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.
I'd say it's car centric depending on where you live. I designed my life around being able to walk everywhere I need to or hop on the CTA to get places I cant walk. But I'm in a rare part of the city where I can walk to the red line or blue line in 5ish minutes. If you live elsewhere, or cant afford to uber from time to time, a car would be a big plus.
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.