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One of the biggest cities in the US, Chicago, Illinois on Lake Michigan is famed for its skyline of skyscrapers. The city is well known for its museums, notably the Art Institute of Chicago, which is home to notable Impressionist and Post-Impressionist pieces. There are more things to do in Chicago than you can possibly do in a single visit. With a population of over 2.7 million, Chicago is the third-largest city in the United States and the biggest in the Midwest. Get Cheap Flights from Chicago to both Domestic and International Destinations.