I write event previews for Flavorpill Chicago, a popular culture guide (ambiguous phrasing intentional). My latest night-out suggestion is here.
The Chicago edition is a satellite outpost of Flavorpill's New York HQ, a large, airy loft office in SoHo. I dropped by a few months ago and found it as virtually cool as the New York Times did. From time to time, Flavorpill transcends the virtual into actual coolness by not only writing about buzzworthy events but sponsoring them. At its latest throwdown, e.g., Kanye West rocked the mic.
If you live in Chicago, New York, Los Angeles, San Francisco, London or Miami (or frequent them, as so much of my jet-setting readership does), jump over to Flavorpill and check it out.