The Drake is the hotel of choice for visiting politicians and dignitaries. Winston Churchill, Pope John Paul II and Princess Diana all roomed at the 1920 landmark hotel, ideally located at the beginning of North Michigan Avenue. You may also recognize the Drake from its starring role in movies such as The Blues Brothers, Risky Business and My Best Friend’s Wedding. But this old star is losing its luster. While the public spaces still preserve the splendor of the past and some rooms got updated in early 2008, other guest rooms haven’t yet gotten their makeovers—and it shows. Avoid disappointment by asking for a newly renovated room (with gold and white linens and a flat-screen TV) instead of a not-so-luxe has-been.

The Drake Hotel Chicago Amenities:

• 535 rooms, 74 suites. High-speed Internet access. Restaurant, bar. Fitness center. Business center.