This screenshot comes from The Break-Up, a 2006 romantic comedy co-starring Vince Vaughn and Jennifer Aniston. Here, we see Vaughn's character working as a tour guide on the Chicago River.
The Break-Up's screenwriter, along with Vaughn (a Chicago native), wanted to be sure Chicago was a star in the film as well:
"It was without question something the two made clear right from the get-go: they really wanted this film to not only look like Chicago but really, really embrace Chicago" (Chicago Tribune, 2006).
How do you think they did? 🤔