A.
We have lived in condos in the West Loop and University Village, and just bought a house in Bridgeport. If you are going to be in a condo, I loved University Village. Lots of green space, plenty of diversity, and I loved having the UIC soccer and baseball fields right there. They were often open to the public and made a great place for a toddler to run around. There were TONS of kids. I did not think the West Loop was very child-friendly at all, though it was extremely fun as a childless couple. We are very happy with Bridgeport - you can get a single family home for the price of a condo elsewhere in the city. (You can still get new construction with a small yard for under 500k here. Older homes are in the 300-400k range.) It is safe, 2-3 el stops from downtown on either the orange or red line, and home to the Sox. They are about to open an amazing park where the old quarry was located, and there are kids everywhere.