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Among hundreds of Chicago non-traditional news sites, Windy City Times was ranked second according to a Chicago Community Trust report issued in June 2009. Windy City times ranked above web sites for NPR, the Chicago Reader and other independent and online-only media that were included.

Published since 1985, Windy City Times has won numerous awards from journalism prizes to community service awards:
- Crain’s Chicago Business 40 Under 40 for Publisher Tracy Baim.
- Peter Lisagor Chicago mainstream journalism.
- Q Syndicate national press awards.
- Community awards from a wide range of organizations, including The Human Rights Campaign, American Civil Liberties Union, National Organization for Women, Affinity, Dignity, March on Washington, Test Positive Aware, Bailiwick Theatre, and more.
- Studs Terkel 2005 Journalism Award for Publisher Tracy Baim