I wouldn't want to commute Winnetka-Des Plaines, and I'm not a fan of New Trier. (the top students are treated well, but the ones who struggle are pushed out- the admin is too concerned with keeping the average scores high, and don't want anyone who pulls down the curve. The students can be very clique-ish).

There are lots of Barringtons. Every town around there tries to get "Barrington" in the name or the postal code, so they can raise their property values. Some are more relaxed or low key than others. In general I think it's less pretentious than Winnetka.

There are some nice parts to Arlington Heights, and the train makes it easy to get into the city. Don't know how the schools are, but it's not a pretentious town.

Lincolnwood has very good schools, and is within commute distance. Look in the "Towers", the part West of the Edens Expy and south of Touhy- that's within in the budget range you mention.