I spent about 6 of our 10 years in Chicago in the back seat of a Cessna 172, 6 hours a day, 5 days a week. Filled in occasionally for the guy who was the "passenger" in the Jet Ranger. Not sure which was worse, cold weather or wind gusts over Lake Shore Drive. What really scared me was flying directly thru O'Hare airspace (over the tower) when I had chopper duty.
Easy work, but in hindsight 25 years later not one of my favorite experiences,