I've only had NY. I've had homemade soupy-looking pizzas before, but I can't say I ever had a true Chicago style pizza, so I'd like to try one at a restaurant sometime. Ever since I started cooking instead of my mom, I normally just make flat-bread pizza, and I'm yet to master hand tossing. I'd like to try a true Neapolitan pizza too. I like food, basically.
Both very different styles and both good. To me NY pizza is a light option for lunch or a snack and Chicago style is more dense and better for diner.