The elegant Carbide and Carbon building, clad in black granite and gold leaf, has soared 38 stories over the Wabash River since 1929, and it's deservedly a landmark among Chicago's pre-Depression architectural masterpieces. The hotel inside goes to lengths to make sure its interior mood matches its exterior panache. Actually, the St. Jane (named for celebrated social worker Jane Addams) is more like two hotels. Stay in the St. Jane and you'll get a style that blends the dark elegance of Retro Deco style with fully modern amenities like top-line bathrooms and plush linens. (The walls can be a little thin, but that's any city for you, and rooms are decently sized, especially for a building of this age.) But if you stay in the Tower at St. Jane, which costs about a third more and takes up the slender skyscraper above, you get a much more memorable stay, including quieter rooms (there are only three on each floor), leather-and-black décor that accentuates the dark elegance of the building's Roaring Twenties profile, a private bar that's customized to your specifications, and an enviable view over the Wabash River and Michigan Avenue to make for years of good memories. The only way to get one of those Tower rooms is via the regular St. Jane hotel—it's not sold by outside websites. Overall, the service is excellent, quick-witted, and deeply attentive, and you'll find the upscale-contemporary, lobby-level restaurant (Free Rein) can proudly stand alongside any of the city's best tables. You will have no complaints about the location, either, at the nexus of Michigan Avenue's shops, the Loop's theatres, Millennium Park, and River North's watering holes. In many ways, it has an invitingly vigorous personality that only Chicago could produce.