[1] Windy City Times was founded in 1985 by Jeff McCourt, Bob Bearden, Drew Badanish and Tracy Baim, who started Sentury Publications to publish the paper.

Long-time writers include Rex Wockner, Yvonne Zipter, Bob Roehr, Richard Knight Jr., Jonathan Abarbanel.

[3] In 2017, journalist Gretchen Rachel Hammond was removed from her job after she published a story about three LGBT women who were expelled from a Gay Pride march for carrying a rainbow flag featuring a Jewish Star.

[7] The site has archived 70,000 articles from Windy City Times and other previous products including Nightspots—a biweekly, four-color, glossy entertainment guide—and Identity, a monthly online magazine.

Windy City Times is a member of the National Gay Newspaper Guild, and has received numerous honors for its work, both from journalism organizations and from the LGBT community.