Vince and Jean moved from the burbs to downtown Chicago after their son left for college. But their one bedroom condo isn't big enough for his regular return visits, so they're ready to upgrade to something with more space. Unfortunately Vince is dead set on lake views, and Jean is all about the Chicago skyline.
Alex and Anthony live in a 300 sq. ft. apartment in New York City, but they've decided that they'd like to start a family, so they'll need more space. Since they have a limited budget, they're targeting larger, more affordable condominiums in nearby Jersey City. Anthony, a flight attendant, is looking for a pre-war building, which he feels has the charm and character he has seen through his travels. Alex is an engineer who would like to find a sleek, modern, luxury high-rise with city views. Will these New Yorkers be able to compromise so they can become Jersey Boys?