I want to book a multi-city trip originating from the east coast and going to the west coast and then back to the east coast with a week long stop in a USA destination inbetween.

Essentially I want to go from YQM (Moncton) to ORD (Chicago) to YVR (Vancouver) to YQM. Because Moncton is so remote it always take at least one stopver in Toronto or Montreal to get anywhere.

Is this possible to do with only 25,000 miles on a class rewards flight? I tried very hard on the website making sure to use unpopular flights dates (wednesdays) almost a year out and the best I could get was around 67,000 miles on a ClassicPlus.

I am pretty sure I heard others say that this is possible. Is the reason I'm having problems because I have a total of 3 stopovers and therefore 6 segments to the total trip? Is that too many segments for a multi-city trip? Is it because Air Canada doesn't operate its own flights to some of these cities?

I tried the same thing but substituted both YYZ (Toronto) and YYC (Calgary) for ORD and with choosing unpopular dates was able to get a flight for 25,000. However, in both of these case there were only 5 segments to the trip instead of 6.

Thoughts and helpful suggestions please ^