Originally Posted by ElmhurstNick
I grew up in Wilmette and went to New Trier, and think it was an excellent foundation, but the commute will kill you. The commute south of North Avenue such as Hinsdale (where $900k might not be enough) or Clarendon Hills (excellent suburb, many parts have Hinsdale Central high school) will also kill you if you want to keep it to 30 minutes. And I'd say that the same would apply to anything in traditional Barrington along IL 59, as I-90 is a general mess most mornings.
My gut instinct would be to look at the Glenbrook South, Deerfield, and maybe Maine West and Glenbrook North high school districts. My cousin and his wife (both physicians) had a similar commuting situation as you are describing and picked Deerfield.
But if education is your top priority, focus on the high school districts first, then the K-8 districts within the high school district, then the neighborhoods.
Ole Nick clearly knows what he's talking about. Forget Winnetka or any of the North Shore suburbs - not b/c of the snob factor but because of the distance. They're absolutely unworkable. Frankly, if you're trying to achieve a truly good/reasonable commute, I would draw a circle roughly 4-5 miles around Des Plaines and discount anything around it.
For what it's worth, I think the best balance you're going to find in terms of 'nice' area, really good schools, and ease of access/distance is going to be the Glenview area, as suggested.