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Chicago is home to architectural feats by Frank Lloyd Wright, Mies Van der Rohe and so many other influential architects. Very few other cities offer the abundance of art in both public and private spaces. This three-day itinerary offers you a glimpse into the art and architectural heritage of the city designed to be Paris on the Prairie.
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Check into one of Chicago's waterfront hotels, offering terrific views of the Chicago River or Lake Michigan. To get a good look at the magnificent presence of Chicago and Lake Michigan, visit the Sears Tower Skydeck, the highest observatory in Chicago atop North America's tallest building. Walk the streets and see styles from Beaux Arts to Art Deco, Gothic to Mies van der Rohe. Close to the Chicago River (the only river in North America that flows backwards from the lake), you'll find the Wrigley Building and the Tribune Tower, whose walls are studded with many famous stones culled from all over the world, including a moon rock and fragments from the Alamo, the Coliseum and the Great Wall of China. For an up-close look at Chicago's past and present, visit the Chicago History Museum. Head to River North for fantastic restaurants such as Harry Caray's, or on the exotic side, Vong's Thai Kitchen or Nacional 27, a Nuevo Latino supper club. 
Begin a beautiful summer day with a classic American-style breakfast at Ed Debevic's, Lou Mitchell's or Ada's Famous Deli & Restaurant, followed by a Chicago River boat tour on Chicago's First Lady or Chicago's Little Lady. Knowledgeable docents from the Chicago Architecture Foundation share the sights and offer an unmatched look at the city. If you don't want quite so much architectural detail, Mercury Skyline Cruiseline runs narrated lake cruises with splendid skyline views. Spend the rest of the day on foot, stopping for a light lunch en route to the next destination. Downtown in the Loop you'll find outdoor sculpture by Picasso, Chagall, Calder and Miró, among others. Stop at the Chicago Cultural Center to see its latest exhibition, and end the day dining at an outdoor café, watching the world go by Chicago-style. 
Buy a visitor pass for the Chicago Transit Authority (CTA), Chicago's easy-to-navigate public transit system. Ride out to Oak Park on the "El", Chicago's elevated rail system, and visit the Frank Lloyd Wright Home and Studio, and the Prairie School National Historic District. The view from the train offers a unique close-up of the buildings and parks that make up this great city. Enjoy dinner and late-night drinks at The Signature Room, which sits on the 95th floor of the John Hancock Center. 
Visit The Art Institute of Chicago, where among the more than 300,000 works you can see one of the finest collections of Impressionist and Postimpressionist paintings in the world. Then head to River North, Chicago's best-known gallery district. After lunch, visit the National Museum of Mexican Art in the Mexican-American neighborhood of Pilsen. That evening, depart for a trip through the Great Lakes region to continue your North American journey.
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