Reader Mike asked,

I’ve booked myself a flight to Hawaii but having trouble finding a good one home in F. I’m looking at AS,AA & UA since I have points for all & UA seems to have the most options in general, just not to MSP. My idea is to do separate award searches to one of the hubs, then from the hub to MSP and see what I can find. If I do find something, can I call United to feed the agent segment by segment, even if the website does not list my proposed itinerary as an option when searching HNL to MSP? .

Simple answer: Yes

Mike is asking about a very important principle in award search.

1. Airline computers are pretty limited in what they’ll search for you. They will come up with some of the obvious connections but certainly not all of them.
   
2. Airline agents are widely varied in skills, and aren’t incentivized to be helpful. They don’t get bonused based on successful awards booked. If anything they may be docked for spending too much time on your needs.

So you need to put together award itineraries yourself. And much of the time those itineraries aren’t available for booking on your airline’s website. They often don’t show up when the agents search, either.

Start with the hardest segment, which is usually (although not always with Delta…) the overwater segment. Then worry about getting to the international gateway city if a connection is needed, and from the international arrival city to your destination.

Write down the flights you want and then call.

Bear in mind that agents hear people asking about awards all day long and usually find nothing available. Agents are also skeptical that you will find things they do not. They may even tell you they “have to go by what the computer says” when you enter an origin or destination city.

• Just ask about the first flight in your itinerary, if it’s available. “Great, now that we’ve found that, can we check _______.”
  
• I find it’s easier to suggest that a previous agent found available flights for me, rather than explaining I found them on my own (they’re likely to think that I simply searched for revenue flights and that I don’t understand award availability).
  
• Once flights you mention start coming back availability you’ll turn around the agent’s expectations, and they’ll generally be easier to work with.
  
• If I get an unhelpful agent, unwilling to search segment by segment, hang up and call back.