How to Outsmart Aeroplan and Get Good Vegas Flights

I'm cheap. I don't come from good family stock. Our family portrait was done by a courtroom sketch artist.

But I did learn a few critically important things about life from my beloved parents, things which I've essentially ignored, and gone my own way.

And some of what I've figured out on my own is how to work the angles on points, comps, and rewards.

First rule of booking Aeroplan (or any reward) flights. Book Way Ahead.

With my astronaut training complete, we're have a launch window for a mission to Vegas next month - so that one is out the window.

Second rule of booking - book non-stop flights.

Most people would use the Aeroplan site and their horrible search engine, find something that matches the points they have, and book.

I can almost guarantee that they'll be on the late evening flight out of Toronto, getting to Vegas as late as 2:00 in the morning, Eastern time. If they are extremely lucky, some might score the morning flight.

I can almost guarantee that they'll be on a redeye for the return and both of these trips will be on Slaveship Rouge.

Having to connect from Flusherville makes it that much more difficult - I can't get to Toronto in time to get the morning flight.

I figured there has to be another way.

Third rule of booking - look for alternative routes on partners.

This is where Jimmy Poon put his tech-savvy 'internet' skills to use. We sat down and started digging.

First we looked at Aeroplan itineraries. They all sucked, unless you relish a trip with stops in Toronto, (where you'll overnight in the lovely terminal building), Vancouver, L.A., and then on to Vegas for a total travel time of 26 hours.

Here's a sample itinerary that leaves Flusherville at 8:45 in the evening for Toronto, where you sit around until half an hour past midnight. Then you fly to Montreal, arriving at 1:45 am. Then you wait until 6:15 am for your flight to Vegas, which arrives at 10:33 am, leaving your fresh as a daisy, and ready to start you casino exploits.

Dear God.

Why would Aeroplan even offer such a hell-ride?

Next, Jimmy Poon dug out the big guns to try something we'd never tried before.

Air Canada partners with United. And, if you can find reward flights on United, you can book them by calling the Aeroplan number and providing the itinerary (and pay an extra thirty bucks or so for the privilege).

By flying through Chicago or Denver, I could possible catch United metal for one or both legs out of Toronto. It would be an extra stop (breaking Rule One) but it might mean I could leave Flusherville in the morning, and arrive in Vegas at a reasonable hour. Like dinnertime.

Jimmy Poon made use of the United site, and also logged into my sister Divana's Expert Flyer account. Divana doesn't actually use it - she pays, and gets Jimmy Poon to dig deep flight info on it on her behalf.

Amazingly, two hours, 59,000 mouse clicks, and 319 open tabs later, we had an itinerary that was beautiful. We even had a couple of backups. Both United's site and Expertflyer showed available reward space.

I phoned Aeroplan and started dictating my wants.

Denied. The answer kept coming back 'that flight's not available'. Over and over. I confessed what I was up to and the reason was simple, and yet had eluded my pea brain and Jimmy Poon's Brainiac brain.

Award space on United IS NOT THE SAME as reward space on Air Canada.

Fourth rule of booking Aeroplan - take your lumps and book a shit itinerary because you didn't follow the First Rule.

Completely defeated, I sent Jimmy Poon home and went to the Aeroplan booking site.

Comparing my hotel offer dates against the available flights... I found something that worked.

I'd be on the late evening Slaveship Rouge flight to Vegas, the one that is always delayed, and the one that gets me to the casino at 3:30 am.

But at least... I'M GOING! And, with a preferred seat upgrade added, it's only costing $178 CAD bucks return.

The best part? I managed to find a return flight that is NOT a redeye and is NOT on Slaveship Rouge! The penalty? An extra stop in LA. But I will arrive home like a civilised, broke, exhausted gambler

Not as an uncivilised, broke, exhausted, sleepless, gambler.

With that set, and with a pretty good idea of my casino offers, the next step is to find those comped rooms, and maximize the freeplay and other goodies.

---

Addendum: The basic approach described to book partner flights is still sound. I just missed an important step. Essentially, you use the partner airlines booking site and/or Experflyer's search engine to locate flights that work for you and that have award space. The thing I didn't do is to use Aeroplan's  booking tool to check each leg separately for availability. Then you call in and book, providing the flight numbers to the agent. If I ever have enough Aeroplan Fuck You Points to do this again, I'll give it a spin - booking early this time.