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Lets Fly Cheaper.com wanted to know some of the leaps and bounds weary travelers will go through to get an upgrade to first or business class, so we went to the source. Former United Airlines gate agent Chasen Richardson was happy to answer some of our questions. Richardson also shares some passenger stories.

1.      How many times a day on average does an economy passenger ask about getting upgraded?

It depends. If we’re including people who are using upgrade certificates or on standby for a complimentary upgrade, then I would be asked about upgrades on every flight. Your run of the mill passenger who books coach on a random carrier on Priceline with no mileage will very, very rarely ask for an upgrade. When they did, they usually wanted to know the price, which was often the full fare difference between what they paid and a standard first class ticket. Requests for a totally free upgrade were even rarer.

 2.      What are some of the excuses they use to get out of economy?

I’ve heard people demand an upgrade for all sorts of reasons. One man was upset that he bought a ticket on Air Canada but was instead crammed onto a regional jet operated by my less than reputable carrier on a 3 hour flight; he insisted first class was the only option to rectify the situation. He was so entertaining I informed the flight attendants that my “manager” said we were to get the man a free drink.

Another guy missed a flight to New York, and was then stuck with a 6 hour layover until the Redeye flight departed that night. The $6,000 first class fare to JFK first class and the $247 fare this man somehow got after spending far too much time on the internet didn’t really seem like a bridge I could gap. About 45 minutes into it, I told him I could get him there an hour earlier on a rival carrier if he would just shut up and leave.

The best demand I ever got was from a man who just sat down in first class from LA, and demanded the same option on the way to Salt Lake City. You see, Mr. Too-many-beers-McGee was booked on a non-stop from LA to Salt Lake City on another airline, but he missed his flight. That airline was nice enough to rebook him onto my airline thru our hub. But our hero decided that as reparation for his dilemma, he would take what was rightfully his and sit in first class. When the count was off, something about our friend made the supervisor and flight attendant decided it was best to just let him sit there and not deal with it. In this first class seat, he was able to have a few drinks courtesy of my carrier. LA gives us the heads up that they didn’t want to deal with a situation, and it was quite literally headed our way. A manager met the plane, and decided to let him continue onto Salt Lake City with a stern warning. When he was denied a legitimate upgrade on the next leg of his journey, he tried again. But this time the airport police decided they had better plans for his evening. He won the battle, but lost the war. Let it serve as a warning to anyone who ever considered simply sitting in a first class seat.

3.      What are the top five silliest things you hear on a regular basis?

The top 5 things that I could care less about are how many miles you have with another airline, how rude another airline employee was despite your obviously apparent charm and sparkling personality, the fact that you were one of 20,000 people that day to fly across the US in a middle seat that day, why this lengthy delay entitles you to a better seat than the rest of the stranded passengers, the fact you paid a fee to check your bag that you seem to think somehow awarded you an upgrade on your next flight, or that you were using gate information printed out 18 hours ago instead of checking the monitors and want compensation for your wasted time at the wrong gate.

4.      Are there any secrets on how a standard economy passenger can win an upgrade or is your airline very strict on allowing just anyone to upgrade?

Most any airline is very strict about upgrades to first class. If the paperwork printed from the computer does not match who is actually sitting in first class, there is going to be drama. The only way you’ll get an upgrade is thru the system, and the only way you’ll get an upgrade in the system is by meeting the requirements for that upgrade, whatever that may be. Sure, there is technically a way around it, but employees would never risk their job for the flying public.

5.      What are some tips and tricks you would advise passengers follow to get an upgrade?

In today’s day and age of computer audits and standby lists that are accessible by the general public, often times the only option for an upgrade is to sign up and let fate take over. But if you are on the list, and it looks possible, it doesn’t hurt to go up and chat with the gate agent, be nice and friendly, and make sure they do something that alerts them to your name and where you are on the list. If you’re not paying attention, and your name is called once, this may be the difference between the seat being held and your name being skipped on the list.

Only check in once. Hovering around the podium or constantly approaching the agent is a sure fire way to hurt your case. Also, being at the gate 30 minutes prior to boarding when standby lists are cleared at most airlines should be common sense, but you’d be surprised how novel of a concept this is for many people. Listen up, and if you don’t get it, don’t take it out on anyone and enjoy the seat you actually paid for. While you can’t expect first, I will say it never hurts to ask about extra economy leg room. The exit rows usually are the last to fill up, and extra legroom sections of economy can be handed out without penalty to the agent in some situations. That is, if they want to give it to you. It’s all about the first impression.

6. Are there any specific airlines you know of that are easier to get upgrades on?

While you have to play by the rules with upgrades, they are much more accessible on some airlines than others. Some low-fare airlines like Sun Country and AirTran allow passengers to purchase often inexpensive first class upgrades right up until boarding time. This is possible on major airlines, but infrequent. U.S Airways often prompts passengers to buy discounted upgrades at check in or before boarding, but most major airlines require a difference in airfare to be paid for an upgrade at the airport. On occasion, airlines like United or Delta will offer a reasonable upgrade at check-in or at the gate, but it is uncommon and you often only have one opportunity.

Hawaiian offers upgrades on the kiosks at check-in, but they are full fare upgrades, only delivered in a more accessible platform than the mainland competitors. Other carriers like Virgin America and American offer a limited number of heavily discounted first class tickets in a fare class between first and economy when you book your ticket.

As always, the best way to secure free first class is to make sure you book all your flights on carriers in one alliance such as Star Alliance or Skyteam whenever possible. Miles build up faster than you think.