This movie was filmed at the same time as Planes, Trains & Automobiles (1987), which was written and directed by John Hughes and The Great Outdoors (1988) which was written by him. Some of the same cast members from both films appear in this film.
Paul Gleason plays an uncredited character called "Blind Boy Grunt". Blind Boy Grunt was a pseudonym used by Bob Dylan in the early 1960s, and was also the name of a famous bootleg album of his in the early 1970s.
The company name of the Realtor on the sign of the home Jake and Kristi buy is Shermer. Shermer, Illinois was the town that The Breakfast Club (1985) was set in (another movie written and directed by John Hughes).