Buying two tickets with points, three without on Delta

I think the only way you can do these together as one reservation to "pay with points" (assuming Delta still offers that). Then you are using your points as cash (100 points = $1 off IIRC).
 
I've never booked mine together. I just book the tickets with points and then book the cash ticket on a separate reservation. Later I call and have them linked. I supposed if you call initially someone could help you book them all on the same reservation.
 
Be careful with Delta, they change schedules often. Keep an eye on your reservation, I almost always had time changes if I booked more than a couple months out with connections. I actually intentionally used that to my advantage. One time I was booking frequent flyer tickets for myself and a friend. The flights they had for the lowest points was late morning departure, PIT-JFK-MCO. Really didn't want to connect at JFK, seems like a waste to fly east to go south. I gambled that there would be a schedule change and took it. Sure enough, there was a time change, our flight arrived at JFK at the same time as the MCO flight left. I called and got the early morning flight through Atlanta that I really wanted for no extra points.
 






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