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Signature City Chicago

Program No. 2818RJ
We’ve packed the best of Chicago into five unforgettable days. Join world-class experts at renowned museums, historic parks, iconic skyscrapers and more!

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At a Glance

If you have always wanted to experience Chicago, but didn’t know where to start, you’ve come to the right place. This introduction to the “Windy City” is brimming with expert-led visits to Chicago’s gems. Discover glittering skyscrapers, fine dining, revitalized lakefront, a diverse cultural scene, celebrated museums and the tony Magnificent Mile on an exceptional adventure that draws back the curtain on Chicagoans and “their kind of town.”
Activity Level
On Your Feet
Walking up to three miles per day, getting on and off the coach multiple times per day.

What You'll Learn

  • Examine Chicago’s growth on a expert-led field trip through the city’s diverse neighborhoods.
  • Experience the city’s Millennium Park and visit the Field Museum.
  • Explore the Chicago River and learn how Chicago grew from a settlement into one of the world's largest cities.

General Notes

You may enjoy a program with more free time to explore Chicago on your own in the "Winding Through the Windy City: Art & Architecture in Chicago" (#21908).
Featured Expert
All trip experts
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Brian Murray
Brian Murray is a graphic artist and educator based in Chicago for over two decades. Combining his local experience with his passion for art history and community organizing, Brian leads thought-provoking explorations of the art forms that adorn the walls of the city and the various perceptions and historical contexts around them.

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

Profile Image of Aurora Cruz Nelson
Aurora Cruz Nelson View biography
Aurora Cruz Nelson is a seasoned world traveler and infinite life learner. She strives to ensure that others are positively impacted by their travel; her experience has given her a global perspective that she wants to share. She is motivated by her dedication to quality life for all. Aurora has held positions in education, nonprofits, and travel sectors. Her strengths include creativity, curiosity, and gratitude. Her favorite person is her teenage son, who she took on a six-country gap year.
Profile Image of Mandy Piotroski
Mandy Piotroski View biography
Mandy Piotroski 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 IGA in Denver, and has written a variety of walking programs for Chicago, ranging from art history to women's history to city history.
Profile Image of Brian Murray
Brian Murray View biography
Brian Murray is a graphic artist and educator based in Chicago for over two decades. Combining his local experience with his passion for art history and community organizing, Brian leads thought-provoking explorations of the art forms that adorn the walls of the city and the various perceptions and historical contexts around them.
Profile Image of Zbigniew Banas
Zbigniew Banas View biography
Zbigniew Banas has been a resident of Chicago since 1976. He is currently an instructor at Loyola University in the department of modern languages and literature. He is also a radio host and reporter with WPNA and WEUR. He received his B.A. from the University of Chicago and his M.S. from Brown University. He has been involved with Road Scholar for over 15 years.
Profile Image of Bernard Turner
Bernard Turner View biography
Bernard Turner is executive director of the Bronzeville-Black Metropolis National Heritage Area focused on preserving the history and culture of his community. Author of several books about Chicago and African American History, including A New View of Bronzeville and Tate and His Historic Dream, Bernard conducts citywide and neighborhood explorations and has volunteered at the Chicago History Museum since 2000. Bernard taught German and Spanish in the Chicago area for several years before beginning a career in educational publishing in sales, sales management, and marketing.
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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.
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6 days
5 nights
12 meals
5 B 4 L 3 D
Registration, Hotel Check-in, Orientation, Welcome Dinner
Chicago, Illinois
SpringHill Suites Chicago Downtown/River North

Activity note: Walk four blocks to dinner and back

Afternoon: Program Registration begins at 3:00 p.m in the hotel lobby. Please join us at the Road Scholar table to register with the program staff, get any updated information, and confirm the time and location of the Orientation session. Hotel check-in is at 4:00 p.m. If you arrive late, please locate your Group Leader and let them know you have arrived. 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. In addition to our experienced and knowledgeable Group Leader, we will learn from a series of local experts who will give lectures and lead field trips. Program-related travel and transfers will be via private motorcoach unless noted otherwise. Meals will feature local cuisine in a variety of settings. Periods in the 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.

Dinner: Dinner at a local restaurant

Evening: At leisure. Continue getting to know your fellow Road Scholars, settle in, and get a good night's rest for the day ahead.

Lecture, City Field Trip
Chicago, Illinois
SpringHill Suites Chicago Downtown/River North

Activity note: Getting on/off a motorcoach multiple times throughout the day; walking up to 3 miles; driving through the city, approximately 2.5 hours total riding time.

Breakfast: At the hotel.

Morning: At the hotel, we will have an expert-led lecture on the history of the Chicago area from the early indigenous people through the Great Migration. We will then board our motorcoach for a city field trip. 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 go on 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.

Lunch: At a popular local restaurant.

Afternoon: After lunch we will visit the DuSable Museum of African American History. Founded in 1961 by Dr. Margaret Burroughs and her husband, Charles, the DuSable is the oldest museum of African American history in the country. We will return to the hotel in the late afternoon.

Dinner: This meal has been excluded from the program cost and is on your own to have what you like. The Group Leader will be happy to offer suggestions.

Evening: At leisure.

Lecture, Wrigley Field, Millenium Park, Chicago History Msm.
Chicago, Illinois
SpringHill Suites Chicago Downtown/River North

Activity note: Getting on/off a motorcoach; driving 15 miles, about 75 minutes hours total riding time. Walking and standing at museum is dependent upon personal preference; up to two hours.

Breakfast: Breakfast at the hotel.

Morning: We will start the day with an expert presentation on the fascinating world of Chicago Politics. Then we will take the motorcoach to explore more of Chicago. We 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, including Millennium Park which won the Rudy Bruner Award for Urban Excellence.

Lunch: Lunch at the Chicago History Museum.

Afternoon: After lunch, we will go on an expert-led field trip at the Chicago History Museum. This institution houses 22 million historical artifacts and documents from Chicago and U.S. history, with an emphasis on these main areas: Living/Working/Governing in the Metropolitan Area, the Built Environment, and Individuals and Ideas. We will gain a better understanding of Chicago’s past, its present, and prospects for the future.

Dinner: On your own to enjoy local fare.

Evening: At leisure.

Architectural Boat Tour, Field Museum of Natural History
Chicago, Illinois
SpringHill Suites Chicago Downtown/River North

Activity note: Getting on/off a motorcoach. Walking 2 blocks to/from the boat. Getting on/off a boat; cruising approximately 1.5 hours. Walking and standing a minimum of 1 hour in the museum.

Breakfast: Breakfast at the hotel.

Morning: This morning we will enjoy an architectural boat cruise on the Chicago River. None other than Frank Lloyd Wright said, “It [modern architecture] all started here….” Our study cruise this afternoon presents more of Chicago’s extraordinary architecture and related social history. 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 one of the world’s largest commercial buildings. Chicago also has more moveable bridges than any city in the world including an engineering wonder, the Michigan Avenue Bridge, one of the city’s foremost thoroughfares. We’ll learn about all this and much more during this cruise with expert commentary. Afterwards, we will depart the dock for lunch at the Field Museum.

Lunch: Lunch at leisure at the Field Museum. Vouchers will be distributed.

Afternoon: The Field Museum of Natural History is widely regarded as one of the finest natural history museums on the world. It originated in 1893 as the Columbian Museum of Chicago. The name was later changed to honor the generosity of benefactor and department store founder Marshall Field, and to better reflect a focus on the natural sciences. During a self-directed exploration, we’ll learn about the museum’s work and collections. Please note: The Field Museum does not have docents except for school groups. Please use the supplied map to direct your independent exploration. You will have ample time to delve into exhibits that interest you. Among its collections, you can learn about gems, dinosaurs, mummies, Africa, the Pacific, the Ancient Americas, Native Voices, and much more. The lakefront campus is also home to the Adler Planetarium and the Shedd Aquarium, together regarded as among the finest of their kind in the world. The motorcoach will depart the Field Museum at 4:00 p.m. You are welcome to stay and continue exploring or you may return to the hotel for an afternoon and evening on your own. If you choose to remain at the museum, you will need to find transportation back to the hotel, at your expense.

Dinner: At a local restaurant.

Evening: At leisure.

Mural Exploration, Art Institute
Chicago, Illinois
SpringHill Suites Chicago Downtown/River North

Activity note: Getting on/off a motorcoach. Walking up to two miles on the Mural Exploration; Walking and standing a minimum of 1 hour at the Art Institute.

Breakfast: Breakfast at the hotel.

Morning: We are joined by a local expert as we visit the some of the extraordinary street art in Chicago. Along the way, we’ll learn unique details about Chicago’s history and discover uplifting elements about the artists and the city. This is an upbeat exploration that shares how artists have improved neighborhoods one mural at a time.

Lunch: At a local restaurant within a short drive of the Art Institute of Chicago.

Afternoon: After lunch, we will 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. Return to the hotel in late afternoon.

Dinner: At a neighborhood restaurant. Share favorite experiences and enjoy camaraderie with new Road Scholar friends during our farewell dinner.

Evening: At leisure. Prepare for check-out and departure in the morning.

Program Concludes After Breakfast
Chicago, Illinois

Breakfast: Breakfast at the hotel.

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 rewarding programs 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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