I noticed this again recently: the movie When Harry Met Sally gets an important feature of Chicago wrong early on. As described by IMDB:

When Harry and Sally drive from the University of Chicago to New York, they should drive on the Lake Shore Drive heading to the south (to the direction of Gary), not to the north (to the direction of downtown). So they should not be on the Lake Shore drive on the north of downtown.

It is not clear how this mistake was made but it could be an easy one to make for multiple reasons:

1. The University of Chicago is an island onto itself on the south side of Chicago. It takes several miles and multiple social worlds to get to the better known, wealthier, whiter part of Chicago (the Loop and North Side). Perhaps this is commentary about where University of Chicago students end up?
2. Would the view along the southern portion of Lake Shore Drive be recognizable to many people? The views of Chicago are very different at these different ends. The southern approach to the city provides a more industrial, working-class view while the north side emphasizes high-rises and waterfront amenities.
3. Perhaps this could further fuel Chicago’s sense of inferiority compared to New York City: “they don’t even know the north and south sides of our great city!”