The Chicago Loop is probably the most important piece of Chicago real estate in the entire city. It is also the historic center of downtown Chicago and acts as the city's central business district, which is the second largest in the United States behind Midtown Manhattan's.

On the west and north, the Chicago River bounds the Chicago Loop and Lake Michigan bounds it on the east and on the south by Roosevelt Road. Typically, the term Chicago Loop refers to all Chicago real estate bounded by public transit along Lake Street on the north, Wabash Avenue on the east, Van Buren Street on the south, and Wells Street to the west. However, Chicago Loop is also used to encompass the whole business district and the Chicago real estate relevant to business.

However, "the Chicago Loop" does have more than one meaning. It can refer to all the Chicago real estate surrounded by the loop CTA circuit formed by the elevated train tracks. This "loop" also comes from the Chicago real estate surrounded by a streetcar loop in the 1880s. Usage of the term can also refer to all Chicago real estate bounded by the Chicago River on the north and west, the Congress Parkway to the south, and Columbus Drive to the east.

Officially, as delineated by the University of Chicago in the 1920s, the Chicago Loop is community area of Chicago number 32 and all the Chicago real estate bounded by the Chicago River to the north and west, Roosevelt Road to the south, and Lake Michigan to the east. The original boundary remains the Chicago real estate encircled by the elevated CTA track and the old streetcar loop.

Much of the confusion comes from downtown and its many chicago condos and high-rises, with business expanding out past the community area and encompassing more and more Chicago real estate and properties. In general, "Chicago Loop" has been used more and more frequently to mean the entire downtown Chicago area.

The neighborhoods included in the Chicago Loop currently are the Loop itself, New Eastside, Printer's Row, the South Loop, and the Historic Michigan Boulevard District.

In 2005, according to Forbes, the median sale price for residential Chicago real estate was $710,000.

The Chicago skyline, originating in the Chicago Loop, is appreciated all over the world with the Sears Tower, John Hancock Building, and upcoming Chicago Spire being notable parts of it. The LaSalle Bank Building is the former site of the Home Insurance Building, significant because it is considered the first skyscraper.

Additionally, the Chicago City Hall and Cook County Building, the James R. Thompson Center, the Richard J. Daly Center, and multiple other federal and government buildings are found in the Loop along with Chicago's Downtown Theatre District.

Along the lakefront, Grant Park houses Buckingham Fountain and the Petrillo Bandshell, and sits next to Millenium Park featuring the renown Cloud Gate sculpture. The Chicago River also cuts through the downtown Chicago area, providing much in the way of recreational and entertainment opportunities for both tourists and residents.