SKIPLAGGING

Transportation Tech Editor
7 min readSep 25, 2024

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Richard Ramis AYS Dispatch, Inc.

Many years ago, my precinct captain Denny drops in. He needed a favor. He was a regular in our office. In Chicago your precinct captain is your go-to guy. Usually, we would only see him during election season unless we needed something. He would drop off a handful of election posters. He would look me in the eyes and say. “Rich” please get these in the windows quickly. The Alderman will be driving through the ward tonight.

No problem. That is the way the city works, and in those days back yonder the city did work. Then, as occasionally occurs, the day after the election I would get a call from him saying, “Rich”, you know what’s worse than backing a winner? No what. Backing a loser, get those signs out of your windows.

Anyway, Denny drops in one day and asks to see me. It wasn’t election season so who knows. Turns out he needed travel help. Being in the limousine business I had my share of travel agents as clients and friends, so I was happy to help. He explains he must go to the capital in Springfield and since it is such a short meeting it would be easier to fly then drive. He only needed one way as he would ride back to the city with some friends he would see at the seminar. Problem is the airfare was horribly expensive for a 200-mile flight.

Now, I am no travel expert, but I am aware that market not mileage dictates cost. As an example, Chicago to Denver is around 1000 miles but half the cost of Chicago to Des Moines which is just over 300 miles. There are a few reasons, firstly Chicago and Denver are both United hubs, so the flight carries more volume with larger aircraft. Furthermore, both cities being hubs means the flights can be gateway flights which means it is likely many of the travelers are using Denver as a stop to go to California, Hawaii or even the far east.

I used to have these arguments with quoting clients in the day. A customer normally travels from Lake Forest to ORD and that trip was 26 miles and back in the day we would charge about $30.00. Then he calls once because he is attending a wedding in Hinsdale, Il and does not want to drive. Hinsdale is 20 miles from ORD, in the other direction. I quote him $65.00 each way. He completely freaked out. I explain Hinsdale is a western suburb in DuPage County. We would have to drive past ORD all the way to Hinsdale drop. Then go back to the city, ORD or the Northern suburbs empty for our next order.

If he thinks he is smart and calls a West suburban company, he will get nowhere. Although they can drive him from Hinsdale to ORD for a fraction of what I would charge they would clobber him once he mentions Lake Forest. Now obviously when it came to charter work it is a different story. Another twist is the blue-chip downtown Chicago operators who use to (and some still do) charge garage time or portal to portal time meaning the clock starts ticking when they leave the base and stops ticking when they return.

Back to Denny, I call my travel agent Donny and explain the issue. Donny immediately interrupts and asks me, “Does Denny have checked through or carry-on bags?” Remembering what Denny said about only having a short meeting at the capital, I say he has no luggage. Donny starts flipping papers and humming and hawing and after a few minutes declares, tell Denny I can get him out of ORD that day at 719am and it will be $144.00. That price was almost 40% less than he was previously quoted.

I call Denny and give him the news. He loved it, I give him Donny’s number and said glad I could help. Not 20 minutes later Denny calls and says, “Rich are you sure this guy is ok?” I respond, “Yes, what is the problem?” He explains that Donny books him from ORD to DFW with a stop in Springfield. He then informs him that when the plane makes its stop in Springfield, he is to walk off the aircraft. Denny was a little hesitant, but Donny explained he will not be the only one disembarking the plane and he has nothing to worry about.

Folks, this is what “skiplagging” is. It has been going on for years and many frequent fliers who are in the know have been using tricks or perhaps this hack to save money. Only recently the airlines have been starting a major crackdown on this process. And this is not unique only to the airline industry. You have Netflix clamping down on password sharing. Costco going bonkers on membership card sharing. By nature the consumer has learned to game the system and now the system wants to fight back.

Even the mighty McDonalds is not immune from consumer hacks. There are as many web sites devoted to shortchanging McDonalds as there are sites teaching the fine tuning of skiplagging also known as “hidden city ticketing”. Turns out I never realized I was part of the equation way back when. In the very late 70’s early 80’s my second stop on my illustrious career path landed me at Amms’ Limousine Service in Glenview, Il.

It was a breath of fresh air for me. I started at a boutique legacy service in the city and it was simply getting old. The city traffic was a constant struggle as well. Amms was suburban based and the real treat was their service area was Chicago’s North Shore suburbs. Clean, open roads and as high line as they come. Amms was founded in the late 40’s and they were one of the largest services in Illinois. When I started, they were running over 50 Cadillac series 75 factory limousines.

Amms, like many of their competitors, had numerous similar booking rules. The primary one was city versus suburban orders. To have a city livery plate your car had to pass an inspection. The vehicle had an age limit and was inspected annually. The driver had to pass a criminal background check and take a chauffeur’s exam. City orders paid more because everybody charged more since the costs involved were higher. Suburban licensed limousines and cabs had none of this. Fun Fact: a suburban vehicle can legally go to the city from any suburb. Same thing in reverse, they can go from any suburb to the city. Catch is, ORD and MDW airports are in the city.

That is where the first hack was invented. Howard street is the border between Chicago and Evanston, Il. Amms was charging $40.00 for the city to ORD and Evanston was $28.00 to ORD. Well, turns out the border area known as Rogers Park became hack central. Rogers Parkers would order their car with a Howard Street Evanston address. Walk down the block, cross the street and save $12.00. Southern Evanston and Northern Chicago is a very densely populated area and the border along Howard Street is several miles long. Even with a suitcase it made it worth the while.

The next hack the public exploited was changing the pickup times. Amms, like many of its competitors, had time-based price changes. In those days between 1100pm to 500am the price went up $10.00. The consumer figured this out and time permitting would order the pickup for 510am. The night surcharge was more difficult to take advantage of. The key was getting off the plane, finding the nearest pay phone and calling to be dispatched. They based pick up on the phone call not entry in the car. And these people acted like it was a contact sport to beat the system.

Later, when Amms finally started getting stretches some clients learned that drivers were assigned to the same car all the time. By requesting a specific stretch driver but not requesting a stretch you inherited a freebie upgrade.

Everyone has great clientele who understand the provider has an expectation to make money. They are always understanding and easy to manage. However, the smaller element that will pick a fight over a tollway charge really presents a challenge to the hard-working operator. Reminds me years back of the family of five arriving later Wednesday night from Orlando. The flight was delayed due to the snow, and they landed at 1230am. This case was unique. The late charge was a given. The problem was officially landing on fiscal Thursday which happened to be Thanksgiving. Holidays were rate and a half.

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