In that case my recommendation is to look along the Brown Line. The schools are good, easy commute to the Mart (L stop is connected to the building). For ORD, all the major east/west streets have buses that will take you to the Blue Line. If you're anywhere close to rush hour, the Blue Line will be faster than the traffic on the Kennedy.
I was thinking the same thing. And the OP may want to consider expanding his neighborhoods to include the part of Lakeview near the Brown Line. The area around the Southport/Roscoe stop is far enough away from the crowds at Wrigley, it's a very safe and family-friendly neighborhood, very close to all the restaurants on Southport, and there are a lot of single-family homes in that area...and those that are for rent should fall under the $5,000 limit.
A couple stops further north of the OP's office, but might even take less time on the train since it wouldn't require a connection.