Chicago house values have been quite stable in certain neighborhoods. The South Loop condo that I sold 5 years ago has barely appreciated in value, while the condo I sold 4 years ago in the Boston area has gone up 70% since.
People put a lot of value in walkability and nearby amenities.
As far as large American cities go, Chicago is extremely child friendly and child-focused. The attendance area for the neighborhood schools are small. Chicago Public Schools has an excellent mapping tool - don't trust the real estate listings. They lie.
City employees in Chicago are required to live inside the city. The northwest side has a heavy concentration. On one block every third house will be a policeman or fireman. On another block it will be streets and san workers. Then teachers. Etc. It does affect the character of the block :)