I'm booked with my (adult) son on the same trip in mid-May, but it's a little more expensive: $764. Still, the fare from nearby CLE is a whopping $1,326. Thus my savings by starting in ORD are way more than $300. Fortunately, ORD is only 367.9 miles away from the front door of my palatial digs, so we're driving there and back and splitting the gas money.

RNE, realizing that NYC is 800 miles from ORD, but still, driving is a possibility.