Hilton Chicago

When: Fri., Dec. 31, 9 p.m.-2 a.m. 2010

General admission at the official Playboy New Year's celebration gets you a four-hour open bar, hors d'oeuvres and a buffet, a midnight toast, and a performance by rapper T-Pain. The VIP option adds an extra hour of free drinking, more food, casino-style gambling, and a meet-and-greet with eight Playboy playmates.

Price: $165-$215

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