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Also known as Tufano’s, this popular bar counts legions of local and celebrity fans who pile in for house wine and generous, inexpensive pastas.

This hotel is trendy yet traditional, with comfy couches and board games in the lobby. Guest room decor is inspired by 1940s Hollywood glamor, with chaises longues and ostrich-leather headboards.

A Zen water wall and “Leave me alone”, rather than “Do not disturb” signs are indications of the W’s hipper take on the hotel experience. The modern guest rooms have lovely views, as does the rooftop lounge, Whiskey Sky.

Another Prairie–style architect (1876–1937) with a namesake historic district on Chicago’s Southside.

Frederick Law Olmsted and Calvert Vaux, the designers of New York’s Central Park, also created this 371-acre (150-ha) green space for Chicago residents in the early 1870s. It originally attracted mainly wealthy city dwellers who enjoyed parading around the scenic space. Today, it’s a beautiful and widely used park with recreational programs, the DuSable Museum of African-American History, and Lorado Taft’s striking 110-ft (34-m) long sculpture, Fountain of Time , which took him 14 years to build. It is unwise to venture into the park after dark.

Opposite the historic Newberry Library, Washington Square is a prime plot of Gold Coast for resting tired feet and gazing at the handsome 1892 building. The park’s ample benches tend to draw bookish sorts and picnicking office workers at lunchtime.

Level 3 of this tony Michigan Avenue mall is primarily devoted to children’s retailers including clothiers Oilily Children, Benetton Kids, The Children’s Place, and Hello Kitty! specialist, Sanrio. Across the hall from the Lego store, the Lego Construction Zone sets out Lego bricks for play. The fourth floor food court sells kid-favored foods like hot dogs and pizza.

This sleek, four-star venue is home to a state-of-the art Executive Business Center, fitness facility, and guest rooms featuring the ultra-comfortable Westin Heavenly Bed.

An immaculate 11-room hotel, this 130-year-old mansion is known for its great attention to detail. Soak up the lavish artwork, period features, and antique furniture, or take it easy in the tranquil garden.

Run by Rande Gerber, husband of supermodel Cindy Crawford, this sophisticated, sleek bar attracts a trendy crowd.