State Street was immortalized by Frank Sinatra in his song “Chicago,” making sure people everywhere knew it was the place to be. As the city’s original main drag, a shopping outing with your friends on State Street is a true Chicago experience. It’s still home to a slew of resplendent, iconic old buildings and landmarks. Pay a visit to stores like the Old Navy flagship and Urban Outfitters. Make sure you leave ample time for a visit to the opulent Macy’s (formerly the beloved Marshall Field’s) to see this legendary building with its awe-inspiring glass ceiling crafted by Tiffany. The seventh floor food court is a fantastic place for indulging in the ever-desirable combination of astonishingly good food and enthralling people-watching. Time the end of your great day out for dusk when you can snap a group photo in front of the famous illuminated Chicago Theater sign to create a memory frozen in time. As Ol’ Blue Eyes said, you’ll have the time of your life.