From its music scene to its museums, Chicago has a rich culture and history. Because the city is known as the birthplace of the American skyscraper, we recommend discovering the city through its architecture. Consider taking the architectural walking tour or a boat tour on Lake Michigan for a view of the skyline. The Museum of Contemporary Art, the DuSable Museum of African American History, and the Art Institute are not to miss, and don’t forget to cross Renzo Piano’s Nichols Bridgeway to see Millenium Park. We like the Peninsula Hotel for its classic elegance, as well as the Chicago Athletic Association Hotel, a fashionable hideaway. The city is home to a wide range of restaurants, but an exciting option is Alinea, which holds three Michelin stars. Head to the Chicago Symphony or Second City for nighttime fun.