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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.


Guide to Exploring Chicago


Top Hotel Deals

See all 803 Hotels in Chicago
C$152
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.4
of 5, from 396 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$155
Club Quarters Hotel, Central Loop

Club Quarters Hotel, Central Loop

111 West Adams Street, Chicago
4.2
of 5, from 2,046 reviews
4.0 out of 5.0

Club Quarters is a club-like hotel in the center of the Loop, Chicago’s central business district. A short walk to Symphony Center, the Art Institute, Board of Trade, Willis Tower, Grant Park and the Riverfront, the Theatre District and Magnificent Mile.

C$209
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
4.2
of 5, from 2,558 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$182
The Whitehall Hotel

The Whitehall Hotel

105 E Delaware Pl, Chicago
4.1
of 5, from 2,123 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$143
Chicago's Essex Inn

Chicago's Essex Inn

800 S Michigan Ave, Chicago
3.6
of 5, from 1,356 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$159
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

5300 N River Rd, Rosemont
4.4
of 5, from 697 reviews
4.5 out of 5.0

This family-friendly Rosemont hotel is located near the airport, within a 10-minute walk of Rosemont Theatre, Fashion Outlets of Chicago, and Donald E. Stephens Convention Center. MB Financial Park at Rosemont and Rivers Casino are also within 2 mi (3 km).

C$162
Warwick Allerton Hotel Chicago

Warwick Allerton Hotel Chicago

701 North Michigan Avenue, Chicago
4.0
of 5, from 2,511 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$177
Hotel Felix Chicago

Hotel Felix Chicago

111 W Huron St, Chicago
4.0
of 5, from 1,319 reviews
4.0 out of 5.0

Hotel Felix Chicago is 5 blocks from the Magnificent Mile, one of America’s most dazzling thoroughfares. It’s a 7-minute cab ride to the Navy Pier Ferris Wheel, whose 40 gondolas command unmatched skyline and lake views. Chicago-Red Metro Station is a 6-minute walk from the hotel.

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