Moving to the City of Chicago - Chicago,IL

You might want to consider the close suburbs: Skokie, Niles, Park Ridge

With the housing crash those areas are now affordable. The Maine Township schools area good--especially Maine South (high school).

Some of the better neighborhoods are Edison Park, Portage Park, Norwood Park, Jefferson Park, Sauganash, Ravenswood

Edison, Portage, Norwood and Jefferson Park would all be very close to the Blue Line train, so that might be a good option for you if you are open to public transit. The METRA also goes through there too.

I lived in Rogers Park, Edgewater and Des Plaines during college, and worked in Skokie. I wouldn't want to raise a family in Rogers Park or Edgewater these days--lots of crime.

ETA: Be prepared to adjust your expectations. Compared to Elgin, Chicago will seem incredibly cramped, even in the nice areas. I was just driving through the areas I mentioned and it is just a totally different feeling than I have when I am driving in the western suburbs. So congested; houses so close together and so old; longer lines at the stores, etc. It is a huge adjustment.

I live west of O'Hare, but my nephew and family moved to Oak Park. The train goes downtown and they live in a wonderful family neighborhood. They have two little ones. I grew up in Rogers Park and loved it! wound up out here but would love to be back there if it were ever possible.

I would call Janice Weiner. She is a Realtor with Re/Max Suburban. She would be able to show you homes and answer questions for you. Her cell is ###-###-####.
Good luck to you!

Depends on what you can afford, generally things get cheaper the farther out from the Loop you go. Do you need to be near a train line? Do you want to be close to the lake? I have lived all over the north side although once we had kids we went further west. My sister and good friends live in west Lakeview (almost Roscoe Village), I have friends in Uptown and Rogers Park and Edgewater and Lincoln Square. Each area has its pros and cons, so it sort of depends on your budget and what's most important to you. Some schools are much stronger than others (Blaine and Bell come to mind), but there is also a lottery structure where people can go outside their boundaries. Generally the school system has gotten pretty intense -- my 6th grade niece is stressing about where she wants to go to high school because 6th grade tests help determine placement, it's insane. But you won't be completely locked in based on where you live, so keep that in mind.

This may be a good resource for you: http://www.npnparents.org/