Try your "Hardest" to stay away from having to drive on I-80/94/90/65.....it's always under construction and always backed up because of the toll booths.....They just showed it 12 miles of back up today, on a Sunday, and it's 100000% worse during the weekday/rush hour.
I can't suggest anything about schools as I'm single and live here close to Wrigley Field for partying purposes, which is nowhere near midway. However the cities west of Chicago, like Naperville, Batavia, {Yorkville & Oswego are really family friendly safe newer affordable communities}, Planefield, Joliet are all pretty safe areas in Chicagoland. They are "west" of midway and traffic coming from there to midway is not as bad as from Indiana or Michigan.
Midway airport is located of I-55.........be advised that I-90/94/80 (and some parts of I-57) all connect and are under construction usually where they are merge is from 4-5 lanes from each interstate to a total of 2 lanes.....traffic sucks......If you live west (the towns I named) you won't have to worry about that.
Good Luck.....oh and those cities have METRA train stops so if you, the wife, and the kids ever do want to come into the city of Chicago, just goto the Metra stop in your city, park your car, hop on the train and miss all the traffic.
www.metrarail.com