Upgrade SFO-JFK/EWR

[SoftDraw]

Sorry if this is the wrong section to post this question.

I have an upcoming trip next week to America (booked on CX with Alaskan miles, flying into SFO and out of JFK). Myself and Mrs SoftDraw need to fly from SFO to New York on the 2nd of November or on a redeye on the 1st of November. The cheapest business tickets i can find are all $1500+ which is too much. Planning on booking an economy ticket now and was wondering which is the best airline to book with that will give us the most chance of upgrading with either cash or miles (I have a large amount of SPG points so could transfer to the relevant program). I have read of United offering cash upgrades within 24hrs of departure. Does anyone have any recommendations to increase my chances or any previous experience upgrading on a Transcon in America?

Thanks in advance!

 

[Danger]

Well there's a lot to consider in that.

First, I have no knowledge of SPG except to say I don't think it's a partner with AA. Regardless, even if it is, AA doesn't allow you to upgrade with points unless you have status and even then it's a bit more complicated. Also, the chances are upgrades on their three class transcons will be taken by status passengers.

Second, have you considered flying indirect? Both AA and UA have flights via ORD and/or IAD for less than USD600 in "First". (UA is into LGA.) AA also has one via DFW at 12.40am and into EWR at 11.55am for USD569.

Third, Alaska has a direct SFO-JFK in "First" for USD899, departing 11.25pm and arriving 7.48am.