I've used two pediatric dentists here. One was Kids Plus pediatric dentistry in Wicker Park. http://www.kidspluspediatricdentistry.com/
They are great at making the children comfortable, but they are very interventive. I would use them again for exams for small children, but you have to be willing to stand up to the dentist if she recommends something your not comfortable with. (Like pulling all their teeth out at age six because they're taking too long to fall out.!) But really, if you have a child who is afraid or uncooperative, this place knows all the tricks for keeping kids happy. Who knew fillings could be fun?
Now we go to ABC Pediatric Dentistry in University Village. http://www.abckiddentist.com/
Dr. Barnes is very respectful and conservative about treatment. She is huge on prevention. The kids don't like her as much because Kids Plus was more fun, but she is highly competent. I've come to like her a lot, although it irritates me that she likes for the parents to stay with the child in the exam room. For some kids, that might be a good thing. For others, not so much.