One night stay in a Deluxe King Room at the Kimpton Gray Hotel, Chicago, Illinois.

Situated in the historic New York Life Insurance Building originally built in 1894, The Kimpton Gray Hotel takes its name from the Georgia Gray marble that’s lent the structure a sense of sophistication for well over a century. The ornate architecture on the granite exterior and in the lobby — with Art Deco light fixtures — is juxtaposed against contemporary-styled rooms with crisp furnishings.

Here in the Financial District, the neighborhood buzzes during the 9-to-5 workday and hosts chic city dwellers in the evening — which is just the time to visit our on-site, in-the-know hangouts: Vol. 39, a sophisticated lobby bar with wine, champagne and caviar, and Boleo, the top-of-the hotel bar and lounge with retractable roof.