I can warn you this question may seem like a minefield.
The most important aspect of the trip is that we are in Vancouver for a long weekend in the middle (Aug 1-3 2014). However we have other options we would like to include:
1) To arrive and spend the weekend in Chicago (ORD) the weekend before(to visit friends). (We would then fly on to Vancouver(YVR) probably on the Monday before the weekend dated above).
2) To drive from Vancouver either to Edmonton or to Calgary. If we drove to Calgary (YYC) it would be with the idea of flying home from there. If we drove to Edmonton (YEG) we would be happy to fly home either from there directly, or drive the extra 3 hours and still fly back from Calgary.
Our aim is to fly most of the long haul flights together. For that, either I need to be in Germany, or my friend needs to be in England, or, if booked with aer lingus, we could maybe both fly to Dublin and meet up there. I have looked at a number of multi-city options and am struggling but determined to find a price under £1000. I'm asking for any suggestions. German airlines e.g. Lufthansa and Condor tend to route flights from bhx - ord through Frankfurt which could be ideal but Condor for one don't fly to ORD. For a return flight FRA - UK or vice versa (booked separately to allow one of us to meet up first and then fly back after) we are looking at close to £100. (Which we could of course split to make it fair)
Any recommendations for airlines, booking websites, travel agents, ticket types etc which you think would be beneficial to our problem would be greatly appreciated.