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GOOD FOR: Your upper-crust mother-in-law, decked out in pearls and couture
WHERE: Elysian (11 E. Walton St.; 312-646-1300, elysianhotels.com). From $385.
THE GIST: With only ten rooms per floor, this hotel feels more like a high-end condominium. The fireplaces and in-mirror TVs in almost every room and 1920s–Paris–inspired décor only add to the niceties.
INSIDER TIP: A complimentary courtesy car takes guests anywhere within a two-mile radius.
SCENE AT THE BAR: With its deep leather chairs, Bernard’s Bar could be an exclusive gentlemen’s clubhouse, but drinks like the Aviation—with gin and crème de violette ($14)—are female friendly.