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Travel By Design: Wright in Chicago

Experience Chicago through the eyes of Frank Lloyd Wright!

Wednesday, September 24 – Sunday, September 28

We’re teaming up with Twin Travel Concepts for a unique Chicago getaway that takes you to the roots of Frank Lloyd Wright’s genius. This trip is all about exploring the places where Wright’s style first took shape—the very origin story of the architect we know today.

We’ll visit his Home and Studio, Unity Temple, and the Robie House, plus enjoy private tours and lunches at the Arthur Heurtley and Avery Coonley Houses. In Oak Park, we’ll take a guided walking tour through Wright’s earliest residential masterpieces, giving you a front-row seat to how his groundbreaking Prairie style evolved.

Along the way, you’ll enjoy a private evening reception at H.H. Richardson’s Glessner House, an inspiring Art Deco walking tour, and the classic Chicago Architecture River Cruise to see the city from a fresh perspective.

You’ll stay four nights at the artsy 21c Museum Hotel, with comfy coach rides between all the stops. Space is limited—don’t miss this chance to see how Wright’s vision started and why Chicago is still at the heart of his legacy.

Here is a more detailed itinerary of the daily activities:

Wednesday, September 24

Group will check in at 21c Museum Hotel Chicago, a gorgeous art-themed hotel in the heart of downtown Chicago.

For dinner, we will enjoy the nearby Osteria Via Stato, an Italian restaurant known for its elegant family-style menu.

Thursday, September 25

Enjoy an included breakfast at our hotel, then meet at the coach as we begin our day with a visit to Unity Temple in Oak Park, IL, one of Frank Lloyd Wright’s most iconic masterpieces.

Built between 1905 and 1908, this Unitarian Universalist church highlights Wright’s Prairie School style with its striking geometric forms, innovative use of reinforced concrete, and masterful play of light and space.

Next, we’ll take an audio-guided walking tour through Oak Park’s Frank Lloyd Wright Historic Neighborhood, home to the world’s largest collection of Wright-designed buildings. Together, we’ll explore how Wright’s style evolved between 1889 and 1909 and discover the roots of American residential architecture.

For lunch, we’ll enjoy a delicious meal at Rustico, a vibrant Oak Park restaurant known for its fusion of Spanish and Italian cuisine, including award-winning tapas, paella, and wood-fired pizzas.

In the afternoon, we’ll tour the Frank Lloyd Wright Home and Studio. We’ll walk through Wright’s 1889 home and adjoining studio, restored to their 1909 appearance and carefully preserved by the Frank Lloyd Wright Preservation Trust. This visit will give us a fascinating glimpse into Wright’s life and the beginnings of his Prairie style.

We’ll then visit Glessner House, a stunning Gilded Age mansion designed by Henry Hobson Richardson in the 1880s. We’ll dive into the lifestyle of Chicago’s elite in the late 19th century. Our tour will end with a cocktail reception with hearty hors d’oeuvres in the courtyard.

Friday, September 26

Enjoy breakfast at the hotel, then meet our coach as we begin our day with a visit to the Robie House, a masterpiece of Prairie School architecture designed by Frank Lloyd Wright.

Completed in 1910 in Chicago, this stunning home features strong horizontal lines, cantilevered rooflines, and bands of art glass windows, perfectly embodying Wright’s vision of harmonizing architecture with the natural landscape.

For lunch, we’ll visit the Arthur Heurtley House, one of Wright’s earliest fully realized Prairie-style homes, built in 1902. This unique design showcases horizontal lines, overhanging eaves, and the striking use of Roman brick, highlighting Wright’s signature organic approach to architecture. We’ll enjoy a guided tour of the home, where living and dining areas are on the second floor. On-site lunch will be provided.

In the afternoon, we’ll embark on a 90-minute Chicago Architecture Center cruise led by expert docents. As we relax aboard a luxurious boat with open-air decks and climate-controlled cabins, we’ll pass by and learn about over 50 iconic buildings, including the Willis Tower, Wrigley Building, and John Hancock Center. Our guides will share fascinating stories about the history, design, and architects behind Chicago’s most famous structures.

The evening is yours to enjoy at your leisure.

Saturday, September 27

Enjoy breakfast at our hotel, then meet your coach as we begin our day with a visit to the Charnley-Persky House, a historic architectural landmark designed by Louis Sullivan and Frank Lloyd Wright between 1891 and 1892. This pivotal work of modern architecture showcases Sullivan’s ornamental style alongside Wright’s early design principles. We’ll enjoy a guided tour that highlights the significance of this unique collaboration.

For lunch, we’ll visit the Avery Coonley House, one of Frank Lloyd Wright’s most elaborate Prairie-style residences, built between 1908 and 1912. This sprawling estate features horizontal lines, overhanging eaves, and intricate art glass windows, all reflecting Wright’s signature architectural style. Commissioned by wealthy industrialists Avery and Queene Ferry Coonley, the home allowed Wright creative freedom to design a harmonious living space. We’ll explore the estate and enjoy lunch here.

In the afternoon, we’ll step inside the lobbies of five Art Deco masterpieces near the banks of the Chicago River. This 90-minute walking tour, curated by the Chicago Architecture Center, reveals how the lavish ornamentation of these buildings reflected the prosperity and optimism of the Roaring Twenties.

Dinner will be at Beatrix River North, where our group can also enjoy a robust wine and beer offering.

Sunday, September 28

Enjoy breakfast at our hotel. Afterward, you’ll check out at your own pace. Airport transfers will also be on your own, giving you the flexibility to plan your departure as you wish.

Cost includes hotel, motor coach travel for the duration of the trip, all tours and museum entrances, breakfast daily, 3 lunches, 1 reception, and 2 dinners. Airfare is not included. Optional travel protection will be available.

Double occupancy, per person: $2,430

Single occupancy, per person:  $3,010

See full trip details and register here!

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