Here is a good road trip airfare between Chicago and Los Angeles or San Francisco at $112 one way, $223 round trip with American Airlines. This fare has been around for more than a week with flights on Tuesday, Wednesday and Saturday lowest fares from late August to December 2015.
Welcome to the California Coast Road Trip
One of the features for this fare is the ability to fly from Chicago to San Francisco or Los Angeles, rent a car one way to drive north or south along the California coast and depart from the other airport. You can fly Chicago to Los Angeles, and drop the car off in San Francisco for your flight home with one open-jaw airline ticket for $222.20 round trip.
American Airlines Chicago ORD Los Angeles LAX/San Francisco SFO – Chicago ORD
$222.20 Tuesday September 15 – Tuesday September 22
San Jose SJC and Orange County SNA routes are about $15 to $20 more each way.