Going to go from Platinum to Gold soon further reducing upgrade availability. But the good news is I aam retired and can choose when to fly. Are there better times/days to book flights improving my chnaces of snagging that elusive upgrade?

Saturday IMO....

Many business travelers pick Sunday evening or Monday morning flights to leave town, and return on Thursday evening or Friday. Flying on Saturday or mid-week gets you out of competition with the folks whose schedules align with a M-F work week. Sure there's plenty of business folks whose schedules don't align with that, but I think that's a help.

Holidays can be great for easy upgrades, but you have to be willing to travel on the actual holiday, not before it when everyone else does so that they are at their destination for the holiday.

Thanks, like the actual holiday travel

Normally I woukd agree, but FCM is a game changer IMO....

Example.. Got ug at the window for a Sun ATL - ABQ. I waited until. T-48 for the return Sat flight.

I also live in MCO, which Sat. Is a huge travel day here...

Saturdays are usually great for upgrades. Most times all medallions will clear and even have a few NRSA's clear. For me, Sundays have also been pretty good and then followed by Tuesday.

I also try to stay off the beaten path. Avoid ATL as much as a possible. I try and connect through CVG and JFK as much as possible. They have been excellent for upgrades. I only missed one upgrade this year out of CVG and I have never missed an upgrade out of JFK.

Routes matter, too, and not just days or connecting airports. Even on "off" days JFK isn't exactly an easy UG for LAX/SFO, and SEA/PDX can have double-digit lists of elites who don't get to sit in front. I've been on Saturday LAX-JFK red-eyes with 30+ elites in Y, and Wednesday JFK-PDX flights that, especially with FCM, can only clear one or two UG.

Of course, YMMV. I've never tried JFK-LAX/SFO. I can imagine with only 16 F seats on the 757 that it is a tougher upgrade. As I've said, I've never missed an upgrade out of JFK. Here are the city pairs for just this year:

JFK-PHX
JFK-SAN
JFK-LAS
JFK-DCA
JFK-MCO

I wouldn't expect JFK to be an easy upgrade because of the BE international connections as well as those elites who buy M+ for the upgrade.

Good point. I will say the only upgrade that surprised me ex. JFK is SAN. It was a pleasant surprise to get it. The others, PHX,LAS,DCA,MCO, are leisure destinations and most folks going to DCA from NYC are probably going to be utilizing LGA or EWR.

I wouldn't call DCA leisure, but I agree with you that most business travelers to/from DCA would use LGA or maybe EWR--or even Amtrak.

Flew ORD-MSP last Thursday 3pm and back Sunday 9am.

ORD-MSP Thursday: 54 on the upgrade list for the A319 with 1 F seat open; was first in line at the counter to ask to be moved from middle to aisle or window - - she said there was one potential no-show - - after that the message appeared that no more seat changes were possible; got the aisle in row 17 (a Diamond sat in the middle).

MSP-ORD Sunday: A woman with 5-year-old daughter walks up to the gate; then walks behind the counter and types at a monitor; later I see them together in 1C&D on the CRJ900; a pilot is sitting in front of me in 3A; as the door is closing an FA brings a uniformed serviceman forward and gives him 1A; two of the twelve F seats go out empty.

This sounds like a nonrev sat in FC with a child who is too young to fly nonrev in a premium cabin. This should be reported.

What's the minimum age requirement on nonrevs in a premium cabin?

I'll tell you when NOT to go. Friday afternoons. I'm always flying Friday afternoons and I'm usually #32 of 50+ as a GM. Usually I'm going DTW-ATL-PBI. If I ever get upgraded then I'm expecting at LEAST 3 shenanigans threads to show up.