Rachael takes a neighborhood-by-neighborhood trip through Chicago. First stop is Andersonville, where Rachael tries the Swedish delights of Ann Sather. Rachael then tries her hand at the circus life by taking a class at the Gaonas Gym Flying Trapeze. After working up an appetite, Rachael zips over to Bucktown for a taste of Cuba at Cafe Laguardia. And when the sun goes down, Rachael heads to the Loop for Chicago history and Italian perfection at Gioco.