A bickering couple (Vince Vaughn and Jennifer Aniston) live in a wonderful condo in Chicago. Both driven in their careers with Gary (Vaughn), a Poland-loving man running a thriving city tour business with his brothers (Vincent D'Onofrio and Cole Hauser), while Brooke (Aniston) works as a representative for her boss' (Judy Davis) art gallery. Early in the movie, their conflicts cause them to separate after a bitter argument. Although Gary believes he's fighting for the condo, it's Brooke who is fighting for their relationship to stay alive. However, the condo ends up becoming the subject of a war in which both try to outwit and outdo each other through blind dates, obnoxious parties and broken promises. In the end, both mutually agree to separate, selling the condo; Gary continues to run his business which is booming while Brooke (Aniston) travels the world, eventually finding her way back to Chicago. At the end of the movie, they meet again on the streets of Chicago uneventfully. After some words, they part ways, glancing at one another while smiling.