Chicago Midway International Airport, typically referred to as Midway Airport, Chicago Midway, or simply Midway, is a major commercial airport on the Southwest side of Chicago, Illinois, located approximately 12 miles (19 km) from the city's Loop business district. Established in 1927, Midway served as Chicago's primary airport until the opening of O'Hare International Airport in 1944. Today, Midway is one of the busiest airports in the nation and the second-busiest airport both in the Chicago metropolitan area and the state of Illinois, serving 22,050,489 passengers in 2023.

Chicago O'Hare International Airport is a major international airport serving Chicago, Illinois, located on the city's Northwest Side, approximately 17 miles (27 km) northwest of the Loop business district. Operated by the Chicago Department of Aviation and covering 7,627 acres (3,087 ha), O'Hare has non-stop flights to 214 destinations in North America, South America, the Caribbean, Europe, Africa, Asia, the Middle East, Oceania, and the North Atlantic region as of November 2022. As of 2023, O'Hare is considered the world's most connected airport. It is also U.S.A.'s 4th busiest airport, and 7th biggest airport.