Often called the Second City -- not because it's second-class, but rather because it was entirely rebuilt in 1871, when the Great Chicago Fire destroyed a third of the city -- Chicago is second to none when it comes to fun things to see, do, eat and experience. A city of neighborhoods, Chicago has something for everyone, from the Cubs-crazed Wrigleyville on its North Side to President Barack Obama's stomping grounds in Hyde Park on its South Side. No matter what you want to see, or where you want to go, the city's famous elevated train, the "L," can take you there. Want to shop? Take it to the Fifth Avenue of the Midwest, Michigan Avenue, a.k.a. the Magnificent Mile. Into architecture? Take it to the Chicago River for an architectural boat tour, or to the western suburb of Oak Park, which is home to a smattering of buildings by Prairie-style architect Frank Lloyd Wright. Hungry? Take it to any one of the city's more than 6,000 restaurants.

The train is convenient, but walking in the Windy City is just as easy. If you've got strong legs, let them take you on a stroll through Millennium Park or along Chicago's gorgeous lakefront, where the oceanic Lake Michigan is dressed up with miles of bike paths and beaches. After that, take a walking tour of downtown Chicago, where you'll see a slew of iconic Chicago sites, including the Chicago Theatre on State Street, famous for its classic marquee; Navy Pier, with its signature Ferris wheel; the Art Institute of Chicago, which is home to famous paintings like Grant Wood's American Gothic and Andy Warhol's Mao; and two of the country's tallest buildings, the 108-story Sears Tower and the 100-story John Hancock Center. Take it from VIP locals like Oprah Winfrey and Michael Jordon, who'd no doubt agree with Frank Sinatra's famous lyrics, "Bet your bottom dollar you'll lose the blues in Chicago."