Park Grill

If you don't mind mingling with the masses of tourists yearround, then go for it. Millennium Park's award-winning restaurant serves contemporary American cuisine, and even though there's nothing ground-breaking about the menu, this spot stays crowded. Perhaps it's because of the sweeping views of the city, live entertainment and ice skating rink come winter. Or maybe it's their outdoor cafe that's so appealing: the city's largest alfresco dining with live entertainment nightly.