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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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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Year
2024
  • 2024
  • 2025
Date
Jul 14 - Jul 19
  • May 05 - May 10
  • May 12 - May 17
  • Jun 09 - Jun 14
  • Jul 14 - Jul 19
  • Aug 04 - Aug 09
  • Sep 01 - Sep 06
  • Sep 15 - Sep 20
  • Oct 13 - Oct 18
Please Note: The program differs on certain dates.
Please Note: The program differs on certain dates.
Select trip year and date
2024
  • 2024
  • 2025
Jul 14 - Jul 19
  • May 05 - May 10
  • May 12 - May 17
  • Jun 09 - Jun 14
  • Jul 14 - Jul 19
  • Aug 04 - Aug 09
  • Sep 01 - Sep 06
  • Sep 15 - Sep 20
  • Oct 13 - Oct 18
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
11 meals
5 B 3 L 3 D
DAY
1
Check-in, Registration, Orientation, Welcome Dinner
Chicago, IL
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
Chicago History Lecture & Art Institute, Free Time.
Chicago, IL
B,D
Hyatt Place Chicago River North

Activity note: Walking up to 2 miles and standing up to 1 hour in the Art Institute.

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

Morning: At the hotel, we will begin our explorations with an expert-led lecture on the history of the Chicago area from the early indigenous people through the Great Migration, noting current trends and dynamics in this fascinating city. We will then 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.

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: After lunch we continue to independently explore the extensive collections at the Art Institute of Chicago. In late afternoon our local expert will take us to Planetarium Point via coach to enjoy the magnificent skyline view of Chicago from across Lake Michigan. We then make our way back to the hotel on the coach.

Dinner: At a neighborhood restaurant.

Evening: At leisure.

DAY
3
City Field Trip by Motorcoach, Free Evening
Chicago, IL
B,L
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: We begin our day with a lecture focusing on the art and architecture in the Windy City by a local expert. 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 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. 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: At a favorite local restaurant.

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, IL
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 begin our day walking 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.

Lunch: At a local restaurant within walking distance to the river cruise boat dock.

Afternoon: DePaul Art Museum (DPAM) is a world-class museum located in the heart of Lincoln Park on DePaul University’s campus. DPAM's commitment to excellence, diversity, and social concerns in art make this an exciting and currently relevant field trip. We'll enjoy both the temporary exhibitions and the permanent collection of more than 4,000 objects with strengths in international modern and contemporary art. We'll also experience some of Chicago's most recent and environmentally conscious architecture in this Leadership in Energy and Environmental Design (LEED) certified building, built in 2011. The coach returns to the hotel mid-afternoon so we can enjoy the free afternoon at leisure.

Dinner: On your own

Evening: At leisure.

DAY
5
Frank Lloyd Wright Home & Studio, Oak Park, Free Time
Chicago, IL
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.

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, we will enjoy a tasty farewell dinner.

Evening: At leisure.

DAY
6
Program Concludes
Chicago, IL
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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