Chicago Vacations

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Chicago Flight and Hotel Deals

The Willows Hotel
InterContinental Chicago Magnificent Mile, an IHG Hotel
Fairmont Chicago at Millennium Park
Best Western Grant Park Hotel
Royal Sonesta Chicago Downtown

Chicago Essential Information

Prepare for your Chicago vacation with our essential travel info

Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago

Chicago Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL, 60605
The price is $152 per night from Jun 7 to Jun 8
3.7/5 Good! (3,851 reviews)

Reviewed on May 17, 2022

Congress Plaza Hotel
21c Museum Hotel Chicago
21c Museum Hotel Chicago
4 out of 5
55 East Ontario Street, Chicago, IL, 60611
The price is $189 per night from May 30 to May 31
4.3/5 Excellent! (652 reviews)
"With one elevator down, it took almost 35 min for me to finally get a way to get downstairs. This was on multiple occasions. Was told by front desk you just have to wait. I think in this situation maybe opening up thr service elevator may have been considered, or at least signage on the broken ..."

Reviewed on May 16, 2022

21c Museum Hotel Chicago
Royal Sonesta Chicago Downtown
Royal Sonesta Chicago Downtown
4 out of 5
71 E Wacker Dr, Chicago, IL, 60601
The price is $229 per night from May 29 to May 30
4.2/5 Excellent! (1,819 reviews)
"Very good"

Reviewed on May 17, 2022

Royal Sonesta Chicago Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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.

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