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21908
Illinois

Winding Through the Windy City: Art & Architecture in Chicago

On expert-led, small group walks and during independent explorations, learn about Chicago’s historic architecture and diverse neighborhoods with local experts.
Rating (5)
Program No. 21908RJ
Length
6 days
Starts at
1,679
Illinois

Winding Through the Windy City: Art & Architecture in Chicago

On expert-led, small group walks and during independent explorations, learn about Chicago’s historic architecture and diverse neighborhoods with local experts.
Length
6 days
Starts at
1,679
Program No. 21908 RJ
Prefer to enroll or inquire by phone? 800-454-5768
climate
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Prices displayed below are based on per person,doubleoccupancy.
DATES & starting prices
PRICES
Oct 24 - Oct 29, 2021
Starting at
1,679
May 15 - May 20, 2022
Starting at
1,699
Jun 12 - Jun 17, 2022
Starting at
1,699
Jul 17 - Jul 22, 2022
Starting at
1,699
Aug 7 - Aug 12, 2022
Starting at
1,699
Sep 4 - Sep 9, 2022
Starting at
1,699
Oct 16 - Oct 21, 2022
Starting at
1,699
DATES & starting prices
PRICES
Oct 24 - Oct 29, 2021
Starting at
2,119
May 15 - May 20, 2022
Starting at
2,119
Jun 12 - Jun 17, 2022
Starting at
2,119
Jul 17 - Jul 22, 2022
Starting at
2,119
Aug 7 - Aug 12, 2022
Starting at
2,119
Sep 4 - Sep 9, 2022
Starting at
2,119
Oct 16 - Oct 21, 2022
Starting at
2,119

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
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Marshall Jacobson
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.

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 Shoemaker
Sue Shoemaker View biography
Sue Shoemaker grew up in a suburban, middle-class community near Detroit in the 1960's, the daughter of a Ford Motor Company employee and a stay-at-home mom. She has fond memories of visiting Detroit as a child. Sue has worked as a leader at Greenfield Village, an 8th grade English teacher and middle school guidance counselor. A passion for travel, learning and teaching has lead Sue to her current role facilitating Underground Railroad programs in Detroit and Ontario and group leading across the Great Lakes.
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.
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.
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.
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.
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 of Chicago.
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. You’ll also gain valuable insight into groundbreaking Chicago events and major figures down through history, including: The Birth of a Major Trade City The Great Fire of 1871 Construction of the Sears Tower Chicago’s “Public Enemies” The University of Chicago ...and more.
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.
The Devil in the White City: Murder, Magic and Madness at the Fair that Changed America
by Erik Larson
Erik Larson intertwines the true tale of the 1893 World's Fair and the cunning serial killer who used the fair to lure his victims to their death. Combining meticulous research with nail-biting storytelling, Erik Larson has crafted a narrative with all the wonder of newly discovered history and the thrills of the best fiction.
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.
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.
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.
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.
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.
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 battlefield-weary, demoralized men marching in the rain during the German attack on Caporetto and the profound struggle between loyalty and desertion, this 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 Hemingway's craft and creative process and the evolution of one of the greatest novels of the twentieth century. Featuring Hemingway's own 1948 introduction to an illustrated reissue of the novel, a personal foreword by the author's son, Patrick Hemingway, and a new introduction by the author's grandson, Sean Hemingway, this edition of A Farewell to Arms is truly a celebration.
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 Willis Tower. The Water Tower and all the other architectural features that make Chicago great are also included.
Loving Frank
by Nancy Horan
I have been standing on the side of life, watching it float by. I want to swim in the river. I want to feel the current. So writes Mamah Borthwick Cheney in her diary as she struggles to justify her clandestine love affair with Frank Lloyd Wright. Four years earlier, in 1903, Mamah and her husband, Edwin, had commissioned the renowned architect to design a new home for them. During the construction of the house, a powerful attraction developed between Mamah and Frank, and in time the lovers, each married with children, embarked on a course that would shock Chicago society and forever change their lives. In this ambitious debut novel, fact and fiction blend together brilliantly. While scholars have largely relegated Mamah to a footnote in the life of America’s greatest architect, author Nancy Horan gives full weight to their dramatic love story and illuminates Cheney’s profound influence on Wright. Drawing on years of research, Horan weaves little-known facts into a compelling narrative, vividly portraying the conflicts and struggles of a woman forced to choose between the roles of mother, wife, lover, and intellectual. Horan’s Mamah is a woman seeking to find her own place, her own creative calling in the world. Mamah’s is an unforgettable journey marked by choices that reshape her notions of love and responsibility, leading inexorably to this novel’s stunning conclusion.
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6 days
5 nights
10 meals
5 B 2 L 3 D
DAY
1
Check-in, Registration, Orientation, Welcome Dinner
Chicago, Illinois
D
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
Millennium Park & Art Institute, Free Time
Chicago, Illinois
B,D
Hyatt Place Chicago River North

Activity note: Walking approximately approximately 2 miles to/from Millennium Park, walking and standing up to 1 hour at museum.

Breakfast: At the hotel, we will enjoy a breakfast buffet, with coffee, tea, water included.

Morning: This morning we will visit Millennium Park, recipient of the 2009 Rudy Bruner Award for Urban Excellence. Here we will learn from an expert how this world-class public park was transformed from an industrial wasteland. In Chicago's most recent "jewel" on the lakefront, we will walk through the park and learn about its history, landscape, and fabulous sculptures, stopping for pictures at the renowned Cloud Gate, known popularly as The Bean. We will then walk across the street to the Art Institute to be led by an expert through its world-famous, permanent collection, housing 300,000 works of art.

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: 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.

Evening: At leisure.

DAY
3
City Field Trip by Motorcoach, Free Evening
Chicago, Illinois
B
Hyatt Place Chicago River North

Activity note: Getting on/off motorcoach. 4 hour exploration of the city by motorcoach with stops along the way.

Breakfast: Hotel buffet.

Morning: 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 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: On your own

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
Lecture on Architecture, Loop, Architectural Study Cruise
Chicago, Illinois
B,L
Hyatt Place Chicago River North

Activity note: Getting on/off boat. Walking approximately 2 miles on sidewalks in the city.

Breakfast: Hotel buffet.

Morning: We will explore the interior architecture of some of the Loop's most interesting architectural spaces, on foot. Themes we will explore this morning include the history and culture of Chicago, modernist architecture, infrastructure and design psychology.

Lunch: At a restaurant within walking distance to the river cruise boat dock, we will enjoy a plated lunch, plus coffee, tea, water; other beverages available for purchase.

Afternoon: We will then walk 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.

Dinner: On your own

Evening: At leisure.

DAY
5
Frank Lloyd Wright Home & Studio, Oak Park, Free Time
Chicago, Illinois
B,L,D
Hyatt Place Chicago River North

Activity note: Getting on/off motorcoach. 1 hour motorcoach exploration of historic Oak Park. 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, with a choice of main course, and coffee, tea (hot/iced), water included.

Afternoon: Free time.

Dinner: At a neighborhood restaurant, we will enjoy a tasty farewell dinner.

Evening: At leisure.

DAY
6
Program Concludes
Chicago, Illinois
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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