Search over 1 million properties and 550 airlines worldwide
Search over 1 million flights, hotels, packages, and more
Free cancellation on most hotels. Because flexibility matters.
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
4.5/5Wonderful!(93 area reviews)
Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.
5/5Exceptional!(4 area reviews)
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
4/5Very Good!(1 area review)
South Loop is the place to go for jazz and blues, museums and some of the hottest new pubs and restaurants in town.
Travelers to Chicago give high marks for the popular theater scene, interesting architecture, and renowned art. Vibrant and scenic, this city will delight tourists with its monuments, museums, and entertainment choices. Top sights in the city include Millennium Park, Willis Tower, and Skydeck Ledge.
Known for its theaters, art, and museums, the city's cultural venues include Chicago Cultural Center, Ford Center for the Performing Arts Oriental Theatre, and Chicago Theatre. Attractions like Skydeck Ledge, Six Flags Great America, and Navy Pier are fun for kids of all ages. The city is notable for its monuments and landmarks like Willis Tower, John Hancock Center, and Buckingham Fountain.
In Chicago, there are 995 hotels and other lodging accommodations so you'll have ample places to choose from for a perfect vacation. Below are highly ranked ones based on our user reviews:
Other favorite sights in Chicago include Millennium Park, McCormick Place, and Wrigley Field.
With so many transportation options, exploring Chicago is a breeze. Take advantage of metro transit at Monroe Station, Monroe Station, and Adams-Wabash Station. If you want to journey outside of the city, ride aboard a train from Millennium Station, Chicago Van Buren Street Station, or Chicago Union Station.