While observing the practice of one of the bands, Emily is eating fruit. She is waving around a piece of melon and it suddenly turns into a grape.
At the end of the film as Emily climbs up on the Christmas float to talk to Henry she removes her headset twice.
When Emily and Henry are walking to lunch, Henry's tie starts out gray but by the time they arrive at the restaurant, it is black and striped.
When Henry finally gets Emily on board the charter taxi, the taxi is white and blue. When the charter taxi is shown floating in the next scene, it's yellow.
In the split screen the night before the parade, Emily is shown sleeping in a top with spaghetti straps and bare arms. When she is shown waking up the next morning she is shown in bed in a different outfit where her top has full lace sleeves.
When Emily shows Henry the picture of her dad at the pizza place, his hat is plain black. The Chicago PD has had Sillitoe tartan (checkered) hat bands since the 1930s.
Henry talks about going to a 4-star rated Michelin restaurant and alludes to another 5-star restaurant that is closed. However, Michelin only rates restaurants on a 0- to 3-star scale.
When Emily goes to Jim's Pizza, her favorite Chicago haunt since childhood, the phone number 467-6931 is prominently displayed on the outside awning. But Jim's Pizza is actually located in Maple Ridge, British Columbia and still has that very same phone number.
Emily states that she wears vintage clothes from the 1950s and early 1960s in the hope that perhaps she may wear something that belonged to her mother, whose clothes were given away by Emily's father following her passing. Assuming the story takes place in current day (that assumption strengthened by the character of Henry, portrayed by Antonio Cupo, being born in 1978, Cupo also born in 1978), it is more likely that Emily's mother's "adult" clothes would have been from the 1970s and not the 1950s.