I'm going to book a flight from Boston to Ft. Myers for a trip at the end of March. I need to do this soon - like tomorrow soon. Prices have already gone up a good bit since I started looking. I have Southwest points, but Southwest doesn't fly direct and will take 8-9 hours for a 3.5 hour flight. So I'm looking at alternatives.
I have plenty of URs, but currently don't hold a card that allows transferring points (I have CFx2, CFF, CFU, CIU and CIC). I've considered upgrading one of my Freedoms to a CSR, but not sure how quickly that happens, is it immediate? And if I do that, would it be better to book on the chase portal or transfer points to an airline?
Or should I just book with a Freedom and use points towards it on my statement? The flights look like they'll be $200-$250 round trip with bags, if that makes a difference in how I should approach this.
Any opinions on best way to do this would be appreciated. Thanks!