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Chicago Itineraries
- Art & Architecture
- Shopping & Culture
- Big Hits In The Big City
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.
Day 1
Daytime
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 in beautiful Lincoln Park. Wander the streets in the nearby Gold Coast to view various architectural styles ranging from the late 1800s to the present coexisting in one of Chicago’s most affluent neighborhoods.
Evening
Head to River North for fantastic restaurants such as Harry Caray's for a real Chicago steakhouse experience with a focus on old Chicago and Chicago sports and Mambo Grill for zesty Latin food, or check out the scene and sushi at Japonais, located in the former warehouse of mail order catalog giant Montgomery Ward, recently converted to condominiums, restaurants and retail.
Day 2
Daytime
Begin a beautiful summer day with a classic American-style breakfast at Ed Debevic's or Lou Mitchell's, followed by a Chicago River boat tour on Chicago's First 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.
Evening
Enjoy dinner and late-night drinks high above Chicago at The Signature Room, which sits on the 95th floor of the John Hancock Center. Here you can see Chicago beautifully stretched out before you. Can you see a couple of the places you have already visited?
Day 3
Daytime
Visit the Art Institute of Chicago, where among the more than 300,000 works of art 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 lunch, visit Chicago’s newest cultural icon, Millennium Park. This 24.5-acre park features the work of world-renowned architects, planners, artists and designers. Among Millennium Park's prominent features are the Frank Gehry-designed Jay Pritzker Pavilion, the most sophisticated outdoor concert venue of its kind in the United States; the interactive Crown Fountain by Spanish artist, Jaume Plensa; the contemporary Lurie Garden designed by the team of Kathryn Gustafson, Piet Oudolf and Robert Israel; and UK artist, Anish Kapoor's, hugely popular Cloud Gate sculpture, nicknamed “The Bean” by locals.
Evening
After dinner this evening, end your visit with some Chicago Blues at Blue Chicago or Buddy Guy's Legends. Make a note to come back again soon!
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