Barrington is a beautiful suburb with large yards, forest preserves and the calmness of country life. Kids can run around the neighborhood. Chicago is vibrant with lots to do but we would be living in an apartment or maybe a very small house with no yard. He wouldn't be able to run around the neighborhood without me.
It's a myth that kids run around the burbs on their own more than in the city these days. Unless it's a very very small town, and I don't think anything that is a suburb of Chicago is a small town. I did live in the burbs of Chicago through 2nd grade, and in the 70's we walked to school by ourselves (in K) and played outside without parents. I know of a family that lives just outside Chicago and they still walk their 3rd grader everywhere. I'm not sure kids running around town happens ANYWHERE in the U.S. anymore. (Certainly not where I live & it's supposed to be suburban.) In the suburbs things are farther away and there is usually not as good public transport turning parents into taxi drivers until the kids old enough to drive. There are pro's & con's to the suburbs and the city. I'm just saying don't put on rose colored glasses thinking the burbs are the best place for growing up.
As to where is the best for the kid to go to school. Hard to say until you are in the situation and as polarbear also mentioned. If you are in the city now you can try that and see if it works. I assume you won't know for a while if he even gets into the gifted school. It's fine to decide that isn't working for your family and move in a few years. Don't move just for the school district.
Good Luck.
