Chicago Vacations

Chicago Flight and Hotel Deals

Hyatt Regency Chicago
Hyatt Centric Chicago Magnificent Mile
Extended Stay America Suites Chicago O'Hare
The Chicago Hotel Collection River North
Red Roof Inn PLUS+ Chicago - Naperville

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

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL, 60611
The price is ¥19,603 per night from Jul 18 to Jul 19
3.8/5 Good! (1,572 reviews)
"It was unfortunate that they had no breakfast service. However, they were able to direct us to a good place to get breakfast nearby."

Reviewed on Jun 24, 2022

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL, 60605
The price is ¥20,583 per night from Jul 4 to Jul 5
3.7/5 Good! (3,784 reviews)
"All I can say is that it was nice hotel and there's nothing bad to list off about it."

Reviewed on Jun 28, 2022

Congress Plaza Hotel
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL, 60605
The price is ¥21,645 per night from Jul 5 to Jul 6
3.2/5 (1,147 reviews)
"If you are looking for an affordable hotel at a convenient walking distance from Grant Park, Soldier Field, and Museum Campus, this is it. The Thai Spoon and Sushi is adjacent to the hotel, and there is also a Baskin-Robbins, Himalayan Restaurant, Subway, and Harolds Chicken Shack directly across ..."

Reviewed on Jun 27, 2022

Travelodge by Wyndham Downtown Chicago
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.

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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