How many months in advance do you - on average - book flights?

I usually check that but so far I haven't found that to be the case. The only extra is that if I purchase insurance, I'm buying it for 2 trips instead of just one. I fly JetBlue, btw.
Back when I was mostly flying JetBlue that was also my experience. But Delta it's iffy. Most of the time it's the same, but once in a while it's not, so I've learned to compare pricing.

The DTW based Delta Crew, asked for my PDB order as soon as I took my jacket off, asked if I wanted another as soon as we got above 10k, meal service was good and they were around but not overbearing for the rest of the flight. All I had to do was make eye contact and they were asking what I would like.

This has been my general experience with JFK based Delta crews. Never missed a PDB and always great service throughout the flight. I have a soft spot for them after the way they took care of me when I flew down south immediately after my mom died last year. I was understandably a mess and they treated me with a lot of care and compassion. I emailed Delta to commend them.
 
Word of caution with Frontier, one of the companies I work with tried to save some money and sent a co worker this weekend via Frontier. Price was about $200 less, but half of that was immediately eaten up by the cost for a carryon. He was scheduled to fly out last night at 1130, at 11pm they cancelled his flight with no warning and no help. No other flights home that he could make with the late notice. So now the company has to pay for a hotel, transportation, food and buy another ticket on another airline as the rebooking offered was Tuesday night. If it had been a personal trip, he'd have been on the hook for all of it. Total, the company's attempt to save $100 is going to end up costing them about $600. At least if this had happened on a non-ULCC, he would have had a good chance of getting his hotel paid for and would have flown out one way or another first thing this morning.
Yes, agreed. The rate I mentioned above does include a personal item and a carry-on. The R/T on SW is $800! I'll see if it comes down in the next couple of weeks though. How much is my peace of mind worth?!?!?
 
Perfect example of what we were talking about earlier...I just checked our May flight down (one way), originally booked for 11k Skymiles pp including the Take 15 Amex discount. I saw it had gone down to 8900 so I canceled and rebooked at the lower cost. Got my miles back immediately and taxes back on the card.
 














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