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Illinois

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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We want your Road Scholar learning adventure to be something to look forward to—not worry about. Learn more

Protecting the Environment

We offset a portion of the emissions created by your travel. Learn more

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
Profile Image
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 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 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.
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.
Meals
12 Meals
5 Breakfasts
4 Lunches
3 Dinners
The following choices may be available when requested in advance: Gluten Free, Vegetarian
Lodging
Lodgings may differ by date. Select a date to see the lodgings specific to that date.
Display
Jul 25, 2024 - Jul 30, 2024
  • Jul 25, 2024 - Jul 30, 2024
  • May 23, 2024 - May 28, 2024
  • Jun 13, 2024 - Jun 18, 2024
  • Jul 25, 2024 - Jul 30, 2024
  • Sep 05, 2024 - Sep 10, 2024
  • Oct 10, 2024 - Oct 15, 2024
  • May 04, 2025 - May 09, 2025
  • May 11, 2025 - May 16, 2025
  • Jun 08, 2025 - Jun 13, 2025
  • Jul 13, 2025 - Jul 18, 2025
  • Aug 10, 2025 - Aug 15, 2025
  • Sep 14, 2025 - Sep 19, 2025
  • Sep 28, 2025 - Oct 03, 2025
  • Oct 05, 2025 - Oct 10, 2025
5 nights
Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet





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