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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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Prefer to enroll or inquire by phone? 800-454-5768
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Prices displayed below are based on per person,doubleoccupancy.
DATES & starting prices
PRICES
Filling Fast!
May 4 - May 9, 2025
Starting at
2,349
Filling Fast!
May 11 - May 16, 2025
Starting at
2,349
May 18 - May 23, 2025
Starting at
2,349
Jun 8 - Jun 13, 2025
Starting at
2,349
Jul 13 - Jul 18, 2025
Starting at
2,349
Aug 10 - Aug 15, 2025
Starting at
2,349
Sep 14 - Sep 19, 2025
Starting at
2,349
Sep 28 - Oct 3, 2025
Starting at
2,349
Oct 5 - Oct 10, 2025
Starting at
2,349
DATES & starting prices
PRICES
May 4 - May 9, 2025
Starting at
2,799
May 11 - May 16, 2025
Starting at
2,799
May 18 - May 23, 2025
Starting at
2,799
Jun 8 - Jun 13, 2025
Starting at
2,799
Jul 13 - Jul 18, 2025
Starting at
2,799
Aug 10 - Aug 15, 2025
Starting at
2,799
Filling Fast!
Sep 14 - Sep 19, 2025
Starting at
2,799
Sep 28 - Oct 3, 2025
Starting at
2,799
Filling Fast!
Oct 5 - Oct 10, 2025
Starting at
2,799
This date is available to book as a private experience for your group!

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.

Best of all, you’ll…

  • 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
Zbigniew Banas
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.

Please note: This expert may not be available for every date of this program.

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.
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
12 meals ( 5B, 4L, 3D )
2 expert-led lectures
8 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
Walk four blocks to dinner and back
Afternoon:
Program Registration begins at 3:00 p.m in the hotel lobby. Please join us at the Road Scholar table to register with the program staff, get any updated information, and confirm the time and location of the Orientation session. Hotel check-in is at 4:00 p.m. If you arrive late, please locate your Group Leader and let them know you have arrived. 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. In addition to our experienced and knowledgeable Group Leader, we will learn from a series of local experts who will give lectures and lead field trips. Program-related travel and transfers will be via private motorcoach unless noted otherwise. Meals will feature local cuisine in a variety of settings. Periods in the 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.
Dinner:
Dinner at a local restaurant
Evening:
At leisure. Continue getting to know your fellow Road Scholars, settle in, and get a good night's rest for the day ahead.
Activity Note
Getting on/off a motorcoach multiple times throughout the day; walking up to 3 miles; driving through the city, approximately 2.5 hours total riding time.
Breakfast:
At the hotel.
Morning:
At the hotel, we will have an expert-led lecture on the history of the Chicago area from the early indigenous people through the Great Migration. We will then board our motorcoach for a city field trip. 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 go on 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.
Lunch:
At a popular local restaurant.
Afternoon:
After lunch we will visit the DuSable Museum of African American History. Founded in 1961 by Dr. Margaret Burroughs and her husband, Charles, the DuSable is the oldest museum of African American history in the country. We will return to the hotel in the late afternoon.
Dinner:
This meal has been excluded from the program cost and is on your own to have what you like. The Group Leader will be happy to offer suggestions.
Evening:
At leisure.
Activity Note
Getting on/off a motorcoach; driving 15 miles, about 75 minutes hours total riding time. Walking and standing at museum is dependent upon personal preference; up to two hours.
Breakfast:
Breakfast at the hotel.
Morning:
We will start the day with an expert presentation on the fascinating world of Chicago Politics. Then we will take the motorcoach to explore more of Chicago. We 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, including Millennium Park which won the Rudy Bruner Award for Urban Excellence.
Lunch:
Lunch at the Chicago History Museum.
Afternoon:
After lunch, we will go on an expert-led field trip at the Chicago History Museum. This institution houses 22 million historical artifacts and documents from Chicago and U.S. history, with an emphasis on these main areas: Living/Working/Governing in the Metropolitan Area, the Built Environment, and Individuals and Ideas. We will gain a better understanding of Chicago’s past, its present, and prospects for the future.
Dinner:
On your own to enjoy local fare.
Evening:
At leisure.
Activity Note
Getting on/off a motorcoach. Walking 2 blocks to/from the boat. Getting on/off a boat; cruising approximately 1.5 hours. Walking and standing a minimum of 1 hour in the museum.
Breakfast:
Breakfast at the hotel.
Morning:
This morning we will enjoy an architectural boat cruise on the Chicago River. None other than Frank Lloyd Wright said, “It [modern architecture] all started here….” Our study cruise this afternoon presents more of Chicago’s extraordinary architecture and related social history. 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 one of the world’s largest commercial buildings. Chicago also has more moveable bridges than any city in the world including an engineering wonder, the Michigan Avenue Bridge, one of the city’s foremost thoroughfares. We’ll learn about all this and much more during this cruise with expert commentary. Afterwards, we will depart the dock for lunch at the Field Museum.
Lunch:
Lunch at leisure at the Field Museum. Vouchers will be distributed.
Afternoon:
The Field Museum of Natural History is widely regarded as one of the finest natural history museums on the world. It originated in 1893 as the Columbian Museum of Chicago. The name was later changed to honor the generosity of benefactor and department store founder Marshall Field, and to better reflect a focus on the natural sciences. During a self-directed exploration, we’ll learn about the museum’s work and collections. Please note: The Field Museum does not have docents except for school groups. Please use the supplied map to direct your independent exploration. You will have ample time to delve into exhibits that interest you. Among its collections, you can learn about gems, dinosaurs, mummies, Africa, the Pacific, the Ancient Americas, Native Voices, and much more. The lakefront campus is also home to the Adler Planetarium and the Shedd Aquarium, together regarded as among the finest of their kind in the world. The motorcoach will depart the Field Museum at 4:00 p.m. You are welcome to stay and continue exploring or you may return to the hotel for an afternoon and evening on your own. If you choose to remain at the museum, you will need to find transportation back to the hotel, at your expense.
Dinner:
At a local restaurant.
Evening:
At leisure.
Activity Note
Getting on/off a motorcoach. Walking up to two miles on the Mural Exploration; Walking and standing a minimum of 1 hour at the Art Institute.
Breakfast:
Breakfast at the hotel.
Morning:
We are joined by a local expert as we visit the some of the extraordinary street art in Chicago. Along the way, we’ll learn unique details about Chicago’s history and discover uplifting elements about the artists and the city. This is an upbeat exploration that shares how artists have improved neighborhoods one mural at a time.
Lunch:
At a local restaurant within a short drive of the Art Institute of Chicago.
Afternoon:
After lunch, we will 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. Return to the hotel in late afternoon.
Dinner:
At a neighborhood restaurant. Share favorite experiences and enjoy camaraderie with new Road Scholar friends during our farewell dinner.
Evening:
At leisure. Prepare for check-out and departure in the morning.
Breakfast:
Breakfast at the hotel.
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 rewarding programs 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
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.
Showing Lodging For:
May 04, 2025 - May 09, 2025
  • May 04, 2025 - May 09, 2025
  • May 04, 2025 - May 09, 2025
  • May 11, 2025 - May 16, 2025
  • May 18, 2025 - May 23, 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
Location: Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Location: Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Location: Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Location: Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Location: Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Location: Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Location: Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Location: Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
5 nights
Location: Chicago
Business Center, Exercise Room, Complimentary Breakfast, Convenience Store, Complimentary High Speed Internet
Participant Reviews
4.96
Based on 31 Reviews
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Suzanne – Class of 2023 | Asheville, NC
This trip exceeded my expectations. Chicago is a beautiful, clean city with stunning architecture, numerous parks, trees and flowers, and world-class museums. The speakers were knowledgeable and entertaining and enhanced my understanding of the city. Our group leader, Kim Johnson, was just the best. She added to my enjoyment of this trip immensely.
— Review left September 11, 2024
John – Class of 2021 | Waterford, NY
We are still talking about our trip experience; it was exceptional and hit all of our "must see/do things" on our first trip together to Chicago. Our trip leader Kim was exceptional, and an asset to Road Scholar. Her enthusiasm and attention to detail made it worth the trip.
— Review left September 11, 2024
Janice – Class of 1998 | Jacksonville, FL
This was a good trip - learning about Chicago was especially delightful because our guides and "local experts" all love the city, and constantly told us how much they love the city. We spent a lot of time at the South side museum and touring the neighborhood on the first day. Then it sort of accelerated, and by the last day, when we finally got to the Art Institute of Chicago, we were exhausted! We only had a few hours there. The mural tour was canceled by a no-show guide; but it was better, actually, because it was VERY hot, the tour would have been mid-day. Tony, our Ass't guide took us to two beautiful historic buildings (original library for one) - much better than the mural outside tour. The lunches were delicious and exciting - as they were scheduled during the bus tours in places we wouldn't have found on our own. Speaking of "on our own"-- the Friday and Saturday night (2nd and 3rd nights) we were "on our own." I didn't like it. I called RS ahead, asking about it, and they referred me to the local guide, Andrea, who said it was a good opportunity to explore. Sorry, alone in a new city, knowing no one- not even other Road Scholars, I didn't WANt to explore. So no dinner Friday night. Saturday night I ate Subway near the hotel. Andrea did book a table for 8 each night, but there were 30 of us and I wasn't quick enough to elbow my way to the sign-up sheet. This was very disappointing -- as Chicago seems to have wonderful eateries. We could have had a meeting to see who wanted to join together - but that didn't happen. The two group meals we did have were served family style and were fantastic. Still, Road Scholar Signature Cities are a good way to meet new cities.
— Review left July 21, 2024
Marcia – Class of 2019 | King William, VA
It was nice to see Chicago and learn about it's history. Met some lovely, interesting people. The things we saw were varied and impressive. It's a nice tour if you want to see and get a taste of Chicago in four days.
— Review left July 13, 2024
George – Class of 2000 | Crestview Hills, KY
For those wishing to get a well-organized introduction to Chicago's history, politics, culture, ethnic neighborhoods and unique style, this is your program. Our group leaders and instructors, some of them life-long Chicagoan's, were very knowledgeable and responsive to the plethora of questions posed to them. The program provides a great introduction to several of the city's wonderful museums and provides an opportunity to sample some of its many excellent eateries. One will have several opportunities to check out the city's expansive and reasonably priced public transportation. My favorite activity was the boat ride on the Chicago River that introduced us to the city's amazing architecture. Many of my fellow Road Scholars commented on the cleanliness of the city and the general courteousness of its drivers. The city serves as a big draw to young college graduates from all over the Midwest, so one shouldn't be too surprised by the large number of young adults present in the city. Overall, the city does exude a level of energy which derives in part from it demographics and the love its many lifelong residents have for all that is Chicago.
— Review left June 28, 2024
Susan | Amherst, NH
Our trip to Chicago was AMAZING! We learned so much about the city and got to see world-class art at the Art Institute. Visiting the Field Museum was on my bucket list and it did not disappoint. This was my first Road Scholar trip. The leaders and balanced programming mean that it will be the first trip of many.
— Review left June 19, 2024
Gary – Class of 2018 | Laguna Niguel, CA
The perfect introduction to this major city. Whetted my appetite for a return to Chicago!
— Review left June 19, 2024
Elissa – Class of 2013 | Raleigh, NC
A pack-filled and comprehensive tour of Chicago by a wonderful group leader and excellent speakers. Hotel in a great location and wonderful meals around town.
— Review left May 18, 2024
David – Class of 2018 | Novato, CA
Great overview of Chicago.
— Review left May 15, 2024
Kari – Class of 2010 | Middletown, CT
Chicago is a beautiful city and has much to offer, and we learned about the development of the city from the beginning.
— Review left October 23, 2023
Gary – Class of 2021 | Greenwood, IN
Chicago in autumn.... how interesting. Our group had a wonderful program highlighted by an architectural boat ride on the Chicago River showing(through various buildings) the history of this most interesting city. We highly recommend this program if you're interested in understanding a bit about our US history.
— Review left October 19, 2023
Evelyn – Class of 1998 | Greenwood, IN
As close as we have lived from Chicago (4 hours drive), we never have taken the time to really APPRECIATE Chicago. This is the program which will help you truly get a basic understanding of Chicago and its influence on the United States and the world. I LOVED the instructors because they OBVIOUSLY love Chicago. I loved the program because it gave us good reasons to really love our "Paris of the Prairie"..... Chicago.
— Review left October 18, 2023
Patricia – Class of 2016 | Decatur, GA
This was my ninth Road Scholar trip. I would rank it in the top three trips!
— Review left October 18, 2023
Judith – Class of 2023 | Scarsdale, NY
Intersting and educational trip to Chicago.Friendly fellow travelers and wonderful leaders.
— Review left October 18, 2023
Martha – Class of 2021 | Shoreline, WA
The Signature City Chicago is a short, wonderful view of the River North area of Chicago. It is packed with history, good restaurants and walkable, interesting museums, buildings, and neighborhoods. I highly recommend it!
— Review left September 16, 2023
Ron | Portland, OR
Chicago was indeed "Paris on the Prairie". It was more beautiful walkable, better landscaped, cleaner and safer than I had expected. Cultural amenities abound, and food choices are excellent. For someone looking for an excellent urban experience I highly endorse Chicago.
— Review left September 16, 2023
Yvonne – Class of 2014 | New York, NY
This is a most enjoyable, comprehensive and yet detailed program that I highly recommend
— Review left August 2, 2023
This participant did not give a star rating.
Linda – Class of 2005 | Austin, TX
Another good Road Scholar trip. We especially liked the free time in the Field Museum. Rick Bayless' La Frontera is in the same block as the hotel: excellent dinner there. Nice variety of food and eating places. Excellent guides.
— Review left June 30, 2023
Earl | Wynnewood, PA
At 90 a final revisit to a city we both love. We couldn't have had a more positive experience.
— Review left May 25, 2023
Frances – Class of 2015 | Cary, NC
The Signature City: Chicago program was excellent and informative. Our guide, Aurora Cruz Nelson, was skilled in shepherding a large group of 32, always available, and unfailingly upbeat and positive. Highlights were docent lectures, a bus tour of Chicago, a river canal architecture cruise, the Chicago Art Institue, and meals (good!). We didn't have as much time at the Field Museum of Natural History as I would have liked, but participants were free to stay after the coach departure and return to the hotel at their leisure. Chicago is a stunning, well-planned city, and now I've seen much more of it than the O'Hare airport.
— Review left May 16, 2023
This participant did not give a star rating.
Margaret – Class of 2017 | Concord, NH
We were so disappointed in this trip. Squeezing in 35 people with one person running the trip is an example of money over quality. There is no way for a restaurant to prepare a flavorful meal for 35 people during their dinner hour. We can go to art and history museums in any major city or on our own. What we were looking for is what make Chicago stand out as a vibrant city. What we received was apathy. Honestly, if you can't staff the program appropriately or put in some effort, cancel it rather than lower your standards. Unfortunately, we will not be back to Road Scholar anytime soon.
— Review left October 30, 2022
Susan – Class of 2015 | Henrico, VA
Chicago is a great mix of fabulous architecture, an impressive Art Institute, varied museums, interesting history and great ethnic restaurants. Signature City Chicago program will give you a well rounded introduction to all these aspects. The visit to the Federal Reserve Bank did not happen despite being on the Road Scholar website itinerary.
— Review left June 10, 2022
John – Class of 2014 | The Villages, FL
Great architectural tour of the city. I learned a lot
— Review left May 17, 2022
Elizabeth – Class of 2016 | Colorado Spgs, CO
I always loved Chicago but I appreciate it so much more after this program. We would highly recommend this to anyone wanting to learn about the foundations that made Chicago the grand city it is today.
— Review left November 3, 2021
Robert – Class of 2011 | North Canton, OH
If you're interested in Chicago's history, architecture and politics as presented by very interesting and qualified lecturers, this program is for you.
— Review left November 3, 2021
Nancy – Class of 2015 | Somerset, NJ
Signature City Chicago was wonderful with a nice variety of experiences. Instructional as well as in person
— Review left October 27, 2021
Mary Lynn – Class of 2015 | Missoula, MT
Chicago is a clean, safe and beautiful city. There is so much to do on this program and some extra time to do other things. I didn't feel like I was in a big city. There were not too many people or cars. I also didn't feel suffocated by the big buildings. There is lots of green space in Chicago. The people we met were nice and friendly. We went in October and the weather was great. The food was very good and there were all kinds of other restaurants near our hotel. There were also other stores in case something was forgotten. I also thought the prices for things was reasonable.
— Review left October 27, 2021
Rutie – Class of 2019 | Rockville, MD
RoadScholar does the work for you. From finding excellent and fascinating speakers, arranging your time and leaving enough time to explore on your own, and they paid especially much attention to ensure that the leaders were wonderful. If you get to tour with Mary Ann and Mike Savage you'll know what I mean.
— Review left November 17, 2019
This participant did not give a star rating.
Raymond – Class of 2018 | Denver, CO
Although the weather did not cooperate (cloudy/rainy) the tour was what I expected. The highlights were the architectural river cruise (the guide was fantastic), the Field Museum, and of course the Art Institute. Our tour guides, Arlene and Nancy, were knowledgeable and personable. The hotel was nicely located north of the river, making it easy to get around. The service was very slow for breakfast making early morning lectures a challenge to get to. The two lectures were excellent. The bus on our 1st full day had no air conditioning (broken) which caused some people discomfort. All together the windy city came out looking pretty good.
— Review left July 1, 2019
Kathleen – Class of 2018 | Oakland, CA
This program provides an excellent overview of Chicago and offers a diverse introduction to this fascinating city.
— Review left June 19, 2019
Michelle – Class of 2018 | Sacramento, CA
This was a delightful program in a phenomenal city! The variety of fascinating sites and activities, the group leaders and instructors, and the lodging were wonderful. There is some free time on this program for a customized experience. We recommend staying in Chicago additional days, as there is so much to do and see. Be prepared for variable weather. And tons of fun!
— Review left June 2, 2019





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