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Chicago boasts many upscale neighborhoods, but none more historic and prestigious than the Gold Coast. Railroad, retail, and lumber tycoons built this elegant district in the decades following the Great Fire of 1871 (see 1871: Great Chicago Fire), and its leafy streets are lined with 19th-century mansions interspersed with early 20th-century apartment buildings. There are no less than 300 designated historic landmarks in the Astor Street District alone, including buildings by Stanford White (such as 20 E. Burton Place), and Charnley House, designed by Louis Sullivan (assisted at the time by Frank Lloyd Wright). (1365 N. Astor Street).

This 1873 town house makes a pleasant change from the large hotels, with just four individually decorated rooms. Guests are welcome to use the comfortable sitting room and ivy-walled garden.

One of Chicago’s leading theater companies, the Goodman frequently spins off productions to Broadway in New York and has earned a Tony award, the theater community’s highest, for its efforts. Noted productions include dramas by Eugene O’Neill and August Wilson and an annual version of Charles Dickens’ A Christmas Carol .

This slick Northside jazz club offers some of the city’s best sightlines. Named for a jazz standard, Green Dolphin encompasses both a separate fine dining restaurant and an equally spacious showroom that also serves casual café fare. On the musical bill expect the sorts of ensembles that can audibly fill the space, such as big bands and Latin groups.

This centrally located, family-friendly hotel offers two-room suites – with fully equipped kitchens – as well as many standard guest rooms. Bonuses include the fitness facility, indoor pool, complimentary breakfast buffet, and daily newspaper.

This extravagant 381-room, musically themed hotel occupies the former Carbide and Carbon building – an Art Deco creation of 1929. Piped music and memorabilia are everywhere, and rooms are stylish but fun.

Named after former city Mayor Harold Washington, Chicago’s first Afro-American mayor (see 1983: Harold Washington elected Mayor), this is the largest public library building in the country. Its collections, which include a superlative Blues Archive and a vast children’s library, fill an incredible 70 miles (110 km) of shelving. Architects Hammond, Beeby, and Babka incorporated architectural elements of several Chicago landmarks, such as The Rookery and The Art Institute (see The Art Institute of Chicago) in the building’s design: don’t miss the ninth-floor Winter Garden atrium, which soars two stories to a spectacular glass dome.