Are you thinking about getting out to ride with your kids and not sure what might work for you? There are plenty of resources out there - local and elsewhere - on biking with kids of various ages. Spend a little time browsing and you're likely to find info that suits your needs.
Scan down this page for an extensive list of women's bike resources.
Here's an impressive blog by a family doing lost distance travel by bike.
If you want to connect face to face, trying a Kidical Mass ride in another Chicago neighborhood is a good way to start.