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.1987, Baim left Sentury Publications to found a new newspaper called Outlines. WCT and Outlines were the two primary LGBT newspapers in the region for more than 12 years. In 2000, Baim purchased WCT back from McCourt, and merged Outlines with Windy City Times. Baim is now Publisher and Executive Editor of Windy City Media Group. Andrew Davis is Managing Editor, Kirk Williamson is Art Director, Terri Klinsky is Assistant Publisher and Ripley Caine is Business Manager. Long-time writers include Rex Wockner, Yvonne Zipter, Bob Roehr, Richard Knight Jr., Jonathan Abarbanel. Director of New Media is Jean Albright. McCourt died in 2007.
Windy City Times is published weekly by Windy City Media Group, which also publishes Nightspots—a biweekly, four-color, glossy entertainment guide—and Identity, a monthly online magazine. WCMG also produces a twice-weekly podcast, Windy City Queercast, online videos, and a weekly e-newsletter.
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. Awards include from the National Lesbian and Gay Journalists Association, the Peter Lisagor Awards, and the Studs Terkel Award for Baim. Among groups honoring WCMG and Baim: Chicago Gay and Lesbian Hall of Fame; ACLU of Illinois; Human Rights Campaign; NOW; March on Washington Chicago Committee; Dignity/Chicago; Affinity; Greater Chicago Committee; Association of Latin Men in Action; and more.