Chicago, Illinois is the Midwest's most-visited metropolis, known around the world for its iconic skyscrapers, preserved Gilded Age mansions, and upscale Magnificent Mile shopping district. Friends traveling to the Windy City can explore delightful museums like Art Institute of Chicago or the historic Driehaus Museum, catch a Broadway in Chicago play at the Cadillac Palace Theater or the Broadway Playhouse, or take a spin on the city's massive observation wheel at the lively Navy Pier boardwalk complex. For a unique perspective on the city's architecture, the Chicago Architecture Foundation's Center River Cruises share stories on more than 50 of the city's most iconic buildings. The beautiful boutique-style Dana Hotel and Spa offers chic accommodations, a rooftop bar, and a full-service spa and sauna, great for posh weekend stays with groups of friends. Delicious dining destinations include elevated seafood joint Portsmith, Italian-style marketplace Eataly, and the rustic Dearborn Tavern.

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