Good job planning ahead! Don't forget to have your brother start watching hotel rates early too!

Updated to add what I just booked for a 10-day vacation in Mexico in October.

OKC-MIA-MEX. 8k

MEX-DFW-BZN in F. 20k


Booking well ahead of time, flying on Tuesdays and Wednesdays, and checking rates often, I have also snagged excellent deals with miles. I regularly get two to three cents per mile valuation when I do this. Some examples are

BIL-DFW-GTR. 6k

GTR-DFW-GJT. 6K

GJT-PHX-SFO 6k

SFO-PHX-BIL 6K

MSY-DFW-SMF in first class on a Friday! 21k

There are probably are not a lot of people on this board that fly to Billings, Grand junction, Columbus/Starkville/West Point, and other smaller airports. I do, and I regularly get excellent mileage redemptions. I almost always get upgrades on these types of flights as well, and it is very much a sweet spot with AA. I am self-employed, fly approximately once a week, and put all of my business expenses on the American airlines credit card. lately, about 2/3 of my flights have been purchased with miles, and I have over 200,000 mi in the bank. Flying American, using their credit card, and booking early has allowed my personal business to be quite a bit more profitable. In the case of Billings, which I go to at least once a quarter, cash fairs are quite high. I have sometimes gotten up to $0.04 per mile valuation out of award flights to and from Billings. Strangely, but perhaps because it is a tourist destination, Bozeman is opposite. Bozeman often has cheaper cash fares and higher mileage redemptions. I work all over the state, so Billings works just fine for me.

In my searches, I noticed significant differences in price based on the day of the week. For example, the Tuesday flight might be six or seven thousand miles, and a flight on Friday, Sunday, and Monday might be 26,000 miles.

The flights to Sacramento are on the upcoming Friday April 4th. I have a suspicion that those upgrade lists are going to be miles long with several high value customer sitting MCE. I'll be sitting in first class for 21,000 miles. I often fly into Lafayette or Alexandria when I'm working in Louisiana, but I decided to take a few days off in NO there during this trip.