Everyone wants the same thing in Chicago... two bedroom, two baths, parking, near the train, outdoor space, lots of light, near the lake, low assesment, storage and for $250,000, maybe $300,000. No problem!
When my clients come back to Earth, we try and figure out a few things that will really make living in the city... well... "living in the city".
My picks out of the above list? If you have a car, then you must have parking and outdoor space. Although, some neighborhood parking is not bad if you're a little west of the city. So, parking is a bit of a push.
If you don't have a car, outdoor space and transportation. If you have a great deck and can take the train or bus to all your destinations... you're city living.
If you are not worried about the outdoor space, and do not need parking... then you can get a much larger place. It's like a puzzle people.