborhoods with an architecture expert to see how the city’s evolution is told through its buildings. Then we’ll venture outside the city to learn about the life and work of Frank Lloyd Wright, as we visit his Prairie-style home and studio. Your schedule includes some open afternoons, during which you’ll be able to discover on your own the aspects of the city that speak to you most.
Activity Level
Keep the Pace
Walking up to two miles on field trips.
Small Group
Love to learn and explore in a small-group setting? These adventures offer small, personal experiences with groups of 13 to 24 participants.
Best of all, you’ll…
- Go inside the Art Institute of Chicago with an expert on the artworks of its world-class, 300,000-piece permanent collection.
- Study city architecture on a walk with a scholar and from a boat on the Chicago River.
- Learn about the life and work of the iconic architect Frank Lloyd Wright, through an expert-led exploration of his Prairie-style home and studio in charming and historic Oak Park, Illinois.
General Notes
Program includes independent time to explore the city. Group Leaders will provide directions for self-directed excursions. Suggestions for free-time activities provided in preparatory materials. You may enjoy a more inclusive, easier-paced "Signature City Chicago" (#2818).
Featured Expert
All trip experts
Joe Cunniff
Joseph Cuniff writes about the theater and music scene in Chicago, and is an instructor at the School of New Learning at DePaul University. He has led classes at the Art Institute of Chicago for more than 10 years. He earned a master’s in fine arts and interdisciplinary learning from Loyola University.
Please note: This expert may not be available for every date of this program.
Joe Cunniff
View biography
Joseph Cuniff writes about the theater and music scene in Chicago, and is an instructor at the School of New Learning at DePaul University. He has led classes at the Art Institute of Chicago for more than 10 years. He earned a master’s in fine arts and interdisciplinary learning from Loyola University.
Mandy Piotrowski
View biography
Mandy Piotrowski is a Chicago native with a passion for history, both mundane and bizarre. Having grown up in the city, she now splits her time between Chicago and Milwaukee, primarily doing museum and local walking expeditions. She is certified in D.C. and New York City, is a certified International Tour Manager through the International Guide Academy in Denver, and has written a variety of walking programs for Chicago, ranging from art history to women's history to city history.
Suggested Reading List
(15 books)
Visit the Road Scholar Bookshop
You can find many of the books we recommend at the Road Scholar store on bookshop.org, a website that supports local bookstores.
Winding Through the Windy City: Art & Architecture in Chicago
Program Number: 21908
Boss: Richard J. Daley of Chicago
This is the story of the late Richard J. Daley, politician and self-promoter extraordinaire, from his inauspicious youth on Chicago’s South Side through his rapid climb to the seat of power as mayor and boss of the Democratic Party machine. A bare-all account of Daley’s cardinal sins as well as his milestone achievements, this scathing work by Chicago journalist Mike Royko brings to life the most powerful political figure of his time: his laissez-faire policy toward corruption, his unique brand of public relations, and the widespread influence that earned him the epithet of “king maker.” The politician, the machine, the city—Royko reveals all with witty insight and unwavering honesty, in this incredible portrait of the last of the backroom Caesars. This new edition includes an Introduction in which the author reflects on Daley’s death and the future of Chicago.
Capone: The Life and World of Al Capone
The public called him Scarface; the FBI called him Public Enemy Number One; his associates called him Snorky. But Capone is the name most remember. And John Kobler’s Capone is the definitive biography of this most brutal and flamboyant of the underground kings—an intimate and dramatic book that presents a complete view of Al Capone and his gaudy era. Here is Capone’s story: his violent childhood in Brooklyn, his lieutenancy to Johnny Torrio, his rise in the ranks of the underworld, the notorious St. Valentine Massacre, his eventual control of the entire city of Chicago, and his decline during his imprisonment in Alcatraz. Capone was the ultimate gangster, and Capone is the ultimate in gangster biographies—a classic in the literature of crime.
Chicago: A Brief History
"Chicago: A Brief History" presents a comprehensive look at the city’s transformation from a fur trade outpost to America’s Second City. This compact digital compendium helps you track the diverse forces that shaped the city as we know it. You’ll explore the exciting history behind the city’s cultural, economic, and architectural mainstays.
Death at the Fair
The 1893 World's Columbian Exposition provides a vibrant backdrop for this exciting new mystery. Emily Cabot is one of the first women graduate students at the University of Chicago, eager to prove herself in the new field of sociology. While she is busy exploring the Exposition with her family and friends, her colleague, Dr. Stephen Chapman, is accused of murder. Emily sets out to search for the truth behind the crime, but is thwarted by the thieves, corrupt politicians, and gamblers who are ever-present in Chicago. A lynching that occurred in the dead man's past leads Emily to seek the assistance of the black activist Ida B. Wells. Rich with historical details that bring turn-of-the-century Chicago to life, this novel will appeal equally to history buffs and mystery fans.
Chicago Days: 150 Defining Moments in the Life of a Great City
Journey back through time to relive events that shaped the Chicago metropolitan area and contributed to its world-class reputation. Chicago Days is a collection of 150 essays and 500 dramatic photographs compiled from the voluminous files of the Chicago Tribune, the Chicago Historical Society, and other important collections.
Presumed Innocent
"Hailed as the most suspenseful and compelling novel in decades, PRESUMED INNOCENT brings to life our worst nightmare: that of an ordinary citizen facing conviction for the most terrible of all crimes. It's the stunning portrayal of one man's all-too-human, all-consuming fatal attraction for a passionate woman who is not his wife, and the story of how his obsession puts everything he loves and values on trial--including his own life. It's a book that lays bare a shocking world of betrayal and murder, as well as the hidden depths of the human heart. And it will hold you and haunt you...long after you have reached its shattering conclusion.
Biography
Scott Turow was born in Chicago in 1949. He graduated with high honors from Amherst College in 1970, receiving a fellowship to Stanford University Creative Writing Center which he attended from 1970 to 1972. From 1972 to 1975 Turow taught creative writing at Stanford. In 1975, he entered Harvard Law School, graduating with honors in 1978. From 1978 to 1986, he was an Assistant United States Attorney in Chicago, serving as lead prosecutor in several high-visibility federal trials investigating corruption in the Illinois judiciary. In 1995, in a major pro bono legal effort he won a reversal in the murder conviction of a man who had spent 11 years in prison, many of them on death row, for a crime another man confessed to.
Today, Scott Turow is a partner in the Chicago office of Sonnenschein, Nath & Rosenthal an international law firm, where his practice centers on white-collar criminal litigation and involves representation of individuals and companies in all phases of criminal matters. Turow lives outside Chicago"
Chicago Then and Now
The latest installment in the popular Then and Now series showcases the capital of the Heartland and one of the premier cities in the nation and the world: Chicago. Chicago's change and growth over the last century is captured in this photographic history. Modern color photos sit side by side with black and white archival photographs. Every important building, avenue, neighborhood, and point of interest is documented. It covers all of Chicago's landmarks from Navy Pier to the Stockyards and from the Southside all the way up the Magnificent Mile. Take in a game at Wrigley Field, then take it all in from the top of the Sear's Tower. The Water Tower and all the other architectural features that make Chicago great are also included.
Return to the Scene of the Crime: A Guide to Infamous Places in Chicago
This is an uncensored neighborhood-by-neighborhood map to the back alleys and boulevards of Chicago where some of the most infamous events of the city's criminal past occurred. Capone, Dillinger, and other organized crime figures have left an indelible imprint on the Windy City.
The Chicago River: A Natural and Unnatural History
An Intimate Biography of the Heroic Creek that Chicago Made. When French explorers Jolliet and Marquette used the Chicago portage to access the Mississippi River system, the Chicago River was but a humble, even sluggish, stream in the right place at the right time. That's the story of the making of Chicago. This is the other story--the story of the making and perpetual re-making of a river by everything from pre-glacial forces to the interventions of an emerging and mighty city.
The Old Man & The Sea
It is the story of an epic struggle between an old, seasoned fisherman and the greatest catch of his life. For eighty-four days, Santiago, an aged Cuban fisherman, has set out to sea and returned empty-handed. So conspicuously unlucky is he that the parents of his young devoted apprentice and friend, Manolin, have forced the boy to leave the old man in order to fish in a more prosperous boat. nevertheless, the boy continues to care for the old man upon his return each night. He helps the old man tote his gear to his ramshackle hut, secures food for him, and discusses the latest developments in American baseball, especially the trials of the old man's hero, Joe Dimaggio. Santiago is confident that his unproductive streak will soon come to an end, and he resolves to sail out farther than usual the following day.
Chicago Blues: The City & the Music
Chicago has always had a reputation as a ”wide open town” with a high tolerance for gangsters, illegal liquor, and crooked politicians. It has also been the home for countless black musicians and the birthplace of a distinctly urban blues—more sophisticated, cynical, and street-smart than the anguished songs of the Mississippi delta—a music called the Chicago blues. This is the history of that music and the dozens of black artists who congregated on the South and Near West Sides. Muddy Waters, Big Bill Broonzy, Howlin’ Wolf, Elmore James, Tampa Red, Little Walter, Jimmy Reed, Otis Rush, Sonny Boy Williamson, Junior Wells, Eddie Taylor—all of these giants played throughout the city and created a musical style that had imitators and influence all over the world.
The Devil in the White City, Murder, Magic, and Madness at the Fair That Changed America
This fascinating account of Chicago's 1893 World's Fair interweaves the true stories of Daniel H. Burnham, the architect responsible for the fair's construction, and H.H. Holmes, a serial killer masquerading as a charming doctor, who terrorized its visitors.
A Farewell To Arms
Written when Ernest Hemingway was thirty years old and lauded as the best American novel to emerge from World War I, A Farewell to Arms is the unforgettable story of an American ambulance driver on the Italian front and his passion for a beautiful English nurse. Set against the looming horrors of the battlefieldweary, demoralized men marching in the rain during the German attack on Caporetto; the profound struggle between loyalty and desertionthis gripping, semi autobiographical work captures the harsh realities of war and the pain of lovers caught in its inexorable sweep.
Ernest Hemingway famously said that he rewrote the ending to A Farewell to Arms thirty-nine times to get the words right. This edition collects all of the alternative endings together for the first time, along with early drafts of other essential passages, offering new insight into Hemingways craft and creative process and the evolution of one of the greatest novels of the twentieth century. Featuring Hemingways own 1948 introduction to an illustrated reissue of the novel, a personal foreword by the authors son Patrick Hemingway, and a new introduction by the authors grandson Sen Hemingway, this edition of A Farewell to Arms is truly a celebration.
Loving Frank
Fact and fiction blend in a historical novel that chronicles the relationship between Frank Lloyd Wright and Mamah Cheney, from their meeting in Oak Park, when they were each married to another, to the clandestine affair that shocked Chicago society.
Lost Chicago
"The City of Big Shoulders has always been our most quintessentially American—and world-class—architectural metropolis. In the wake of the Great Fire of 1871, a great building boom—still the largest in the history of the nation—introduced the first modern skyscrapers to the Chicago skyline and began what would become a legacy of diverse, influential, and iconoclastic contributions to the city’s built environment. Though this trend continued well into the twentieth century, sour city finances and unnecessary acts of demolishment left many previous cultural attractions abandoned and then destroyed.
Lost Chicago explores the architectural and cultural history of this great American city, a city whose architectural heritage was recklessly squandered during the second half of the twentieth century. David Garrard Lowe’s crisp, lively prose and over 270 rare photographs and prints, illuminate the decades when Gustavus Swift and Philip D. Armour ruled the greatest stockyards in the world; when industrialists and entrepreneurs such as Cyrus McCormick, Potter Palmer, George Pullman, and Marshall Field made Prairie Avenue and State Street the rivals of New York City’s Fifth Avenue; and when Louis Sullivan, Daniel Burnham, and Frank Lloyd Wright were designing buildings of incomparable excellence. Here are the mansions and grand hotels, the office buildings that met technical perfection (including the first skyscraper), and the stores, trains, movie palaces, parks, and racetracks that thrilled residents and tourists alike before falling victim to the wrecking ball of progress."
Program
At a Glance
Duration
6 days
Program Begins
Chicago, IL
Program Concludes
Chicago, IL
Group Type
Small Group
Meals
11
| 5B |
3L |
3D |
Activity Level
Thrilling and serene. Tough and sophisticated. Chicago is a city of contrasts best understood through its art and architecture. We’ll be on the go with a small group of fellow explorers as we visit a range of neighborhoods with an architecture expert to see how the city’s evolution is told through its buildings. Then we’ll venture outside the city to learn about the life and work of Frank Lloyd Wright, as we visit his Prairie-style home and studio. Your schedule includes some open afternoons, during which you’ll be able to discover on your own the aspects of the city that speak to you most.)
Best of all, you'll...
- Go inside the Art Institute of Chicago with an expert on the artworks of its world-class, 300,000-piece permanent collection.
- Study city architecture on a walk with a scholar and from a boat on the Chicago River.
- Learn about the life and work of the iconic architect Frank Lloyd Wright, through an expert-led exploration of his Prairie-style home and studio in charming and historic Oak Park, Illinois.
General Notes
Program includes independent time to explore the city. Group Leaders will provide directions for self-directed excursions. Suggestions for free-time activities provided in preparatory materials. You may enjoy a more inclusive, easier-paced "Signature City Chicago" (#2818).
Featured Expert
Joe Cunniff
Joseph Cuniff writes about the theater and music scene in Chicago, and is an instructor at the School of New Learning at DePaul University. He has led classes at the Art Institute of Chicago for more than 10 years. He earned a master’s in fine arts and interdisciplinary learning from Loyola University.
Please Note:
This expert may not be available for every date of the program
Activity Level
Keep the Pace
Walking up to two miles on field trips.
Small Group
(13 to 24)
Love to learn and explore in a small-group setting? These adventures offer small, personal experiences with groups of 13 to 24 participants.
Suggested Reading List
View Full List
(15 Books)
You can also find many of the books we recommend at the Road Scholar store on bookshop.org, a website that supports local bookstores.
HAVE QUESTIONS?
Prefer to enroll or inquire by phone?
We can help. Give us a call, and we can answer all of your questions!
Call
800-454-5768
While we make every effort to ensure the accuracy of our published materials, programs are typically advertised more than a year prior to their start date. As a result, some program activities, schedules, accommodations, personnel, and other logistics occasionally change due to local conditions or circumstances. Should a major change occur, we will make every effort to alert you. For less significant changes, we will update you during orientation. Thank you for your understanding.
Duration
6 days
5 nights
What's Included
11 meals | 5B | 3L | 3D |
2 expert-led lectures
6 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Day
1
Check-in, Registration, Orientation, Welcome Dinner
Location:
Chicago, IL
Meals:
D
Stay:
Hyatt Place Chicago River North
Activity Note
Hotel check-in from 3:00 p.m.
Afternoon:
Program Registration, 3:00 p.m. - 5:00 pm. After you have your room assignment, come over to the Road Scholar table in the hotel lobby to register with the program staff.
Dinner:
We will have dinner out at a neighborhood restaurant within walking distance of the hotel.
Evening:
Orientation: The Group Leader will greet everyone and lead introductions. We will review the up-to-date program schedule, discuss roles and responsibilities, logistics, safety guidelines, emergency procedures, and answer questions. Periods in the daily schedule designated as “Free time” and “At leisure” offer opportunities to do what you like and make your experience even more meaningful and memorable according to your personal preferences. The Group Leader will be happy to offer suggestions. Program activities, schedules, personnel, and indicated distances or times may change due to local circumstances/conditions. In the event of changes, we will alert you as quickly as possible. Thank you for your understanding. The remainder of the evening is free to continue getting to know your fellow participants. Settle in to your room and get a good night’s sleep for the full day tomorrow.
Day
2
Chicago History Lecture, Art Institute, Free Time.
Location:
Chicago, IL
Meals:
B,D
Stay:
Hyatt Place Chicago River North
Activity Note
Walking up to 2 miles and standing up to 1 hour in the Art Institute.
Breakfast:
At the hotel, we will enjoy a breakfast buffet, with coffee, tea, water included.
Morning:
At the hotel, we will begin our explorations with an expert-led lecture on the history of the Chicago area from the early indigenous people through the Great Migration, noting current trends and dynamics in this fascinating city. We will then go on an expert-led exploration of the world-famous Art Institute of Chicago, where we will hone our knowledge of and appreciation for art. Highlights of the permanent collection – comprising more than 300,000 works in different media – include “American Gothic,” the famed Chagall Windows, and the Thorne Miniature Rooms. Led by an art educator, we will have an introduction to key galleries, followed by self-led exploration to explore the museum in greater depth.
Lunch:
This meal has been excluded from the program cost and is on your own to enjoy what you like. The Group Leader will be happy to offer suggestions.
Afternoon:
After lunch we continue to independently explore the extensive collections at the Art Institute of Chicago. In late afternoon our local expert will take us to Planetarium Point via coach to enjoy the magnificent skyline view of Chicago from across Lake Michigan. We then make our way back to the hotel on the coach.
Dinner:
At a neighborhood restaurant.
Evening:
At leisure.
Day
3
Art & Culture Lecture, City Coach Explorations, Free Time
Location:
Chicago, IL
Meals:
B,L
Stay:
Hyatt Place Chicago River North
Activity Note
Getting on/off motorcoach. 6 hour exploration of the city by motorcoach with stops along the way.
Breakfast:
Hotel buffet.
Morning:
We begin our day with a lecture focusing on the art and architecture in the Windy City by a local expert guide. Mark Twain wrote in 1883, “It is hopeless for the occasional visitor to try to keep up with Chicago. She outgrows his prophecies faster than he can make them.” Led by an expert, we will have a motorcoach exploration to learn more about Chicago history, the immigrants and neighborhoods who gave it a rich culture and texture, and the movers and shakers whose influence made it a world-class city. We’ll begin our journey north along Michigan Avenue to Lake Shore Drive and up to Wrigley Field, home of the Chicago Cubs. As time and traffic allow, we will stop at various locations along the way.
Lunch:
At a favorite local restaurant.
Afternoon:
Free time. Take this opportunity for personal independent exploration to see and do what interests you most. The Group Leader will be happy to offer suggestions.
Dinner:
On your own
Evening:
At leisure.
Day
4
Architectural Study Cruise, Free Time
Location:
Chicago, IL
Meals:
B,L
Stay:
Hyatt Place Chicago River North
Activity Note
Getting on/off boat. Activity level is dependent on individual pursuits during free time.
Breakfast:
Hotel buffet.
Morning:
We begin our day riding the motorcoach to the dock to embark on our river cruise, which will present more of Chicago’s extraordinary architecture and related social history. None other than Frank Lloyd Wright said, "[modern architecture] all started here..." By necessity due to geographical limitations, Chicago’s business leaders had to look upwards to expand after the devastating Great Chicago Fire of 1871. Within less than a decade, new building techniques pushed the city’s skyline ever higher. Some of the world’s greatest architects, supported by visionary business leaders, built not just higher, but sleeker and more sophisticated. And it was not only skyscrapers that forged a unique identity. Debris from the great fire created the base of Grant Park. The Merchandise Mart, once the epicenter of high design and luxury goods, owned for half a century by the Kennedy family, is the world’s largest commercial building. Chicago also has more movable bridges than any city in the world including an engineering wonder, the Michigan Avenue Bridge, one of the city’s foremost thoroughfares. We will learn about all this and much more during our cruise with expert commentary.
Lunch:
At a local restaurant within walking distance to the river cruise boat dock.
Afternoon:
Free time. This period of time has been set aside for your personal independent exploration to see and do what interests you most. Please refer to the list of Free Time Suggestions in your preparatory materials. The Group Leader will be happy to offer suggestions. Dinner is on your own this evening. Chicago has a vibrant local food scene; please see the Restaurant Suggestions in your preparatory materials.
Dinner:
On your own
Evening:
At leisure.
Day
5
Frank Lloyd Wright Home & Studio, Oak Park, Free Time
Location:
Chicago, IL
Meals:
B,L,D
Stay:
Hyatt Place Chicago River North
Activity Note
Getting on/off motorcoach. Driving up to 15 miles to historic Oak Park. Walking up to 1 mile exploring this neighborhood. The Frank Lloyd Wright Home is not accessible to wheelchairs of any size as all entries to the Home have stairs. The Studio balcony is not accessible to wheelchairs. It is only accessible by a steep, narrow stairway.
Breakfast:
Hotel buffet.
Morning:
This morning, we will board a motorcoach for historic Oak Park, home to iconic architect Frank Lloyd Wright from 1889 until 1909. It is in Oak Park that Wright created his Prairie-style of architecture. We will have the opportunity to explore his Oak Park home and studio with an expert on the subject. Afterwards, enjoy a self-guided exploration of historic Oak Park and River Forest, where we will learn more about the work of Wright and his contemporaries in the field. Oak Park is a charming suburb of Chicago, renowned for its rich historic architectural styles, including the largest concentration of Frank Lloyd Wright homes and buildings.
Lunch:
We will have lunch at a popular restaurant in Oak Park.
Afternoon:
Free time. Take this opportunity for personal independent exploration to see and do what interests you most. The Group Leader will be happy to offer suggestions.
Dinner:
At a neighborhood restaurant, we will enjoy a tasty farewell dinner.
Evening:
At leisure.
Day
6
Program Concludes
Location:
Chicago, IL
Meals:
B
Activity Note
Hotel check-out by 12:00 Noon.
Breakfast:
Hotel buffet. This concludes our program.
Morning:
If you are returning home, safe travels. If you are staying on independently, have a wonderful time. If you are transferring to another Road Scholar program, detailed instructions are included in your Information Packet for that program. We hope you enjoy Road Scholar learning adventures and look forward to having you on another rewarding program in the future. Don’t forget to join our Facebook page and follow us on Instagram. Best wishes for all your journeys!
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MEALS
11 Meals
5 Breakfasts
3 Lunches
3 Dinners
LODGING
Lodgings may differ by date. Select a date to see the lodgings specific to that date.
Showing Lodging For:
- Jun 29, 2025 - Jul 04, 2025
- May 11, 2025 - May 16, 2025
- Jun 29, 2025 - Jul 04, 2025
- Jul 06, 2025 - Jul 11, 2025
- Aug 03, 2025 - Aug 08, 2025
- Sep 14, 2025 - Sep 19, 2025
- Sep 21, 2025 - Sep 26, 2025
Participant Reviews
Based on 34 Reviews
Sort By:
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
Fun way to explore Chicago from a convenient hotel base.
— Review left June 17, 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
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
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 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
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
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
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
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
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
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
Great value and soooo educational.
— Review left June 21, 2019