I think either Wednesday or Saturday I am going to take a 2012 prius 2 out for a test drive and see how it goes.
I don't think anyone asked this yet so, "do you plan to stay living in downtown Chicago for more than 5 years?" That is something I'd consider as well. So that your purchase isn't only limited to the now...but also the later. Assuming you won't want to purchase another vehicle in a short amount of time. Most of my drives are short trips to the grocery store, which is less than 2 miles away, in the far NW suburbs of Chicago. I also make jaunts of about 7 miles to the nearest larger town for shopping. I still average from 48/52 mpg while driving in normal mode and not doing anything else special. Winter driving will drop the average down some, I don't have winter tires, and believe the Prius does an excellent job in snow. If you enjoy your test drive, then I'd say go for it! Get what you want and enjoy it while you can!
I don't live in dowtown and actually don't work in the loop either. but yes 4th gen Chicagoan and don't plan on changing that for my kids (5th gen) either. The goal is if I buy the prius I will drive it into the ground. Well that was my goal with the Sonata too