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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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 5 - May 10, 2024
Starting at
1,899
May 12 - May 17, 2024
Starting at
1,899
Filling Fast!
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
1,999
Sep 15 - Sep 20, 2024
Starting at
1,899
Itinerary Note

Private Group - OLLI-Cincinnati and ILR-Miami University

Filling Fast!
Oct 13 - Oct 18, 2024
Starting at
1,999
Full Inventory
Jun 29 - Jul 4, 2025
Starting at
1,999
Full Inventory
Jul 6 - Jul 11, 2025
Starting at
1,999
Full Inventory
Aug 3 - Aug 8, 2025
Starting at
1,999
Full Inventory
Sep 14 - Sep 19, 2025
Starting at
1,999
Full Inventory
Sep 21 - Sep 26, 2025
Starting at
1,999
DATES & starting prices
PRICES
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
Filling Fast!
Jul 14 - Jul 19, 2024
Starting at
2,319
Aug 4 - Aug 9, 2024
Starting at
2,319
Filling Fast!
Sep 1 - Sep 6, 2024
Starting at
2,419
Filling Fast!
Sep 15 - Sep 20, 2024
Starting at
2,319
Itinerary Note

Private Group - OLLI-Cincinnati and ILR-Miami University

Oct 13 - Oct 18, 2024
Starting at
2,419
Full Inventory
Jun 29 - Jul 4, 2025
Starting at
2,499
Full Inventory
Jul 6 - Jul 11, 2025
Starting at
2,499
Full Inventory
Aug 3 - Aug 8, 2025
Starting at
2,499
Full Inventory
Sep 14 - Sep 19, 2025
Starting at
2,499
Full Inventory
Sep 21 - Sep 26, 2025
Starting at
2,499

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.

What You'll Learn

  • 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 trip experts
Profile Image
Joe Cunniff
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.

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 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.
Profile Image of Mandy Golec
Mandy Golec View biography
Mandy Golec 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 out of 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 Phyliss Kozlowski
Phyliss Kozlowski View biography
Dr. Phyllis Kozlowski is a native Chicagoan who has an extensive background in the history and architecture of the city. She has worked as a travel expert for several organizations giving tours locally and internationally. As a former college professor and author, she also has a background in art history. She has often been invited to give lectures on the city and its cultural scene. Recognized as an outstanding educator, her enthusiasm for sharing information about her city is evident in all her presentations.
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