Begin the ultimate Chicago architecture tour by jetting off to the Windy City. On your very first day, enjoy a tour of Millennium Park, home to a Frank Gehry-designed concert pavilion and so much more. Check into the Millennium Knickerbocker Hotel and enjoy dinner at the legendary Lawry’s Restaurant in McCormick Mansion. (D)
Day 2: Hyde Park, River Cruise & Navy Pier
Immerse yourself in all things Frank Lloyd Wright, beginning with a tour of the Rookery Library, designed by the master. You will be awed by the illuminating “light court” and its exquisite spiral staircase. Then, drive through Hyde Park – the jewel of Chicago’s lakefront and site of the 1893 World’s Fair. Then, it’s on to the Museum of Contemporary Art and a relaxing lunch in the Union League Club, a private city club founded in 1879 by elite businessmen. You’ll learn more about the fascinating history of Chicago on a Lake Michigan and Chicago River cruise, before time to refresh back at the hotel. Tonight, experience Navy Pier and dine at Riva Crabhouse as you watch the sun set over the lake. (B, L, D)
Day 3: Art Institute, Skydeck & 'Hamilton'
Begin the day with a tour of the Art Institute of Chicago – voted best in the world by TripAdvisor! For lunch, marvel at the incredible variety of Italian edibles in Eataly, Mario Batali’s delicious emporium. You’ll have plenty of time to take your pick! Continue on to the Chicago Skydeck in the John Hancock Building. At 90 stories high, it offers the best 360-degree views of the city. After that, drive the Gold Coast and see the Astor Historic District, home to elegant Victorian mansions and townhomes. You’ll also see the “Alexander Hamilton” sculpture by artist John Angel. Fittingly, tonight’s entertainment is a performance of the wildly popular musical, Hamilton, after dinner at Francesca’s Italian restaurant. (B, D)
Day 4: Loving Frank Lloyd Wright
The morning is yours to relax at your hotel or hit the nearby “Magnificent Mile” to shop. Lunch on your own, before heading out on a driving tour of Frank Lloyd Wright’s old stomping grounds in Oak Park and River Forest. You’ll see where Ernest Hemingway was born, and admire the buildings that evoke Wright’s “prairie spirit.” Then, tour the landmark Frank Lloyd Wright Home & Studio – a perfect example of the depth of Wright’s talent and principles. To top off the day, stop at Unity Temple, a Wright gem that has recently undergone a complete renovation! From there, you’ll head home, fully satisfied by your cultural immersion in the Windy City. (B)