Many celebs have checked into this Gold Coast hotel, including Vince Vaughn, Richard Gere and Frank Sinatra (who has a celebrity suite named after him). One reason for its popularity is its location. The hotel sits among residential buildings in a tony neighborhood, plus it’s near the jogging trail and volleyball courts of Oak Street Beach. Another reason may be the famed Pump Room restaurant, where Old Hollywood stars flocked to its fabled Booth One, a table that only the most exclusive diners could snag. Robert Wagner and Natalie Wood toasted their wedding in that booth, as did Lauren Bacall and Humphrey Bogart when they got hitched. Frequent guest Judy Garland even paid tribute to the hot spot in her song Chicago: “Chicago, we’ll meet at the Pump Room, Ambassador East.” If you meet at the Pump Room today, you’ll feast on contemporary American cuisine from executive chef Nick Sutton.

The Ambassador East Hotel Amenities:

• 285 rooms. Wireless Internet access. Restaurant, bar. Fitness center. Business center.