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Chicago Vacations

The third most populous city in the United States, Chicago sits perched on Lake Michigan, its skyscrapers glistening above the horizon. The iconic John Hancock Center, sky-high Willis Tower and Tribune Tower rise above the city’s nearly three million residents.

Chi-town also possesses an abundance of culture, from its famed Second City improv and Tony Award® winning Goodman Theatre to the Art Institute of Chicago, boasting hundreds of impressionist paintings and more. 

Region: USA

Featured Chicago Hotel

The Drake Hotel

The Drake Hotel

  • AAA Four Diamond Hotel
Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.
Magnificent Mile, Chicago, IL

This acclaimed hotel commands a pride of place on Chicago's Magnificent Mile, affording guests easy access to the city's most exclusive shopping, nightlife and dining.

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From masterful Frank Lloyd Wright buildings such as the Rookery and Robie House to the remarkable Museum of Science and Industry, Aqua Tower and St. John Cantius Church, Chicago’s architecture is one of the city’s grandest achievements. Vacationers can tour these gems and more.

Lake Shore Drive is also worth a look. Chicago’s impressive lakefront bicycle trail stretches from the Indiana border up to Evanston, Illinois, passing through scenic parklands, universities and the Lincoln Park Zoo.

A drive past more than fifteen miles of beaches, skyscrapers and urban green space offers a superb view of the Windy City from ground level; while a peek from high atop the country’s second tallest building, the Willis Tower, offers magnificent panoramic views of four different states.

What To Do

Let the comedic masters of Second City, whose former alumni include such comic legends as Tina Fey, Stephen Colbert, and Steve Carell, tickle your funny bone with sketches, songs, and improvisations.

Watch the Chicago Cubs play baseball at world-famous Wrigley Field.

Ride a speedboat along Lake Michigan from Navy Pier passing such renowned Chicago landmarks as the Willis Tower, Buckingham Fountain, and Grant Park.

Take in some of the city’s spectacular views on a bike ride along the lake’s 18-mile path. En route, visit the Lincoln Park Zoo.

Attend a free event at the Chicago Cultural Center. Get a panoramic view of the city and beyond from the 103rd floor Skydeck Chicago on Willis Tower. There are even glass balconies that extend out from the building for those daring to peek 1,353 feet to the ground.