Quoted from LTG:For that cheap I'm surprised you aren't required to be peddling to power the propellers.
LTG : )
Round-trip flights from O'Hare are frequently cheap in the fall, and silly cheap in the winter, especially to Los Angeles, San Francisco, and Oakland, which are often $150 or less. My latest is ORD -> SFO round-trip, $81.80, inclusive of all taxes and fees. I have done it for as low as $58, and have seen it as low as $38, all inclusive.
You just need to plan ahead, be on the right mailing lists, have flexible travel dates, play their game to your advantage, and pack very, very lightly. A lot of these fares are one-day sales, and usually require flying on a Tuesday or Wednesday. Even if you only fly one segment on a Tuesday or Wednesday, you'll still usually save a ton of cash over nearby days.
Exclusions to the cheap fall-winter travel:
Thanksgiving week and Christmas-New Year's, which are high demand and expensive.
$116 from (assuming Boston) is still damn' good, though!
-Mark