Chicago, Illinois - Arts & Architecture in the Windy City

Be swept away by the Windy City on this whirlwind adventure to Chicago! Whether you’re biting into your first savory taste of Chicago deep dish pizza or feeling your stomach drop as you stare down 103 floors from the glass observation deck in the Willis Tower, this is a city of experiences, each one more potent than the last. Uncover the grit and romance of Chicago’s history as you tour the major landmarks of the city. Get behind the scene’s tours of Shedd Aquarium, The Art Institute, Millenium Park, and more.  Immerse yourself in the culture and beauty of a place known for its architectural innovation. Above all, allow yourself to be truly blown away - after all, it’s what Chicago is known for.

Day 1

Chicago: ARRIVE

Upon arrival in Chicago, “The Windy City,” you will be met and transferred from one of the airports to your hotel.  You’ll have some free time to relax and settle into your hotel room before meeting your group in the lobby for a welcome dinner at The Grill on the Alley, a well-known steakhouse with a classic American menu. Millennium Knickerbocker Chicago. (Welcome D)


Day 2

Chicago: Willis Tower/Theatre District/Chicago Riverwalk/Magnificent Mile

After breakfast, meet your local guide and begin your exploration of this exciting city. Take a short drive to the Willis Tower, formerly known as the Sears Tower, a 110-story building in the heart of downtown Chicago and the largest skyscraper in the city. Continue to the Theatre District to tour the Chicago Theatre, a lavish movie palace that was the largest space of its kind in America. After lunch, on your own, take a brief walk to the Chicago Riverwalk and embark on a riverboat tour by the Chicago Architecture Foundation, a nonprofit cultural organization founded in 1966. On this 90-minute tour you will learn how Chicago grew from a small settlement into one of the world’s largest cities. Afterward, disembark and walk to the Magnificent Mile, a 13-block strip showcasing stores, restaurants, hotels, and unique attractions and entertainment.

Millennium Knickerbocker Chicago. (B)


Day 3

Chicago: Lower West Side/TheMart/Second City

This morning, take a short drive to the Lower West Side in Pilsen. Explore the unique architecture and bold murals that mark the fronts of homes, railway passes, and storefronts. After lunch, continue to TheMART, the world’s largest commercial building, wholesale design center, and one of Chicago’s premier international business centers.  Later, visit Old Town and embark on a neighborhood walking tour with a member of The Second City, the world’s premier comedy club, theatre, and school of improvisation. Old Town is home to beautiful Victorian-era buildings, brick alleyways and narrow, tree-lined streets. After your tour, you’re free to grab a traditional Chicago-style pizza from one of the many pizzerias in the area, have a drink at some of the oldest bars in the city, or sit in and enjoy the music at a nearby blues or jazz club. Your evening is at leisure. Millennium Knickerbocker Chicago. (B)


Day 4

Chicago: Shedd Aquarium/Millennium Park/Art Institute of Chicago

Another exciting day is in store for you as you continue your exploration of Chicago. Begin with a guided tour of Shedd Aquarium, a not-for-profit organization founded by John G. Shedd. The aquarium is home to more than 32,000 animals. Learn about the many conservation efforts and ways the aquarium gives back to the community during your expertly guided tour. Discover a state-of-the-art collection of architecture, landscape design, and art as you continue to Millennium Park for a guided tour. Learn about its elusive history, and how architects, artists, and engineers collaborated with Chicago’s movers and shakers to transform an ugly railway and parking lot into the city’s most defining park. Walk to the Art Institute of Chicago, founded as both a museum and school of the fine arts in 1879. Enjoy a private tour of the institute as you take in the various art collections, both new and old, from across the globe. Tonight, enjoy a farewell dinner with your fellow travelers at Gibson’s Bar & Steakhouse. ROW HOTEL. (B,D)


Day 5

Chicago: DEPART


Sadly, it’s time to say goodbye to this amazing city!  Depending on your flight time, you may have the opportunity to continue to explore the city on your own before departing for the airport. (B)

Prices starting at $3,295. For further booking, date, and pricing info please contact info@classicescapes.


Does not include international or domestic flights. Prices are based on 10 or more travelers, and are subject to change.