Join Date: Jun 2004
Location: Santa Monica, CA
Programs: AA EXP 1MM, UA Silver, HHDmd, MBvLTPLT, PCAmb/Dmd, HYT Dis
Posts: 1,579
My best surprise was 2 years ago. Had booked an 2 business awards (1 with UA miles, 1 with CO miles) open jaw into Bangkok on Thai and out of Phuket on Thai/UA because we were going to make a few stops in between. But then we decided to just drive places from Phuket, and only needed 1 intra-Thailand flight. If purchased separately was looking at a few hundred in additional cost for the BKK-HKT flight. Was able to call back and add the leg for free - and in business class.
I was also able to do something similar a few years ago adding an extra flight between Brazil and Argentina on what was originally an open jaw into Sau Paulo and out of Buenos Aires (adding the leg for free).
Other open jaws (business awards) I have done in the past decade -- most are 2 week trips:
Into Rio and out of Santiago crossing Brazil, Argentina, and Chile in between
Into Warsaw out of Prague with Poland, Budapest, Austria in between
Into Melbourne and out of Auckland seeing Sydney, Brisbane, Cairns, and the south island of New Zealand
Into Rome and out of Palermo driving down the boot and around Sicily
Into Tel Aviv and out of Cairo
Into Paris out of Amsterdam with a fair amount of time in France then up through Brussels
I also travel to St. John's every other year and have been able to do stopovers in Atlanta or DC to see family or Puerto Rico to your around there.
Into St. Petersburg and out of Copenhagen with Moscow and Sweden in between is next this summer.