Most Overrated Hotel: The Palmer House Hilton was once the grande dame of elegant Chicago hotels, but its glittering lobby is the only remnant of that past. Now it's basically a gathering place for conventioneers. Stay here only if you get a good rate -- but don't expect anything special.
Most Overrated Restaurants: The Cape Cod Room and the Pump Room are two venerable old restaurants in venerable old hotels (The Drake and the Omni Ambassador East, respectively). Chicagoans who have been dining there for years have a soft spot for these places -- understandably -- but they don't offer visitors any dishes that can't be found at dozens of other places -- for much more reasonable prices.
Most Overrated Entertainment: Steppenwolf Theatre Company deserves much of the credit for making Chicago a thriving theater town. Its in-your-face performances in the 1970s and 1980s -- featuring future stars such as John Malkovich and Gary Sinise -- were truly revolutionary. Going to see a Steppenwolf show meant a guaranteed thrill ride on an emotional roller coaster. Alas, the actors that gave Steppenwolf its edge are now focusing on their movie careers. Although names such as Sinise, Malkovich, Joan Allen, and John Mahoney are still listed as part of the Steppenwolf "company," they hardly ever appear on stage. Steppenwolf's productions are now a combination of new works and imports from New York, some impressive, some so-so. But hardly revolutionary.
Most Overrated Attraction: The view is stunning from the Sears Tower Skydeck -- once you finally get there. But long lines and crushed-together crowds can make you feel as if you're ready to hit the road by the time you finally reach the top. You'll enjoy the same vistas from the top of the John Hancock Building, which is usually less crowded and in a more tourist-friendly location.
Most Overrated Store: When it opened, Niketown was something new, a sports-as-entertainment retail complex. Now it no longer feels so fresh; it's really just another sporting goods store with a more limited selection than most -- a fact that doesn't stop the crowds from streaming in.