R.S.
Skokie sounds like the perfect solution for you. Awesome schools (Fairview South is the best) and a heavy Jewish population. Wonderfully integrated with all backgounds and nationalities, which is one of the reasons I've lived here for 10 years and am raising my kids here. Niles West is a great school and has the #1 Fine Arts H.S. Program in the country.
Not many "middle class" families in Wilmette and Glenbrook South district.