[1] It was founded by John A. McDermott, who sought to create "the nation's first publication devoted to analyzing and investigating local racial issues.

The paper's earliest influence was its expose of the Chicago Police Department's discriminatory disorderly conduct arrests in 1982,[4] which prompted the American Civil Liberties Union (ACLU) to file suit against them, leading to a U.S. District Court Judge to rule their arrests unconstitutional.

[5] In 2007, The Chicago Reporter also released a study detailing how the largest mortgage lender in the country, Countrywide, was lending high interest loans in majority to minority lenders leading then attorney general of Illinois Lisa Madigan to subpoena Countrywide, ultimately resulting in an $8.7 billion settlement in 2008.

[2] The Chicago Reporter's style is regarded as "dispassionate investigative journalism" that has garnered it critical acclaim by several other news publications as well as politicians.

In a digital world of speed and brevity, their coverage takes the time and invests the analysis in issues ranging from gun control to deficits to immigration.