Which flight would you book between nyc and msy
 

leaving on the 15th of oct returning on the 20th
silver medallion
delta reserve
looking for my best chance for an upgrade
when i try to at least book H class on line, my returns are all Ts.
would you wait a bit? book now?
advice?

I just found all H fares with a stop in ATL both directions.

2019 EWR-ATL 737-800
1729 ATL-MSY 757

1704 MSY-ATL 757
2014 ATL-EWR 737-800

All H fares $420. That was the cheapest and looked like the biggest planes. I don't know about the routes and the timing, but based on planes and pricing that is what I would book.

I fly to NYC every month and take the Delta non-stop flights between MSY to LGA round trip. DL began using NWA metal for these flights a few months ago which means that you will be on a Airbus instead of a commuter.

Oct 15: DL4124 LGA/MSY non-stop departs LGA @ 9:55 am
Oct 20: DL4134 MSY/LGA non-stop departs MSY @ 7:35 am

I usually book the cheapest fares available when I book and almost always get upgraded. In fact a few weeks ago I sat across the aisle from Nicholas Cage on the morning flight out of MSY!

I would also suggest the DL direct flights from LGA. I recently took a weekend trip - Friday night to Sunday afternoon...
The F cabin on Friday was... empty! There were three revenue passengers (me plus companion and another guy) and one non-rev. Talk about an easy upgrade.

The morning flight was also wide open (I booked it to get a cheaper fare and then SDC'd for the afternoon) - probably 3 people in F based on seat map. The afternoon departure was full-ish, maybe 11 or so, but still not at capacity...

There was even a random meal service on the evening flight to MSY! Left overs from the inbound MSP :D Nada on the return... ridiculous.

Hope this helps!