Rather than booking a standard RT ticket online for the 500 mile bonus, could I book two RT tickets, using the outbound on one ticket and return using the outbound on the second ticket. I would then get a $ refund on the two unused portions of my ticket, but get the 500 mile bonus twice. What do you think?

This is kind of a grey area. If you are doing this on full-fare tickets, it would probably work. Bear in mind that the two one-way full-fare tickets (the parts you'd be left with in the end) are in all likelihood going to cost more than the single round-trip ticket.

If you are using discount tickets, cancelling the return leg of it will result in a recalculation of the fare, possibly requiring upgrading the fare to a one-way full-fare. Same thing for ticket number two.

In all likelihood the extra cost of the ticket vs that of the single round trip ticket is not going to be worth that extra 500 miles (nor the extra time you'll need to spend changing tix, cancelling segments, etc.)

One thing you might want to consider is that if you are flying from A to C, consider breaking the journey at intermediate point B. Book ticket #1 A-B, B-A and ticket #2 as B-C, C-B. This is called end-on-end ticketing and is perfectly within rules and regs. This would get you the second online booking bonus, however again pay attention to what this does with the airfares. If B is a hub airport, usually this will give you a higher total airfare than if you were to book the through fare A-B-C, C-B-A as one itinerary. The other thing is that if you are checking baggage, it's more of a hassle since you'll have to reclaim it at B and check-in there again.

Hope this is helpful. The real experts will now chime in.

FewMiles..

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I think if you're booking a oneway fare, that you will get (2) 500 mile bonuses for a round trip, one each way.

Since, as fewmiles says, this only works with full fare tickets, you might as well follow nologic's suggestion and buy one-way tickets in the first place. AA, which offers a 1,000-mile bonus for a round trip, gives you 500 of the miles for each direction you actually fly, so buying round trip tickets wouldn't increase your bonus over buying one-way tickets.

Delta seems NOT to give the 1000 mile web booking bonus on r/t tickets if any part of the itinerary or flights are changed, including non-use of one leg of the trip.

When 1000 miles is offered, it is posted as 500 each way. You won't gain anything only using one way of a RT ticket because usually one way fares are more expensive. I have booked a cheapy RT and only used one direction (ORD-LGA) and it was a lot cheaper than a 1 way would have been. I got 500 miles, not 1000 because I didn't fly the return.

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DtG