OK, so it’s not a video. It’s a movie clip. But I’m in Chicago for business, staying at the corner of Madison and Wabash, and I had to share something appropriate. I tried to think of Chicago-themed videos, but I could come up with was 1) songs sung by Chicago, and “Stay the Night” will likely be featured here someday; and 2) John Hughes movies.
But really, most teen movies in Chicago occurred in the suburbs, with occasional excursions into Big Scary Downtown, or Big Scary South Side. This movie was no different, except traveling into Big Scary Downtown was actually what the entire movie was about: stealing mom’s car, running away from home, clinging to the side of a building, Elisabeth Shue, and a slightly embarrassing, completely gratuitous musical number: this is what hijinks were all about.
P.S. If I remember correctly, my sister promptly asked for a wool duster and long scarf after the movie came out. I wonder if the few true geeks that lived in the 80s thought she was emulating the Fourth Doctor.
slumber party movies 
This is the best bored, yet easily-impressed blues audience in slumber party movie history. Kudos to casting.
PS: I want to see a picture of your sister in that coat and scarf. That must have been bad ass.