We love Dr Fred Ettner - he's a family doc in Evanston (south Evanston) but that's not far at all from Andersonville. It's only a 20 min drive for me, and I'm farther south, in Lakeview. He's very pro-BFing, ok with skipped or delayed vaxing (doesn't recommend vaxing babies younger than 6 months in most cases), fine with all AP parenting, not prone to suggest lots of interventions, etc, and very competent. I also love that when I call after hours or on a weekend, he answers directly (has office phone routed to his cell).
For preschool, Rogers Park Montessori (actually in Andersonville) is supposed to be great, and I loved it when I visited recently, but good luck getting in... It's a lottery system, and is very popular, and their application period was back in March I think. We were told not even to apply for their toddler program, since all the spots were taken up with siblings. I think there are more spaces for the 3-6 year old preschool classes, but I'm sure they're all filled now. We're going to send DD to Park View Montessori (at Irving Park and Lake Shore Dr) in September. Since we haven't started yet, I can't tell you much about it. I didn't like it as much as Rogers Park, but it had a lot more available spots (and will take people as they apply - no special application/lottery period).