Celebrity Hotel Hookups

THE LOVE NEST: Four Seasons, Chicago

THE PLAYERS: Jennifer Aniston and Vince Vaughn (and John Mayer)

THE DISH: While filming The Breakup in Chicago, Jennifer Aniston and Vince Vaughn did precisely the opposite of what their characters did: They got together. Despite denials—Vaughn noted that her then recent split from husband Brad Pitt made Aniston too "vulnerable" to date—the couple were consistently spotted frolicking in parks, dining out together, and smooching in public. Eventually Aniston was seen stealthily scurrying out of Vaughn's digs at the Four Seasons Chicago in the wee hours of the morning, hoping to return to her suite at the nearby Peninsula undetected (obviously not so successfully, as evidenced by stories in Britain's News of the World and several other newspapers). On later trips back to the Windy City (which is Vaughn's hometown), they were less cagey, checking into the Peninsula together in October of 2005, where they were seen making out on their suite's balcony and working out together in the gym. Since then, Aniston has moved on to other, less pudgy celebrity men—and other hotels. Some months ago, she and former Jessica Simpson–romancer John Mayer holed up at the Mandarin Oriental in Miami, where they were caught canoodling in the pool and where, according to Us Weekly, John sent flowers to Jen in their room multiple times during their hot-and-heavy five-day stay.

NEXT: Love in an elevator >

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Information may have changed since date of publication. Please confirm details with individual establishments before planning your trip.

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