Our travel plans for this summer will result in a rather complicated set of ticketing which will probably give the Travel Agent at AAA that robot_grrl should visit in the next week or two nightmares -- or else make their day if they like challenges or get paid by the segment booked.
The first segment that will be needed is a flight for my Mother-in-law from Chicago, or possibly Milwaukee, to San Diego (or possibly Carlsbad or Orange County) in June. Then Tara and I will need tickets to fly from San Diego to Chicago and back for DucKon (flying out on Wednesday evening if possible, back on Monday morning or afternoon).
The fourth segment will be flying my Mother-in-law and Derrick back to Chicago after he ends school a week or so later -- he'll probably miss the last day of school, but that hasn't been 100% worked out.
We won't bother the travel agent about getting to and from Westercon since it will probably be easier, if not cheaper, to drive to Tempe.
The most complicated trip comes next. Tara and I need to fly to Montreal, by way of Chicago. And we need enough of a lay-over in Chicago that one of us can go out through security (carrying only our tickets and the clothing on our back) and get Derrick from my in-laws and fly him on to Montreal. Then we will all return from Montreal together.
Of course the complication is that we have two flights where people who are not on the same round trip will need seats together, and we'll have a round trip to Montreal with a month-long (or longer) lay over in Chicago. I'm 90% sure that a travel agent can work this out. I'd have much less confidence in trying to do this myself.
Of course the other added complication is that, at least from the house, we are almost as close to the Orange County Airport (SNA) as we are the San Diego Airport (SAN) -- at least when you look at road miles without accounting for the traffic volumes between the two metro areas. But for some of the trips, I may want to leave from work, which would require flying out of San Diego even at a less opportune schedule or higher price. Also, I don't think we can easily deal with flying out of one airport and into the other -- since I'm not sure what kind of transport there is between North County and the Orange County Airport.