The area is completely different. You might as well be looking in Cicero or Chicago. Oak Park has wonderful schools and wonderful homes regardless of where you are in Oak Park. If you want ALL the positive aspects and few of the negative aspects of Oak Park, you want to be North of Chicago Ave and West of Ridgeland.
Ridgeland is the East/West dividing line because the East side can be 10' lower in elevations. The lots are smaller and basements often have water problems. The North/South dividing line isn't as clear-cut but it is further North than 290, either Lake St or Chicago Ave.
Oak Park, IL is nationally known for its acceptance of diversity (along with Evanston, IL). At my open houses (on the West side of Ridgeland Ave) about half the couples/families looking were mixed races. It is almost comical looking at the demographics because it is tooo perfectly diverse. Here is an example:
Group #1) White husband, black wife
Group #2) Black husband, white wife
Group #3) Gay couple
Group #4) White family, 2.3 kids
Group #5) Black family, 2.3 kids
Group #6) Asian family
Group #7) White couple with grandma and 2 adopted black children
Personally, I think children will learn more at Hatch Grade School than the overly touted Mann School. I think all the OOOHHH MANN the best scores!!! is really the reason agents get in trouble all across the country for telling you one school or area is better than another. It's a veil of discrimination. Yes, the test scores are higher at Mann but so is the white population. It has NOTHING to do with whites being smarter but it has to do with money is power and subtle discrimination. Hatch has more diversification and SMALLER class sizes.
I grew up in a small white town in Michigan. There was no racism or discrimination because there was no one to discriminate against. When I went to Michigan State Univ, I got culture shock. I didn't see my roommate as black, I saw her as a person. But what a different life and culture she grew up with! I had no idea?! I could tell you a bunch of stories, but the point is, a child will learn more and do better in life if they are exposed to experiences beyond their own.
I think I answered your question specifically, probably too specifically. My summary Point Of View is like Goldilocks: South of 290 is too hard, expensive North West area is too soft, (shameless self promotion now) 1205 N Ridgeland is just right!
Feel free to contact me for additional perspectives of the area.
P.S. My first home was in Cicero. One of my soap-boxes is labeled Discrimination in Cicero. You don't want me to stand on that one, it's hard to get me down.