The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.

A short ride away from New York City on the Metro North commuter rail, Poughkeepsie sits on the banks of the Hudson River. The close proximity of Vassar College and the Culinary Institute of America guarantees the presence of fun boutiques and fine dining. Main Mall Row, a group of 1870s Renaissance Revival storefronts along Poughkeepsie's Main Street is on the National Register of Historic Places. The twenty-two surrounding parks provide the opportunity to take a relaxing break from city life.

Conquering New York in one visit is impossible. Instead, hit the must-sees – the Empire State Building, the Statue of Liberty, Central Park, the Metropolitan Museum of Art – and then explore off the beaten path with visits to The Cloisters or one of the city’s libraries. Indulge in the bohemian shops of the West Village or the fine dining of the Upper West Side. The bustling marketplace inside of Grand Central Station gives you a literal taste of the best the city has to offer.