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Kyle Stewart

1394 Articles

Pittsburgh, PA
Kyle is a freelance travel writer with contributions to Time, the Washington Post, MSNBC, Yahoo!, Reuters, Huffington Post, MapHappy, Live And Lets Fly and many other media outlets. He is also co-founder of Scottandthomas.com, a travel agency that delivers "Travel Personalized." He focuses on using miles and points to provide a premium experience for his wife and daughter. Email: sherpa@thetripsherpa.com
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American Expressamex platinumFounders Card

Founders Card: American Express Platinum With Fraction of Benefits

Kyle Stewart Posted onAugust 4, 2019September 14, 2021 16 Comments
Founders American Express

The Founders Card is a membership card popular with some travelers and is often touted by other bloggers and travel sites. It was time to find out if Founders, American Express Cards are comparable. If you are considering booking travel or signing...

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American AirlinesNews

Contrary to American Airlines Own PR, They Do Penalize Workers Individually

Kyle Stewart Posted onJuly 28, 2019September 14, 2021 51 Comments
American Airlines A330

American Airlines Public Relations contacted me to correct a previous article stating that the carrier was not going after employees directly. Now, there are two examples that this isn’t the case. If you are considering booking travel or signing up for a...

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Travel

Some Southwest Airlines Customers Blind To Shortcomings

Kyle Stewart Posted onJuly 28, 2019September 14, 2021 123 Comments
Southwest

This should be a fun comments section… Any time I write about Southwest, I am inundated with customers who defend their brand. But many are factually incorrect. Is it that they are misinformed or simply unaware of how Southwest...

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Travel

Is Buying United PQMs for Status Crazy?

Kyle Stewart Posted onJuly 28, 2019September 14, 2021 15 Comments
United A320 at gate

When I logged into my United account this week, I found a familiar pitch – buying premier qualifying miles for status re-qualification. Are these purchases a good idea or crazy? If you are considering booking travel or signing up for a new credit...

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American AirlinesNews

CEO Doug Parker Should Fix American Airlines, Not the Market

Kyle Stewart Posted onJuly 21, 2019September 14, 2021 27 Comments
American Airlines A330

Following yet another co-operative op-ed, CEO Doug Parker of American Airlines had time to meet with President Trump this week to discuss Middle East airlines infringing on competition. He should fix his own airline first, not the competitive market....

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DisneyNews

Disney Airline Coming, Best or Worst Idea?

Kyle Stewart Posted onJuly 21, 2019September 14, 2021 25 Comments
Disney

***Disney has since denied any plans to start an airline, however, I am keeping this post active because the ideas explored (should they start an airline) remain valid if they were to start an airline. In the introduction, I...

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Family Travel

Health Care Traveling Challenges Despite Insurance

Kyle Stewart Posted onJuly 21, 2019November 14, 2023 17 Comments
a man wearing a blue cap and blue shirt

Though I have full health care coverage, I had an issue while away from home and I experienced a little glimpse of the nightmare that health care can be while traveling. If you are considering booking travel or signing up for a...

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AmazonNews

Amazon Prime Day Picks: Business Travelers

Kyle Stewart Posted onJuly 15, 2019September 14, 2021 Leave a Comment
Cyber Monday

I travel for work nearly every week and Amazon Prime Day is like my own personal Christmas in July. Here are my picks for business travelers. You will need an Amazon Prime Account to shop the deals, but if you...

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American AirlinesNews

American Airlines Mechanics May Now Be Fined For Declining Overtime

Kyle Stewart Posted onJuly 14, 2019November 14, 2023 62 Comments
a close-up of a person's foot

I have covered the struggle American has had with their mechanics and flight attendants for some time. American Airlines secured a new order from a judge this week that could make American Airlines flights less safe, however. If you...

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Southwest Airlines

Southwest Exclusion of OTAs Costs Business Too

Kyle Stewart Posted onJuly 14, 2019November 14, 2023 24 Comments
Southwest

Southwest Airlines is the only scheduled US carrier that does not make its flights available via online travel agencies (OTAs) such as Expedia or Orbitz. They save money on fees, don’t have to compete side-by-side with all of the...

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American AirlinesNews

American Airlines Suing Mechanics Isn’t Helpful

Kyle Stewart Posted onJuly 7, 2019September 14, 2021 24 Comments
a close-up of a person's foot

American Airlines, in a contract dispute with their mechanics that has lasted years, has decided not only to sue mechanics for a work slowdown but is seeking penalties in a judgment from the courts. But that’s not helping contract...

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News

Toronto Raptors Star Takes Free Jet (Like Drake) To Los Angeles

Kyle Stewart Posted onJuly 7, 2019September 14, 2021 7 Comments
kawhi leonard

Toronto’s hero of the NBA Finals, Kawhi Leonard, didn’t just get the keys to the city, he got a free jet deal from Cargojet akin to Toronto rapper, Drake. Just weeks later, the hero of “the six” moved to...

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Amazon

Affordable Vacation Homes From Amazon Prime?

Kyle Stewart Posted onJuly 7, 2019November 14, 2023 4 Comments
a house with a deck and a patio

It feels like Amazon Prime delivers just about everything these days including tiny home kits. When paired with surprisingly reasonably-priced vacation property, owning a vacation home is more affordable than I would have thought. If you are considering booking travel or signing...

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ChaseCredit CardsNewsUnited Airlines

Banks May Force United, Others To Change Loyalty Programs

Kyle Stewart Posted onJune 30, 2019November 14, 2023 37 Comments
a white airplane on a runway

Airlines are dependent on banks to buy award miles with exclusive credit card deals but at least one relationship (Chase and United Airlines) is struggling. Could this be the moment that airlines reverse course? If you are considering booking travel or signing...

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News

Toronto Raptors Player Gets Drake’s Free Jet Deal

Kyle Stewart Posted onJune 30, 2019September 14, 2021 1 Comment
kawhi leonard

The Canadian rapper, Drake, announced that he had secured a 767 for his personal flying. The deal was likely not as advertised to the public and media’s dismay. Now, Toronto Raptors small forward Kawhi Leonard has one too. If...

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Avianca

Should You Be Worried About Your LifeMiles? They Don’t Think So

Kyle Stewart Posted onJune 30, 2019September 14, 2021 6 Comments
Avianca

LifeMiles, the loyalty program from Colombian carrier, Avianca issued an email this week to reassure members that their miles are safe. But are your LifeMiles safe? I’m not so sure and, clearly, neither is Avianca.  If you are considering booking travel or signing...

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American AirlinesNews

American Airlines Mechanics Making Their Mark

Kyle Stewart Posted onJune 23, 2019September 14, 2021 15 Comments
a close-up of a person's foot

I have written previously about dissatisfied American Airlines employees, recently the mechanics have made the most noise. Now, the results of their actions have begun to show.  If you are considering booking travel or signing up for a new credit card please click...

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HiltonHotelsHyatt

Rollover Credits Move My Remaining Stays to Hilton Over Hyatt

Kyle Stewart Posted onJune 23, 2019September 14, 2021 10 Comments
hotel sign and stranger

This year I have top tier status with several hotel chains but re-qualifying for next year will place an emphasis on Hilton going forward over Hyatt, my focus program. If you are considering booking travel or signing up for a new credit...

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BusinessFamily Travel

Bringing Family On Business Trips

Kyle Stewart Posted onJune 23, 2019September 14, 2021 7 Comments
Mother and daughter walk in Colombia

The more I travel for work, the more I long to have my family with me. But just what does that look like and what are the ethical implications of bringing the family along on business trips? If you...

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American AirlinesElite StatusNewsUnited Airlines

Premium Economy Best Way to Qualify For Status

Kyle Stewart Posted onJune 16, 2019November 14, 2023 15 Comments
United A320 at gate

Last week I wrote about the need for a status run on United to maintain my 1K status. It’s clear that Premium Economy is the best way to re-qualify on seemingly any US airline. If you are considering booking travel or signing...

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