There is no chance that Israel will be added to the VWP in the near future. While Trump had indicated they were willing to overlook some of the obstacles, doing so would require granting the US access to the biometric database in Israel. That set off a firestorm in Israel, and it doesn't look like either side is willing to concede.
I also think ORD makes the most sense. There is logic of IAH, especially as a connection point to the growing travel from Latin America, but ORD seems like more of a low-hanging fruit, especially after LY left the market reportedly NOT due to lack of demand, and LY has indicated they want to return, so marketing it first would beat LY to the punch.