Book a mileage ticket with a stop over one of the ways? Can You?
For example in my case; This week I want to fly out of a New York area airport, fly to Montreal (make a few hour stop or even maybe overnight) and then continue to Los Angeles. But when I return, I want to fly directly to the New York area.
I can fly with American, United, Continental, or Delta (or any airline that you can transfer Amex Rerwards out of)
Thanks
P.S. I think using united I can fly with air canada as well
This raises the question of the inherent unfairness of charging a fee for making bookings via telephone that, because of AA's own decisions regarding aa.com, cannot be booked any other way. I raised this point with a telephone agent a while back, in the course of booking an award with both a stop-over and an open-jaw segment. They wouldn't waive the fee, but they gave me a roughly comparable number of miles. You might want to mention that too, on the chance that you'll get something and to keep reminding them that they ought to fix that unfair policy.
Continental allows a stopover but it costs more and has to be on the routing anyway (in practice this means at a CO/NW/DL/AS hub, with a few exceptions). So that wouldn't work here.
I don't know about Delta.
You can on an overseas trip do in some situations an overnight stopover of less than 24 hours and then do another stopover overseas.
most obviously it happens like this
IAD-sfo arriving 10 p.m. (stay in a hotel overnight)
leave sfo at noon to hkg (you can stop there)
then hkg-sgn
but if you stop in hkg going for more than 24 hours, you can't stop coming back.
I think a connection in the originating city is fine on an AA award, as long as it's a true connection (a few hours) and not a stopover. But, since as you point out, this must be booked by phone anyway, it's easy enough to ask then.
For the OP - this is the key issue. You should be fine for your itinerary provided you find something that is allowable routing. I'm guessing, but you might try a Star Alliance award with Air Canada being NYC - YUL - LAX part of your itinerary, and UA being the LAX - NYC part of your itinerary.
Actually, it's extremely simple. One stopover is allowed on any award between two geographic regions. No stopover is allowed on any award completely within one geographic region.
You can on an overseas trip do in some situations an overnight stopover of less than 24 hours and then do another stopover overseas.
Anything less than 24 hours is not a stopover.
Once I decided to use my miles for a round-trip from Caracas to the USA and back, and this was my itinerary:
Day One: Caracas-Miami-New York
Two Weeks later: New York-Miami
Six Months later: Miami-Caracas
Decide for yourself. I did it in Venezuela on the phone (Not online, and not on the phone in the USA, 'cause they aren't too nice about it)
This raises the question of the inherent unfairness of charging a fee for making bookings via telephone that, because of AA's own decisions regarding aa.com, cannot be booked any other way...
Somewhat off topic... I also find with United that, with a live reservationist, more Saver Award itineraries open up when the objective is a transcon RT. And often connections are available, when nothing shows on the booking web page. Frustrating, but usually in the event, I'm more relieved to get the trip than p.o.'ed. This has happened many times.
Still, and to the OP's question: No stopovers on UA domestic. For DL, there's this thread (I don't know how to do the link thing):
New rules, mileage levels for SkyMiles award tickets (Routes, Conx, Stops, Open-Jaw)
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