Chicago Real Estate

Listings last updated 09/19/2021
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Chicago City Guide

Chicago is a bustling town with over 200 named residential neighborhoods. Some of those names are famous: The Loop in central Chicago, home to the main business district; Michigan Avenue’s fabulous Magnificent Mile; and the Gold Coast, which rivals Manhattan’s Upper East Side for stylish affluence. Chicago, today the largest city between the East and West coasts, was the destination of choice for Eastern European immigrants during the great wave of migration around the turn of the 20th century. Even today there are more people of Polish descent in Chicago than in any city other than Warsaw, and Chicago foodies are reaping the benefits with a bevy of Polish eateries spicing up a city known for its deep-dish, steakhouses, hot dogs and a growing molecular gastronomy movement.
  • Young Professionals
  • Culture
  • Excitement

Architecture and landmarks

Chicago rivals even New York City for its architectural pedigree. The skyscraper was invented here back in 1884 with the 10-story Home Insurance Building. While the original skyscraper has since been razed, the Rookery, an 1888 masterpiece from John Wellborn Root and Daniel Burnham, still stands as the world’s oldest skyscraper. Once the tallest building in the country, the Willis Tower (née Sears Tower) still reigns over the Chicago skyline as the second-tallest structure in the US. Chicago even birthed its own building trend – high-rises with orderly sets of windows are nowadays referred to as Chicago style. And famed architect Frank Lloyd Wright honed his Prairie Style in the Chicago suburb of Oak Park, giving Chicago the largest collection of Wright-designed buildings of any city in America.

Beloved Chicago landmarks include the flagship Marshall Field’s department store, the world’s largest in the 1890s, and the Merchandise Mart, the largest building of any kind when it opened in 1930. Illinois native and 16th president Abraham Lincoln is well-represented in Chicago - the Standing Lincoln in Lincoln Park on Dearborn Parkway is hailed as the finest portrait statue in the United States. The most recent president with Chicago ties, Barack Obama, has selected South Chicago for his upcoming presidential library. America's most iconic road, Route 66, begins its 2,448-mile odyssey to the Pacific Ocean on Lake Shore Drive in Chicago.

Architecture and landmarks

Real Estate Market

Real Estate Market

Chicago offers one of the densest housing markets in America with 271,493 condo units and 132,543 apartments. Co-ops are far scarcer, totaling 167 units. Homes include 269,960 properties of one story or more and 22,222 row houses. Chicago remains a hub of industry with 15,691 industrial properties and 16,299 mixed-use buildings. Business opportunities abound in the city’s 31,337 commercial properties and its 38,797 vacant lots.

The Cook County Land Bank Authority sells vacant lots for $1 through a dedicated program that had 4,451 vacant properties on offer in 2017.

Real Estate Market

Public services


Metra, the city’s passenger regional rail network, is the nation’s second busiest and O’Hare International Airport handles more flights than any in the world. The Chicago Transit Authority oversees an extensive elevated subway system –the famous “L” is the only one outside New York to operate round the clock. Chicago’s Divvy is North America’s largest bicycle sharing program by miles covered.


The Chicago Public Schools, with 600-plus elementary and secondary schools, are augmented by a bevy of parochial schools. Post-graduate opportunities abound, including the University of Chicago that was recently ranked #3 among all American colleges by U.S. News and World Reports.


Health care in Chicago is anchored by two celebrated academic medical centers, the Northwestern Memorial Hospital and the University of Chicago Medical Center. In recent years, the city's number of immediate care clinics outside of hospitals has doubled to 37.


Recent statistics show that the city has a higher average of violent crime, mostly attributed to gang violence, than other large American cities, but lower than average property crime rates.

Things to do

Things to do

Chicago has given rise to its own brand of blues, soul and jazz music, performed in many legendary venues, while the Shedd Aquarium, Adler Planetarium and Field Museum of History reign as cultural destination staples. Michigan Avenue is one of the world’s most fabled shopping destinations with over 200 restaurants and 400 retailers. The guided tours from the Chicago Architectural Foundation are must-dos for visitors and natives alike.

Things to do

For outdoor activities, the Lincoln Park Zoo is one of the last free-admission zoos in the country. Chicago is one of 12 American cities to host teams in all four major professional sports. Lake Michigan dishes up unlimited recreational opportunities on the water and on shore, where several parks and 24 public beaches make use of the waterfront.

Things to do

Lake Michigan’s Navy Pier with its family-friendly recreation area is the city’s biggest tourist attraction and a magnet for locals as well.