Might have to do San Juan. Only 3 real options from Chicago.

It's looking like Nassau from Ft. Lauderdale is the closest inexpensive(ish) option near MCO. I don't mind the drive to FLL, I guess. Gonna be a same-day, in-and-out type of thing, though.

Edit: Looks like JAX-FLL is even better. Sweet!

How long has it taken people for SPG points to transfer to Virgin? And was that done thru SPG or AMEX? Am I screwed by transferring this morning at 8:30am thru the SPG website?

Quite possibly

My partner submitted the request on Wednesday, 11am and the points posted about 30 hours later on Thursday by 5pm. EDT

It's done through SPG. I submitted mine yesterday at around 3pm and it came in today around 11:30am, so less than 24 hours. No guarantees, but you will likely be just fine.

Wouldn't JFK be cheaper?

Does it make sense to make a Wiki with easy ITA searches to try and find the cheapest flights available? You can use advanced routing codes with B6 for both the outbound and return to specify Jetblue flights and set the calendar of lowest fares to 0-day flights to try and create mileage runs with the quickest turnarounds possible. For JFK, I plugged in AUS, BOS, BUF, BTV, CHS, CLT, ORD, DAB, FLL, RSW, JAX, MSY, MCO, PWM, RDU, ROC, SAV, SYR, IAD, DCA, PBI, HYA, MVY, ACK, PSP, SRQ as my list of possible flights, leaving out the other destinations because they were sure (either via taxes or typical fares) to be more expensive. Just make sure you uncheck "Allow airport changes" before you search, so it looks something like:

http://i.imgur.com/XAb8ohV.png

I've found that most of the cheap Jetblue flights out of NYC during the promotion's timeframe end up being immediate turnarounds to BOS and ACK (Nantucket), where you can be back at JFK within ~2.5 hours of your departure. These flights, especially the ACK flights, are almost surely the same aircraft handling the inbound/outbound. It wouldn't take much time to make one of these for most of the cities B6 serves.

Thank you for the feedback, I submitted early Sat morning and points were transferred by early Sun morning. Submitting screen shot now.
Thanks again

The desktop screenshot worked and now I am registered (50,001 points)

Yeah I don't know if I feel like going to NYC in August though.

My MR is to LGB from LAS with a 2.5 hour layover.

Any clubs or decent food at the airport? Or anything worth Ubering to, food or tourist?

Has anyone received enrollment confirm over the past 24 hours? Looks like they may have taken the weekend off.

Anyone knows if "by 7/4/2016" means by the end of that day, or before it starts?

Possibly. There's a couple good restaurants at the airport. Going back through security will take you 3 min with pre. If you look up in yelp, there's a couple family owned restaurants around the area. MVP burgers, 10 min drive. There's more, easy search.