Any Airmiles travellers on here?

[monster]

I need a flight. I'm an Expedia booker usually. But I have a shit ton of credit card reward points (Chase). Usually, I just cash them in, but I thought maybe I should try and spend them, I'd get a better deal. So I clicked on their "spend it on travel" linkie .... and it seems no better than taking the cash and booking through Expedia. Am I doing something wrong? (well obviously, but what? ..be gentle)

I have an acquaintance (kids went through k-8 together) who blogs about these things and his exploits make me feel I should be able to get a better deal, but I'm clueless. I'd ask him, but he's currently busy researching trying to get as far away from home as possible with 40K airmiles and $400 ...and well, you know... just fucking socially awkward. (But you guys don't count )

This guy lives for airmiles, he's way out of my league for sure. He mostly opens cresit cards for their bonus miles, and managed to get enough to get a trip to Necker and hang out with Richard Branson

(https://frequentmiler.boardingarea.com/)

TIA