Chicago i know is a great city it is small and has a very warm and out of town atmosphere that is extremely unique, but it is not as small as the other places you mentioned, making it feel less of a hick town. If you want very small Chicago may not be what you are looking for, although most people pretty much know everyone, it is not as small as the other two. We have great schools here. Chicago is very lucky to have two main elementary schools which are great. They are both very warm and supportive in all areas. For high school,We have telshe yeshiva, which has a dorm and is a great school, and we also have a yeshiva called meohr hatorah also a great school but no dorm. They have shorter hours as well. Again Chicago is an extremely warm city very nice people and great atmosphere from what u said it def. sounds like it may be the place for u, but check it out more If u have any other questions feel free to post!
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