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Chicago is also a convention town, so book your room well in advance:

bulletFour Seasons: the best hotel in Chicago; stunning lake view; pay the extra cash and get an executive suite ($$$$)
bulletRitz Carlton: operated by the Four Seasons; excellent rooms and a great lobby bar ($$$$)
bulletHotel Monaco: the funky place to stay; also more affordable ($$$)
bulletSutton Place: another "cool" hotel" however furnishings are a little stale ($$$)
bulletThe Raphael: the Grand Dame of boutique Chicago hotels; actually it blows...don't stay here.