I'll add that while it's got a great transportation system, it's still a very car centric city.

Train transportation is directed at getting you into the loop, and not so great if you want to traverse to other parts of the city. Want to go from Pilsen to Lincoln Park? You'll probably drive. Pilsen to Wicker Park? I doubt you are going to take the bus, so you'll drive there too.

The advantage of it being flat is that you can cycle to those places, but that option doesn't work 4-5 months out of the year.