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Illinois

Go Solo: Art and Architecture in Chicago

Program No. 24935RJ
Embark on an adventure with other solo travelers, learning 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,singleoccupancy.

DATES & PRICES

Single Lodging
Rooms, cabins or berths designated as single occupancy accommodations.
May 4 - May 9, 2025
Single Lodging 2,499
This date is available to book as a private experience for your group!

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 solo travelers 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 and why going solo with Road Scholar doesn’t mean going alone!
Activity Level
Keep the Pace
Walking up to five 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.

Best of all, you’ll…

  • Go inside the Art Institute of Chicago with an expert on the artworks of its world-class, 300,000-piece permanent collection.
  • 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.
  • Study city architecture on a walk with an expert and from a boat on the Chicago River, exploring the city with other solo explorers who love learning as much as you do.

General Notes

This program is exclusive to solo travelers attending the program without a travelling companion.
Featured Expert
All trip experts
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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 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 Piotrowski
Mandy Piotrowski View biography
Mandy Piotrowski is a Chicago native with a passion for mundane and bizarre history. Having grown up in the city, she now splits her time between Chicago and Milwaukee doing museum and local walking expeditions. She is certified in D.C. and New York City, is a certified International Tour Manager through the International Guide Academy in Denver, and has written various walking programs for Chicago, ranging from art history to women's history to city history.
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.
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.
Duration
6 days
5 nights
What's Included
11 meals ( 5B, 3L, 3D )
2 expert-led lectures
6 expert-led field trips
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
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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.
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.
Activity Note
Getting on/off motorcoach. 6 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 guide. 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.
Activity Note
Getting on/off boat. Activity level is dependent on individual pursuits during free time.
Breakfast:
Hotel buffet.
Morning:
We begin our day riding the motorcoach 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:
Free time. This period of time has been set aside for your personal independent exploration to see and do what interests you most. Please refer to the list of Free Time Suggestions in your preparatory materials. The Group Leader will be happy to offer suggestions. Dinner is on your own this evening. Chicago has a vibrant local food scene; please see the Restaurant Suggestions in your preparatory materials.
Dinner:
On your own
Evening:
At leisure.
Activity Note
Getting on/off motorcoach. Driving up to 15 miles to historic Oak Park. Walking up to 1 mile exploring this neighborhood. 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.
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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MEALS
11 Meals
5 Breakfasts
3 Lunches
3 Dinners
The following choices may be available when requested in advance: Gluten Free, Gluten Free
LODGING
Lodgings may differ by date. Select a date to see the lodgings specific to that date.
Showing Lodging For:
Oct 12, 2025 - Oct 17, 2025
  • Oct 12, 2025 - Oct 17, 2025
  • May 04, 2025 - May 09, 2025
  • Jun 15, 2025 - Jun 20, 2025
  • Aug 10, 2025 - Aug 15, 2025
  • Oct 12, 2025 - Oct 17, 2025
5 nights
Location: Chicago
The attentive amenities at Hyatt Place make us one of the best Chicago River North hotels. During your stay, a Host will happily assist you with orders from our new Gallery Menu, Fresh 24/7, featuring our signature flatbreads, a Make It 2 option, and delicious new sandwiches, greens, apps & more. Or you can enjoy specialty Starbucks® coffee, premium beer, wine & cocktails over friendly conversation at the intimate Bakery Café. In addition to on-site dining options, our LEED-Certified hotel in Downtown Chicago offers perks such as free Wi-Fi, a 24-hour Stay Fit Hyatt fitness center, laundry and dry cleaning service, amazing views of the city, and much more. Whether traveling for business, pleasure, or a bit of both, look no further than our River North area hotel.
5 nights
Location: Chicago
The attentive amenities at Hyatt Place make us one of the best Chicago River North hotels. During your stay, a Host will happily assist you with orders from our new Gallery Menu, Fresh 24/7, featuring our signature flatbreads, a Make It 2 option, and delicious new sandwiches, greens, apps & more. Or you can enjoy specialty Starbucks® coffee, premium beer, wine & cocktails over friendly conversation at the intimate Bakery Café. In addition to on-site dining options, our LEED-Certified hotel in Downtown Chicago offers perks such as free Wi-Fi, a 24-hour Stay Fit Hyatt fitness center, laundry and dry cleaning service, amazing views of the city, and much more. Whether traveling for business, pleasure, or a bit of both, look no further than our River North area hotel.
5 nights
Location: Chicago
The attentive amenities at Hyatt Place make us one of the best Chicago River North hotels. During your stay, a Host will happily assist you with orders from our new Gallery Menu, Fresh 24/7, featuring our signature flatbreads, a Make It 2 option, and delicious new sandwiches, greens, apps & more. Or you can enjoy specialty Starbucks® coffee, premium beer, wine & cocktails over friendly conversation at the intimate Bakery Café. In addition to on-site dining options, our LEED-Certified hotel in Downtown Chicago offers perks such as free Wi-Fi, a 24-hour Stay Fit Hyatt fitness center, laundry and dry cleaning service, amazing views of the city, and much more. Whether traveling for business, pleasure, or a bit of both, look no further than our River North area hotel.
5 nights
Location: Chicago
The attentive amenities at Hyatt Place make us one of the best Chicago River North hotels. During your stay, a Host will happily assist you with orders from our new Gallery Menu, Fresh 24/7, featuring our signature flatbreads, a Make It 2 option, and delicious new sandwiches, greens, apps & more. Or you can enjoy specialty Starbucks® coffee, premium beer, wine & cocktails over friendly conversation at the intimate Bakery Café. In addition to on-site dining options, our LEED-Certified hotel in Downtown Chicago offers perks such as free Wi-Fi, a 24-hour Stay Fit Hyatt fitness center, laundry and dry cleaning service, amazing views of the city, and much more. Whether traveling for business, pleasure, or a bit of both, look no further than our River North area hotel.
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