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I lived on the south side for 5 years while attending college at UofC. I like Hyde Park/South Kenwood a lot. Certainly an elegant neighborhood with an intellectual character by virtue of UofC's presence. There are other benefits: the park on Promontory Point is wonderful--like parts of Lincoln Park but without the overcrowding in the summer. However, its certainly not vibrant like Lincoln Park or other parts of the North side. And another negative is the grocery stores--no Whole Foods or Dominicks or even a Jewel, only two neighborhood groceries which, despite being technically owned by their customer base (its a co-op) do not, in my opinion, serve customers very well. For a good grocery store with good prices, variety and produce that is actually fresh, you have to drive west to Cub Foods on the city border, or up north to the new grocery stores on Roosevelt.

Your neighborhood requirements seem to be low, so maybe Hyde Park would do the trick. The prices per square foot are certainly lower than downtown or North Side, and commuting to the Loop is relatively easy if you're near the Metra stop. (If not though, taking the 55 bus to the Red Line is drag, and coming home that way late at night, if it can be avoided, should be!)

For me, an urban neighborhood has to have a good movie theater that is within walking distance, and Hyde Park was so-so on that account. When I was there, the neighborhood lacked a good movie theater with the exception of Doc Films, the university's wonderful student-run theater showing unusual/foreign films on weeknights and second-run blockbusters on weekends. The Hyde Park theater on 53rd was extremely run down and rarely played movies I wanted to watch. There was talk of a multiplex replacement for the Hyde Park theater several years ago, but I don't know if that ever took off.

As to crime reportage, the crime rates in south side must be higher than in the north side--especially surrounding Hyde Park. Hyde Park is bordered on three sides by neighborhoods (or the remains of neighborhoods) that are terrible. The murder rate along 55/Garfield itself was high enough that some cab drivers refused to drive down that road. You can claim that this is overreacting, and I think you would be right -- I rode my bike through some of these neighborhoods without incident, but the psychic costs of crime are high even for those who never experience it themselves.

As to highrises along the southern lakefront: they do exist but some are farther from the lake. Just south of McCormick Place is the landscaped "Prairie Shores" -- one of the few examples of "towers in a park" concept in the city that is market rate, not public.
 

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I'm surprised that the zip code that appears to include parts of the Loop is in the lowest income bracket. I suppose this reflects the lfact that very few people lived in this area, especially "back in 1999" except for people in South Loop SROs? I wonder whether continued interest in the central area by people with money will make appreciable differences in maps like these. Which expansion of the red will happen first?
 
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