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Discover Chicago, Illinois on a riverboat cruise

Illinois

3 Days in Chicago, Illinois: Must-See Places on Your First Visit

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  • States:
    Illinois

Get to know Chicago, an international city bubbling with culture, endless attractions and stunning architecture.

Spend three days along and near the Lake Michigan shoreline to scratch the surface of this multifaceted destination. Take a walk on an iconic pier, marvel at the city’s architecture from sky-high viewpoints, cheer on the home team, and let the local Midwestern hospitality guide you through the third-largest city in the USA.

Day 1: Scenic Activities Along the Lakeshore

Get your bearings via the Lakefront Trail. For 29 kilometers along Lake Michigan, you can bike, walk, run or skate to diverse neighborhoods, public beaches and fabulous parks. In Millennium Park, Chicago’s renowned public art and architecture are on display: Marvel at the immersive Cloud Gate sculpture, play in the Crown Fountain, stroll through Lurie Garden and take in a concert at Jay Pritzker Pavilion Bandshell.

A few blocks away, stroll The Chicago Riverwalk, an urban park and pedestrian trail that will lead you to the scenic Navy Pier. Spend some time exploring its array of attractions, dining options and shops, before surveying it all from above on the Centennial Wheel. Soaring to heights of nearly 60 meters, the Wheel offers visitors 360-degree views of Chicago’s skyline and Lake Michigan.

Biking alongside Lake Michigan on a spring day in Lincoln Park

Biking alongside Lake Michigan on a spring day in Lincoln Park
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Day 2: Must-Try Experiences in the Heart of Chicago

Spend time on The Magnificent Mile, a 13-block stretch of Michigan Avenue featuring more than 460 stores, 275 restaurants and 70 hotels. At Chicago Avenue, pose for a photo in front of the Historic Water Tower, a Gothic limestone building completed in 1869 and one of few buildings to survive the Great Chicago Fire of 1871.

At the iconic Willis Tower, step into The Ledge’s enclosed glass balconies jutting a thrilling 1.3 meters from the 103rd floor at Skydeck Chicago. Can’t get enough heights? Check out 360 CHICAGO’s TILT experience in the John Hancock Building, where the full-length windows tilt out from the 94th floor for astonishing, bird’s-eye views of the city below.

Experience a true American classic at Wrigley Field, home of Major League Baseball’s World Champion Chicago Cubs. Go behind the scenes during an official tour of the 1914 ballpark, or make time for a game.

A spectacular view from Skydeck Chicago

A spectacular view from Skydeck Chicago
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Day 3: Admiring Architecture and Museums

Book a tour via foot, bus, bike, boat or Segway to see the city’s famed architecture including skyscrapers, residential buildings, hotels and Frank Lloyd Wright-designed masterpieces. Then, it’s back to the lakefront to explore the cultural offerings of Museum Campus. See marine life at Shedd Aquarium, gaze at the stars at Adler Planetarium, or visit Sue, the largest and most complete T. Rex ever found, among an astounding 24 million objects at the Field Museum.

Back in Grant Park, the Art Institute of Chicago will amaze with its 300,000 works of art from around the globe, ranging from ancient to modern. Renowned masterpieces on display include A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat and American Gothic by Grant Wood.

End your day a short walk away at the Clarence F. Buckingham Memorial Fountain, a masterpiece of its own, and watch the water dance 45 meters into the air. Go at dusk in the warmer months, when light and music accompaniments begin.

An illuminated scene of Buckingham Fountain in the center of Grant Park

An illuminated scene of Buckingham Fountain in the center of Grant Park
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Getting There

Fly into O’Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Rent a car, hail a taxi, ride a bus or get into the city via the “L,” the rapid-transit rail system.

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