The Cheekiest Chicks of 2013! January 16, 2013 Hey it's Cheeky Jessica! We're serving up another swank event for you! The true essence of being Cheeky is all about confident women treating each other with respect. As a women’s lifestyle magazine in the city, CheekyChicago is honoring, empowering and celebrating ten of the most successful, powerful women in Chicago, while sharing the true meaning of living the Cheeky way, every day.