I would like to go to Hawaii this summer with my wife for our anniversary. We have quite a few points in various FF programs. I don't have a problem booking it on my own, but I feel like when I've done it in the past, I have a hard time getting the best value for my points. For example, I spent 50,000 on a roundtrip coach ticket from MKE to SFO. I was happy because the trip was free, but in my reading I understand that my points could have been better used elsewhere. It might have been better to pay the $250 per ticket price. Anyway... I'm wondering if you could suggest services that I could use to get the best value for my points and miles. I know about Lucky's service, Point Pros. Are their other services like this that folks on milepoint would/could recommend? I think this will be the best way for us to get the most out of our travel. I did try to search the forums here and on flyertalk, but I can't find anything. Maybe I'm not using the right keywords. EDIT: As requested below. We'd ideally like to travel mid-summer (most ideal would be over July 4)... but we are flexible and could travel anytime June - August. Our home airport is MKE, but ORD isn't bad for us either. We are okay with layovers and have family near San Francisco (SFO) or San Jose (SJC)... so if there were good deals from those airports, we could do a long layover if needed. My points. OnePass: 30,000 US Airways: 47,000 AA: 46,000 Club Carlson: 55,530 Starwood: 8,228 Wife's points: OnePass: 75,000 AA: 61,000 Plus we have $200 in American Airline travel vouchers... soon to add another $200 (from AMEX platinum).