It's Christmas Eve in rainy, icebound Wichita, Kansas, and this year Charlie (John Cusack) just might have something to celebrate. Charlie, an attorney for the sleazy businesses of Wichita, and his unsavory associate, the steely Vic Cavenaugh (Billy Bob Thornton), have just successfully embezzled $2,147,000 from Kansas City mob boss Bill Guerrard (Randy Quaid).
Even so, the real prize for Charlie would be the stunning Renata (Connie Nielsen), who runs the Sweet Cage strip club. Charlie's fondest Christmas wish is to slip out of town with Renata. But, as daylight fades and a storm whirls, everyone from Charlie's drinking buddy Pete Van Heuten (Oliver Platt) to the local police begin to wonder just what exactly is in Charlie's Christmas stocking. For Charlie, the 12 hours of Christmas Eve are filled with nonstop twists and turns, both on the ice and off.