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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.

For more details on interesting local attractions and activities, check out our things to do in Chicago page. 

Best time to visit Chicago

The ideal time to visit the Windy City is summer or fall. The summer months offer an endless selection of special events and outdoor activities, but also the biggest crowds and hot, muggy weather. However, autumn days are generally sunny, and the crowds are smaller at major tourist attractions. The first snow doesn’t appear until late November at the earliest. If you don’t mind being indoors, winter is a great time to visit. The weather may be blustery, but there are no lines at most attractions and the hotel rates are lower.

Peak season:A popular travel period is autumn (September–November), when the weather is moderate and the kids are back in school, making the city’s attractions less crowded. Spring and summer are also busy times. Spring weather can be unpredictable and summer can be warm; however, travelers enjoy endless special events.

Value season:If you’re looking for the cheapest hotel rates and don’t mind being indoors, travel between December and March. Added bonus: You won't have to wait to get into museums and other city attractions.

The Expedia Chicago hotels page contains no less than 165 upmarket and more affordable hotel and apartment options, so you shouldn't have any problems finding a great place in this highly popular destination.

If you and your travel companions are keen on finding a room or suite at the premier end of the scale, you'll be sure to enjoy the hospitality at The Peninsula Chicago, at 108 East Superior Street, or the Waldorf Astoria Chicago, at 11 E. Walton Street. Alternatively, the Old Chicago Inn, at 3222 N Sheffield Ave, and the Inn at Lincoln Park, at 601 West Diversey Parkway, are two value-for-money options that are sure to please.

If your time here is short and you'd like to stay close to the Art Institute of Chicago, The Langham, Chicago and the JW Marriott Chicago are both good options.


Guide to Exploring Chicago


Top Hotel Deals

See all 952 Hotels in Chicago
$143
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.4
of 5, from 387 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.

$130
Club Quarters Hotel, Central Loop

Club Quarters Hotel, Central Loop

111 West Adams Street, Chicago
4.2
of 5, from 2,042 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.

$191
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
4.2
of 5, from 2,556 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.

$169
The Whitehall Hotel

The Whitehall Hotel

105 E Delaware Pl, Chicago
4.1
of 5, from 2,116 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.

$116
Chicago's Essex Inn

Chicago's Essex Inn

800 S Michigan Ave, Chicago
3.6
of 5, from 1,351 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.

$129
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

5300 N River Rd, Rosemont
4.4
of 5, from 696 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).

$158
Warwick Allerton Hotel Chicago

Warwick Allerton Hotel Chicago

701 North Michigan Avenue, Chicago
4.0
of 5, from 2,508 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.

$134
Hotel Felix Chicago

Hotel Felix Chicago

111 W Huron St, Chicago
4.0
of 5, from 1,315 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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