This kind of question is impossible to answer without more details. What are the dates of your flights? What is the equipment? How do the coach and business loads look now? etc. etc. etc.

If your trip is this coming weekend and both flights are J7, then I'd say you have a decent chance.

End of April, last I checked on EF there were 7/8 open J seats on the outbound but its more than a month away so can' t. really count on that. Just wondering if that is a popular route that people pay J or if upgrades are easily attainable.

Love it when a domestic trip has 9 open in F (based on seat map) but no upgrading going in 25 hours prior to departure. You can book this flight in F class - no problem (they don't even have a flag saying "# seats left").

T-4 days and it's still wide open F6 A0 J7 R7 D7 I7 W3 P3 Y7 B7 H7 K7 M7 L7 G7 V7 S7 N7 Q7 O7 E7
Just waiting for that C inventory to open up!

GCM isn't notoriously harder to clear than other Caribbean routes, or anything like that, the problem is that a majority of the MIA-GCM schedule has gone 319, which is hard to clear on any route with only 8 seats up front. If you can find a 738 flight you will definitely help your chances, but personally on a flight as short as MIA-GCM I'd just pick the best schedule and go with it.

Single data point, but I flew a MIA-GCM r/t last year in late May and didn't clear either way (319 both ways).

Neither ORD or JFK will be materially harder or easier to clear than the other. If by midweek you mean a Tues or Wed then you shouldn't have any trouble clearing on either, Thurs can be a bit tougher but still not too bad (same goes for pretty much every longhaul flight in AA's system).

JFK-LHR has never been a difficult upgrade, there is so much capacity between AA and BA that paid demand tends to be spread out.

Same for ORD-LHR, although all else being equal I would probably try to avoid the first evening ORD-LHR flight (~5pm), IME that one tends to fill up first.

Thanks for the DP, I'm not changing my flight for a better chance though. My flight only has 8 but I was just curious since I wasn't sure how popular a route this might be, let's see what happens, im sure it will be harder since there are 2 of us on the PNR, both about equal gold status give or take a few dollars

I'm not sure what your rolling EQD is, but mine has been around $20K the past couple years.

I have never missed an SWU on DFW-LHR or LHR-DFW. I've flown on every day of the week, and various times (though never on the first DFW-LHR (20/50)). I find that the first LHR-DFW flight (around 9am) is usually pretty easy to clear. The last flight of the day has been tougher lately... as I've been upgraded on that one either on the plane or within 4 hours of departure.

FWIW:

Type of Upgrade shown on my PNR has changed from Systemwide Upgrade to Milage Award. Apparently the phone rep has mistakenly removed my SWU when updating the payment terms for LHR departure tax. Just called to change it back. Not sure if this is a one time thing or system bug.

Chances for the following mileage/copay upgrade? Put in request today for mileage/copay upgrade wait list as there are 2 seats showing open and 1 blocked in biz on Expert Flyer (just open on seat map, not available for upgrade award yet) for the A330 with 20 biz seats, premium economy and economy cabin (with some Main Cabin Extra seating in economy). More details below.

Status Details:
Exec Plat just shy of $20k rolling 12-month EQDs. Currently approaching 50,000 EQM already for this year.

Flight Details:
PHL-MUC, 3/7/19 (evening flight). AA metal, Plane type 332 (Airbus 330). Main Cabin Extra (not PE, but economy), booking code N.

As stated above, I requested mileage upgrade with $350 copay and ExP desk said there were three seats, but the blocked is probably a crew rest hold that could be opened given this is only an 8-hour flight. Said she can't tell me more than that I'm the only one that's requested mileage or SW upgrade. Not using SWUs as I only have two left and am saving those for return flight upgrade wait list from Rome in April for wife and I.

Just curious if I should have just seen if AA upgraded me for "free" either before or at desk due to status and open seats, or is using miles and cash the best option for getting bumped. I've heard that sometimes they'll just give the last couple of business class seats to CK or EXP during pre-boarding, but then again sometimes they'll opt to give those to miles/copay because at least they're getting something $$ for that vs. just handing them to EXPs/CKs for nothing.

Thanks in advance.

The odds of you getting op-up'd to biz from economy are almost non-existent. It happens from time to time, sure, but very, very rarely.

I would keep your Miles+Copay request to upgrade.

What I figured, thanks. I have also seen at mobile check in offers from AA to upgrade for $550 straight up, which took advantage of a couple of times last year.

When do the mileage/copay requests usually get processed? Within a certain time prior to the flight, at or after check-in (T-24 hours), or at the gate? Can't recall a time I've used miles to upgrade for overseas flights via a wait list as I've always had 500-mile tickets for domestic (or complimentary domestic), or done the $550 cash offer at check in.