Hilton Chicago

When: Thu., Dec. 31, 9 p.m.-2 a.m. 2009

Outfit Events and Global Adrenaline host the official Playboy New Year's celebration, where general admission gets you an open bar, hors d’oeuvres, a buffet, "casino" gambling (till midnight), a champagne toast and confetti at midnight, plus performances by Pitbull and Jump Smokers. An extra $50 gets you a premium open bar, extended casino access, and a chance to party with the Playmates in the VIP lounge. Table reservations and packages are available for $1,000-$3,000.

Price: $155

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