Hi S.,
Check out www.kidwinks.com - it will help with your hair cut question as well as with living in Chicago with kids in general. Go to the Services section to find hair cut places; check out the Events Calendar for a calendar full of things to do with the kids, including free days at museums & zoos, festivals, concerts, story times, open play days, etc. Go to the Restaurants section to find kid-friendly dining places, and use the Kids Eat Free Calendar there to find out where kids eat free or cheaply any day of the week. The Ongoing Activities section is great to peruse when you're stumped for something to do anytime - bowling, mini golf, indoor play, etc. Become a member, which is free, and you can sort any of these search results by distance from your house.
J.