I've seen a lot of low fares originating in ORD the past several months, but dates didn't fit. I know because, based in DTW (near Detroit), I often consider driving to Chicago to catch a good trip.

I suggest browsing the MR forum at least twice a day. Also, subscribe to the Fare Deal Alert and "The Flight Deal" daily newsletters.

Consider taking a cheap positioning flight to catch an exceptional fare. It is often possible to connect ORD on the way back, so you can end your trip there. This was the case for the May/June DCA-ORD (or DFW) -PEK-ORD (or DFW) - DCA business class mistake fare for under $500. I got gold with just that 1 trip!

Oct- ~Dec 10 is, in my experience, the most abundant cheap fare period. If you can't find a cheap international MR for this period, you're doing something wrong! :-)

I'm doing YYZ-AMS-HEL/ARN-AMS-YYZ + nested ARN-AMS-LAX-CDG-ARN on skyteam over 2 weeks around US-Thanksgiving for a vacation/MR. Total cost ~3.5 cpm.