DAY 1
Check in to one of Chicago's waterfront hotels, offering terrific views of the Chicago River or Lake Michigan.
To get a good look at Chicago's imposing presence, visit the Sears Tower Skydeck, one of the world's tallest buildings. Besides being an example of Chicago's amazing architecture, the view gives a sense of the size of Lake Michigan (truly a "Great Lake!").
You can also wander at will 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, rock fragments from the Alamo, the Coliseum and the Chinese Wall.
For an up-close look at Chicago's past and present, visit the permanent and visiting exhibitions at the Chicago History Museum, a museum focusing on Chicago and American history.
In the evening, enjoy one of the city's great River North area restaurants such as Harry Caray's or maybe something a little more exotic like Vong's Thai Kitchen or Nacional 27, a Nuevo Latin supper club.
DAY 2
Begin a beautiful spring day with a classic American-style breakfast at a local diner, like Ed Debevic's , Lou Mitchell's or Ada's Deli, followed by a walk to the Chicago River for a boat tour on Chicago's First Lady or Chicago's Little Lady.
Travel along the river, while knowledgeable, volunteer docents from the Chicago Architecture Foundation share the sites and offer an unmatched look at the city. If you don't want quite so much architectural detail, Mercury Cruise Lines runs narrated cruises out on the Lake that offer splendid skyline views.
Spend the rest of the day on foot, stopping for a light lunch en route to the next stop. Downtown in the Loop, take a look at some of the city's breathtaking outdoor sculpture by Picasso, Chagall, Calder and Miro among others.
Later, stop at the Chicago Cultural Center to see one of their latest exhibitions, and end the day dining at an outdoor café, watching the world go by - Chicago style.
DAY 3
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.
Ride back into Chicago and enjoy the view from the train offering 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 and 96th floors of the John Hancock Center.
DAY 4
Visit The Art Institute of Chicago, where among more than 300,000 works you can see one of the finest collections of impressionist and post-impressionist paintings in the world. Then head to River North - Chicago's best-known gallery district.
After a delicious lunch, visit the Mexican Fine Arts Center Museum and discover the Mexican-American neighborhood of Pilsen. That evening, depart for a trip through the Great Lakes region to continue your true North American experience.