Chicago: beloved by Sinatra, home of the Playboy empire and shrouded in the mystery of Capone. Today, Chicago is every bit alive as at any point in our city’s legendary history.

Looking to paint this toddlin’ town red? Impress your FourSquare friends by checking into the newest and hottest spots in Chi-town:

Marilyn’s Chicago: Marilyn Monroe never lived in Chicago, but a tribute to the iconic bombshell seduces passersby from her perch on the Magnificent Mile. Flirty Marilyn has created quite a stir, but she isn’t the only new installation reviving the city’s glamorous heritage:

•The Pump Room: Once graced by Frank Sinatra and Elizabeth Taylor, the Pump Room is back on top of the Chicago scene. The reimagined Pump Room offers modern décor and a farm-to-table cuisine.

•The Trump Hotel: The newest addition to Chicago’s skyline offers three dining experiences, each with spectacular views, menus and cocktails. Hit up Rebar for happy hour; Sixteen for a special dinner and Terrace for a sexy date under the stars.

•The Bedford: This 1920s bank-turned-restaurant-and-lounge incorporates safety deposit boxes, teller gates and a one-ton vault door into its uber cool décor. Dining room serves upscale Midwestern fare and the party continues all night inside the bank’s original vault.

Which place is your favorite?