It is possible to drive from Oak Park to Hyde Park reasonably quickly, if you take the Eisenhower to the Dan Ryan, and then drive across the South Side. For a variation, one could drive through the Loop and take Lake Shore Drive down to Hyde Park, but of course one would have to deal with the Loop traffic, then. Oak Park is about 25 minutes from the Loop in rush hour traffic, and I think Hyde Park would be reverse commute. Some don't like driving across the South Side slums, but I find them a beautiful part of Chicago, and the neighborhoods have moved up quite a bit. Transit from Oak Park to Hyde Park is pretty poor--one can take the el and then walk over to the metra line or wait for the bus, but toomanybooks has it right: transit is a trek.

Having grown up in Hyde Park and Oak Park, I can say they're fairly similar in overall feel. Oak Park is known for its architecture (Frank Lloyd Wright, Louis Sullivan, etc.), great schools, extensive libraries (a "village" of 55,000, the citizens recently voted to rebuild the main library, which project was just completed, and there are two branch libraries), park & rec system, and diversity. Under diversity, one can understand racial, ethnic, and class diversity, although the last has decreased a bit with the jump in housing prices over the last 10-15 years. Oak Park, as a largely residential suburb, has correspondingly high property taxes, in part because of its schools, libraries, and park system, and very limited industrial tax base.

Oak Park has the distinction of being the community at which the redlining and blockbusting that characterized late 1950s and 1960s real estate on Chicago's West Side were not allowed to dominate, and instead, an integrationist approach was taken. Although the reasons for demographic shifts on the West Side are many and complex, and people may find integration good or bad, that is only to say that within Oak Park there is a degree of pride in the community's diversity and open-mindedness, and that represents a change from the stereotypical Oak Park of Ernest Hemingway's youth or the 1950s (Hemingway, who grew up in Oak Park, famously referred to Oak Park as the land of "broad lawns and narrow minds."). Although there are a few pre-1900 farmhouses and other houses, most of Oak Park's housing stock is turn-of-the-century (ca. 1900s) or a bit newer, with the vast majority of the newest stuff having been built in the 50s, and quite a few condo projects (and the odd new home) in the last 10-15 years.

To get a feel for Oak Park, take a look at the Wednesday Journal, which is the local paper (http://wednesdayjournalonline.com/). One can also get the Oak Leaves, but that is more a mass-produced paper and won't give you the same perspective. I don't know if Bobbie Raymond is still around at the Oak Park Housing Center on South Blvd. near Austin (http://www.apartmentsoakpark.org/), but they do a good job of describing the village there and giving people advice on what the neighborhoods are in an even-handed way. They now offer an apartment listing service (i.e., different from what you're looking for), but call them up if you visit Oak Park with the intention of living there.

A couple drawbacks are that Oak Park is landlocked--so you don't get the lake views (or summertime lake cooling) you'd get in Hyde Park--and, while it has a nice park system (not to mention Jens Jensen's nearby Columbus Park in Chicago, with its recently restored refectory and waterfall, and the nearby Forest Preserve lands), it's not quite the same as the lakefront, Jackson Park lagoons, and Washington Park in Hyde Park. One has to go a little further for as much dog romping room.

More broadly, a challenge is that Hyde Park is also fairly isolated. A lot of what Chicago has to offer in terms of theater, music, and museums is closer to the Loop or towards the north side. While there is a sort of new neighborhood that has risen out of old industrial land just south of the Loop (I think Mayor Daley may have moved there), a lot of the more Hyde Park-like neighborhoods are north of Congress/the Eisenhower, and could require a commute across the Loop.

I'm not as familiar with what's towards the south. I think there are some great working-class neighborhoods down there, like Beverly or Pullman, but they have a bit more of a feeling of isolation from the rest of the city, or so I've heard.

If you are feeling adventurous, you might try buying a place around Garfield Park, in Austin, or on the South Side. These areas are still by-and-large slums, though, so although you might find an architecturally interesting house and large lot, the potential crime rate may be a bit different than what you're looking for. With the exception of magnet schools and some similar schools, the public schools in those areas are considered to be pretty bad.

-Hayden