How do you get free bags on Southwest now? How about Southwest alternatives? And is the Southwest Companion Pass still the best deal out there? On the this debut episode of Upgraded Points, expert travelers Katie Corrigan Seemann and Christopher Hassan answer these questions and more to help you get the most bang for your buck when you travel.

Katie and Chris start by discussing their recent travels — Chris recently stayed at the best resort in Orlando for families, and Katie visited Palm Springs and La Quinta. Next, Katie and Chris discuss recent changes to Southwest’s policies, most notably ending its policy allowing travellers to check two bags for free. Learn how to navigate these changes and travel like a pro!

For detailed show notes, navigate using the time stamps below: 

[0:43] Chris just got back from Orlando, where he stayed at the Conrad, which is a part of the Evermore Resort. He says the Conrad might be the best family resort in Orlando.

[2:00] The Conrad is a Hilton resort, and staying there 90,000 points each night. Chris and his wife also got $400 off through their Amex cards.

[3:19] Katie recently stayed at The Hyatt at Palm Springs, where she used free night certificates. Afterwards, Katie went to La Quinta, which is about forty minutes away. She stayed at La Quinta Resort & Club.

[7:07] Southwest is making some big changes. For one, travelers will earn less points with their paid fares. 

[8:20] On May 28th, Southwest will be removing their two free checked bags. Points will begin to expire after a year, and the value of those points will fluctuate. 

[11:23] There are still ways to fly with free bags on Southwest. Starting on May 20th, you can get one free checked bag if you are an A-list member or a Southwest credit card holder. 

[13:58] Through June 30th, you can get an A-list status match on American Airlines for four months. On Delta, you can get a status match to gold or platinum medallion for Southwest A-list and A-list preferred members respectively. The Delta matches last until September 30th.

[16:17] As of right now, a majority of travelers will get the best possible deal from the Southwest Companion Pass, which allows you to add an additional traveler for only the cost of the additional taxes and fees. However, Katie thinks that the companion pass is likely to change.

[18:45] Moving on to audience questions, one reader asks about booking on Japan Airlines. Chris recommends using alerts to catch the best deals. 

Want more out of your points? Explore our guides written by travel and financial professionals on the Upgraded Points website.

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