Located just north of The Loop, Gold Coast is one of Chicago’s most affluent and popular neighborhoods. The original Playboy, Hugh Hefner, once had a mansion here. In addition to prestigious hotels, historic mansions and luxury high-rise apartments, you’ll also find upscale specialty boutiques and Michelin-starred restaurants. Walk along Oak Street for your shopping fix and dance through the night along Rush Street. The Newberry Library is also a great stop to check out noteworthy exhibits and rare book collections.