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Chicago Vacation Packages

A modern metropolis on the shores of Lake Michigan that’s defined by a love for fine art, baseball and the blues.

Stroll museums and parks filled with art, and catch live blues any night of the week in Chicago’s bustling Downtown district. Or catch a lively sports game in this home to the Cubs and White Sox baseball teams, and the Chicago Bulls basketball team.

This metropolis is the third largest city in America, but getting around is easy thanks to the efficient above ground train, the ‘L’. Get your bearings from the tallest skyscraper in the US, Willis Tower, which defines the city’s skyline. The viewing platform, 1,353 feet (412 meters) above the busy streets, offers unparalleled vistas of Lake Michigan, Navy Pier, and other main attractions. 

Lincoln Park, just north of downtown, has beaches, sporting grounds and landscaped gardens. Soak up the history of the Windy City at the Chicago History Museum, located on the southern end of the park. Take a stroll through the indoor gardens of the Lincoln Park Conservatory, or spend an afternoon at the Lincoln Park Zoo. This public zoo houses more than 1,000 animals. Brookfield Zoo, 12 miles west of the city center, is more than double the size and features dolphin displays, big cats, a variety of primates and more. 

Head back into the Loop district downtown for some of the best shopping in the city, along Michigan Avenue’s Magnificent Mile. It’s a good place for lunch or dinner, or people watching while you sip a coffee or beer. Just south of the Magnificent Mile is the expansive Art Institute of Chicago well worth a visit for its collection of European and American masterpieces that include Monet, Van Gogh, and much more. Nearby is Millennium Park, a meeting place with public art and spectacular summer concerts.  

Chicago’s Museum Campus is located in the South Loop, just a few miles by car or a few stops on the “L” from downtown. The Field Museum is filled with natural history, while the Museum of Science has interactive exhibits such as a mock coal mine and an airplane.

Some of America’s most influential figures came from Chicago. Visit the Ernest Hemingway Museum and House, where the famous writer was born. Architect Frank Lloyd Wright’s first house is in the pretty Oak Park neighborhood (called the Frank Lloyd Wright Home and Studio). He designed many houses and buildings in the area, including Unity Temple, considered one of his best. On your way back into town, stop off at the Garfield Park Conservatory, an urban oasis of rare and exotic plants.

No trip to Chicago would be complete without catching a baseball game at the legendary Wrigley Field. At night, head to Navy Pier, packed with lively bars and restaurants. Another option is to head out for a night of blues at one of Chicago's legendary clubs. Check out  B.L.U.E.S. near downtown on Chicago's north side or Kingston Mines a few miles north near Lincoln Park. Both of these long established venues have music every night of the week.

Accommodation in Chicago

You won't have any troubles finding the most suitable hotel in Chicago. Expedia's hotels guide offers 636 places to stay in Chicago to cater for people from all walks of life.

Discerning travelers who delight in the timeless traditions of class and style are sure to enjoy the Extended Stay America Chicago - Darien, at 2345 Sokol Court, and the Peninsula Chicago, at 108 East Superior Street. Another two premium accommodation options worth having a look at include the Waldorf Astoria Chicago and the Trump International Hotel & Tower Chicago.

Alternatively, stay near Art Institute of Chicago and make a reservation at the Peninsula Chicago, which is just 2 kilometres (1 mile) away. Also popular is the Waldorf Astoria Chicago, 2 kilometres (1 mile) from Art Institute of Chicago.


Chicago Vacation Packages


Top Hotel Deals

See all 876 Hotels in Chicago
C$96
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.4
of 5, from 456 reviews
3.0 out of 5.0

Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

C$163
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
4.2
of 5, from 2,579 reviews
4.0 out of 5.0

This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent Mile shopping, and Wrigley Tower.

C$89
Inn of Chicago

Inn of Chicago

162 E Ohio St, Chicago
3.6
of 5, from 1,936 reviews
3.0 out of 5.0

Inn of Chicago is a half-block from the Magnificent Mile and 2 blocks from the landmark Tribune Tower. Millennium Park, Navy Pier, and the Art Institute of Chicago are among the many attractions within 1 mile.

C$126
Warwick Allerton Hotel Chicago

Warwick Allerton Hotel Chicago

701 North Michigan Avenue, Chicago
4.0
of 5, from 2,542 reviews
4.0 out of 5.0

Located on Michigan Avenue in the middle of Chicago's Magnificent Mile, this 1920s Italian Renaissance hotel is surrounded by fashionable shops, 1 mile from Lake Michigan and the Art Institute.

C$135
Hard Rock Hotel Chicago

Hard Rock Hotel Chicago

230 North Michigan Avenue, Chicago
4.1
of 5, from 2,095 reviews
4.0 out of 5.0

On Michigan Avenue and across from Millennium Park, this rock-inspired hotel occupies the 36-story, Art Deco-style Carbide and Carbon Building in downtown's Loop; Macy's is a block away.

C$93
Chicago's Essex Inn

Chicago's Essex Inn

800 S Michigan Ave, Chicago
3.6
of 5, from 1,373 reviews
3.5 out of 5.0

Across from the greenery and attractions of Grant Park, the Essex Inn is 3 blocks from the Loop business district and Lake Michigan, 4 blocks from the Art Institute, and a mile from Loop theaters.

C$124
The Whitehall Hotel

The Whitehall Hotel

105 E Delaware Pl, Chicago
4.1
of 5, from 2,177 reviews
4.0 out of 5.0

Built in 1927, this Chicago hotel is one block from Michigan Avenue shopping and Rush Street restaurants and nightlife; Lake Michigan is within five blocks.

C$136
Hyatt Regency Chicago

Hyatt Regency Chicago

151 East Wacker Dr, Chicago
4.3
of 5, from 2,898 reviews
4.0 out of 5.0

This Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are less than a mile away.

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