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Illinois

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908RJ
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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Prices displayed below are based on per person,doubleoccupancy.
DATES & starting prices
PRICES
May 7 - May 12, 2023
Starting at
1,749
May 14 - May 19, 2023
Starting at
1,749
Jun 11 - Jun 16, 2023
Starting at
1,749
Jun 25 - Jun 30, 2023
Starting at
1,749
Jul 16 - Jul 21, 2023
Starting at
1,749
Aug 6 - Aug 11, 2023
Starting at
1,749
Sep 3 - Sep 8, 2023
Starting at
1,749
Oct 15 - Oct 20, 2023
Starting at
1,749
May 5 - May 10, 2024
Starting at
1,899
May 12 - May 17, 2024
Starting at
1,899
Jun 9 - Jun 14, 2024
Starting at
1,899
Jul 14 - Jul 19, 2024
Starting at
1,899
Aug 4 - Aug 9, 2024
Starting at
1,899
Sep 1 - Sep 6, 2024
Starting at
1,899
Oct 13 - Oct 18, 2024
Starting at
1,899
DATES & starting prices
PRICES
May 7 - May 12, 2023
Starting at
2,169
May 14 - May 19, 2023
Starting at
2,169
Jun 11 - Jun 16, 2023
Starting at
2,169
Jun 25 - Jun 30, 2023
Starting at
2,169
Jul 16 - Jul 21, 2023
Starting at
2,169
Aug 6 - Aug 11, 2023
Starting at
2,169
Sep 3 - Sep 8, 2023
Starting at
2,169
Oct 15 - Oct 20, 2023
Starting at
2,169
May 5 - May 10, 2024
Starting at
2,319
May 12 - May 17, 2024
Starting at
2,319
Jun 9 - Jun 14, 2024
Starting at
2,319
Jul 14 - Jul 19, 2024
Starting at
2,319
Aug 4 - Aug 9, 2024
Starting at
2,319
Sep 1 - Sep 6, 2024
Starting at
2,319
Oct 13 - Oct 18, 2024
Starting at
2,319

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
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 Experts
Profile Image
Sue Diamond
Susan Diamond is a lifelong Chicagoan, and an inspirational writer and thought leader with an international following on social media and Beliefnet.com. Susan is an active member of the esteemed Chicago Council on Global Affairs, a nonpartisan forum for world leaders, policymakers, and experts. Susan sits on the Chicago board of One Acre Fund, a leading NGO solving the problem of extreme poverty and chronic hunger through agricultural microfinance. Her background also includes expertise in running three successful businesses and lecturing on Middle East policy.

Please note: This expert may not be available for every date of this program.

Profile Image of Marshall Jacobson
Marshall Jacobson View biography
Born and raised in Chicago, Marshall Jacobson knows the Windy City! He graduated from South Shore High School and earned a bachelor’s degree in American history from the University of Illinois-Urbana and a master’s degree in social service administration at the University of Chicago. He is a Chicago Greeter and was a volunteer for five years for the Chicago Architecture Foundation as an award-winning docent. Marshall served as the vice president for development at the Frank Lloyd Wright Preservation Trust, and is an active supporter and visitor to the Chicago History Museum, the Lincoln Park Zoo, the Art Institute of Chicago and the Chicago Symphony Orchestra. In addition, Marshall actively participates in a variety of liberal arts classes, with favorites in art history and film, at Northwestern University. Besides being a bon vivant and Renaissance man, Marshall is an actor and has performed in several productions around Chicago.
Profile Image of Sue Diamond
Sue Diamond View biography
Susan Diamond is a lifelong Chicagoan, and an inspirational writer and thought leader with an international following on social media and Beliefnet.com. Susan is an active member of the esteemed Chicago Council on Global Affairs, a nonpartisan forum for world leaders, policymakers, and experts. Susan sits on the Chicago board of One Acre Fund, a leading NGO solving the problem of extreme poverty and chronic hunger through agricultural microfinance. Her background also includes expertise in running three successful businesses and lecturing on Middle East policy.
Profile Image of Andrea Maremont
Andrea Maremont View biography
A native of northwest Indiana, Andrea Maremont has lived in the Windy City for nearly 50 years. She has been a group leader for Road Scholar for more than 10 years, and has helped to design learning adventures in the city. When not leading educational expeditions throughout Chicago, Andrea is the director of a small senior center.
Profile Image of Karen Kaplan
Karen Kaplan View biography
Karen Kaplan was born and raised in West Rogers Park on the North Side of Chicago. She graduated from the University of Illinois at Chicago and began her career as a nutritionist, speaking to audiences on health and wellness. After raising her family in the Chicago area, Karen wrote her memoir and began speaking internationally. Karen's love of The Windy City has led her to become a Road Scholar Group Leader who enjoys sharing her stories of Chicago.
Profile Image of Joe Cunniff
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.
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.
A Farewell To Arms
by Ernest Hemingway
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.
Chicago Days: 150 Defining Moments in the Life of a Great City
by Chicago Tribune
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.
Return to the Scene of the Crime: A Guide to Infamous Places in Chicago
by Richard Lindberg
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.
Presumed Innocent
by Scott Turow
"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
by Elizabeth McNulty
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.
Chicago Blues: The City & the Music
by Mike Rowe
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
by Erik Larson
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.
The Chicago River: A Natural and Unnatural History
by Libby Hill
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.
Death at the Fair
by Frances McNamara
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.
Boss: Richard J. Daley of Chicago
by Mike Royko
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
by John Kobler
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.
Loving Frank
by Nancy Horan
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.
The Old Man & The Sea
by Ernest Hemingway
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.
Lost Chicago
by David Garrard Lowe
"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."
Chicago: A Brief History
by Vook
"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.





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