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!

Enroll with Confidence

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

Prefer to enroll or inquire by phone? 800-454-5768
Select your type of room
Price will update based on selection
Prices displayed below are based on per person,doubleoccupancy.
DATES & starting prices
PRICES
May 9 - May 14, 2024
Starting at
1,849
Filling Fast!
May 23 - May 28, 2024
Starting at
1,849
Filling Fast!
Jun 13 - Jun 18, 2024
Starting at
1,849
Jul 25 - Jul 30, 2024
Starting at
1,849
Filling Fast!
Sep 5 - Sep 10, 2024
Starting at
1,849
Oct 10 - Oct 15, 2024
Starting at
1,849
Full Inventory
May 4 - May 9, 2025
Starting at
2,349
May 11 - May 16, 2025
Starting at
2,349
Full Inventory
Jun 8 - Jun 13, 2025
Starting at
2,349
Full Inventory
Jul 13 - Jul 18, 2025
Starting at
2,349
Full Inventory
Aug 10 - Aug 15, 2025
Starting at
2,349
Full Inventory
Sep 14 - Sep 19, 2025
Starting at
2,349
Full Inventory
Sep 28 - Oct 3, 2025
Starting at
2,349
Full Inventory
Oct 5 - Oct 10, 2025
Starting at
2,349
DATES & starting prices
PRICES
May 9 - May 14, 2024
Starting at
2,269
Filling Fast!
May 23 - May 28, 2024
Starting at
2,269
Filling Fast!
Jun 13 - Jun 18, 2024
Starting at
2,269
Jul 25 - Jul 30, 2024
Starting at
2,269
Sep 5 - Sep 10, 2024
Starting at
2,269
Oct 10 - Oct 15, 2024
Starting at
2,269
Full Inventory
May 4 - May 9, 2025
Starting at
2,799
Filling Fast!
May 11 - May 16, 2025
Starting at
2,799
Full Inventory
Jun 8 - Jun 13, 2025
Starting at
2,799
Full Inventory
Jul 13 - Jul 18, 2025
Starting at
2,799
Full Inventory
Aug 10 - Aug 15, 2025
Starting at
2,799
Full Inventory
Sep 14 - Sep 19, 2025
Starting at
2,799
Full Inventory
Sep 28 - Oct 3, 2025
Starting at
2,799
Full Inventory
Oct 5 - Oct 10, 2025
Starting at
2,799

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 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 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.





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