Vogue – I’m sorry to hear that, and I’m not sure when you went there but in every school some kids have bad experiences. I went to Hanna Sacks and had a great experience, the ruach was amazing, and preparing for erev shira after hours was really fun and really bonded us in a way that we were not able to during school hrs…my only hard times during those years were from things at home, not school.
Morah Rach – If family is priority I highly recommend Chicago, as it’s only a 1.5 hr flight, and even though it takes a while (I’ve heard about 18 hours) it is drivable (I had friends that drove to NY every succos and pesach with 5 kids, sometimes stopping in cleveland for a night). Most of the weather, New York gets a few days after Chicago, so you shouldn’t find that particularly worse. Besides that, you actually have PARKING wherever you go, you usually go from and back into a garage for that half a yr. (BTW we had an automatic starter on our car so we could start it automatically from inside the house in the winter months – no de-icing! By the time we came out the car was warmed up, with heat and we could drive right out!)
It’s a really well organized community (the achdus guide which is a community white pages & yellow pages, the vaad tzedakos that approves a green card for legit tzedakah collectors only, likutei pshatim which is a weekly parsha sheet with community classifieds which keep you up to date on events etc in the community), everything is clean and nicely kept up etc, and you have more restaurant options than a lot of “out of town” cities (oh and did I mention they have the best meats ever at Romanian? and a completely kosher bakery and deli with ready food at Jewel-Osco with a gigantic parking lot that always has spots)!
If you are undecided, next time your family has a vacation, you can rent there and check it out first hand. But if you plan to leave the tri-state area (and are not considering moving to E”Y)- I highly recommend Chicago – wholeheartedly.
(Not saying tri-state area is superior as I don’t think it is, but I know New Yorkers have a hard time leaving!)