The food fight that starts between a few people and ends up involving the whole crowd, is reminiscence of the action in William Shakespeare's Romeo and Juliet Act 1 Scene 1.
"The Chicago Way", as immortalized in the famous scene from Brian De Palma's 1987 film The Untouchables, is a tactic of using an exaggerated sequence of violent escalations to gain the upper hand on your adversary. "The Kerkovich Way" involves supporting a false story by escalating to more and more desperate heights to keep up the lie. Aside from the many references to the Chicago-based films of John Hughes connected to the scavenger hunt part of the storyline, the baby carriage scene from The Untouchables was clued in the final race stage.
When Jane mentions that she married Brad because of her vision board, Brad says "Technically, she didn't have me on the board, it was just a picture of one of the guys from In Living Color." In Living Color was an early 90's sketch comedy show that starred the Wayans brothers, including Damon Wayans, Sr., the father of the actor who plays Brad.
Max: I totally thought I was gonna be putting the lotion in the basket...
Max is referencing a scene in the 1991 film The Silence of the Lambs. Serial killer Jame 'Buffalo Bill' Gumb repeatedly tells captive Catherine Martin to put (or place) "the lotion in the basket" that he has lowered down into the pit where he is keeping her.