My advice (from someone who does this quite often): 'game' the system while you still can.
Just leave plenty of lag time in between the trips (at ORD) and you'll be fine. Plus, if things go on time and you get to ORD with say 5/6 hours between flights, take the train into town and enjoy Chicago for a few hours!
You'll get the extra miles, enjoy Chicago (hopefully), be a 'smart' consumer and best yet - SAVE money!
Keep those buffers in place and enjoy your trip (although it isn't crazy, at all - some folks here will tell you it is) to TLV!
Read about the EWR-SEA two years ago for crazy places to go en route to Seattle...now that was a fun experience
-jeremy