Another Benefit of TripIt Pro: Southwest Refund Alerts

One of the benefits of the Barclay Arrival MasterCard, a card which has earned a permanent spot in my wallet because of it’s 2.22% cash back on travel, is a free TripIt Pro subscription. To be fair, it’s not really “free” since you pay an annual fee for the credit card, but it would otherwise cost you $49 for a year. I’ve found the app to be exceptionally useful to me over the last year that I’ve used it.

Update, October 2026

TripIt Pro still costs $49 a year and still has a Fare Tracker that tells you when your fare drops after you book (TripIt), but the Barclay Arrival card that came with it no longer exists (see the box below). Southwest has also changed: flight credits created on or after May 28, 2025 now expire, typically one year after purchase and six months for the new Basic fares (University of Colorado travel office), so check your fare type before you cancel and rebook to catch a lower price.

What TripIt Pro Does

The free, non-pro version is nice to have also, but the Pro version sends you mobile alerts about flight delays and cancellations, alerts if you’re eligible for a refund, alternate flight options, and a social “friends circle” where you can get updates on others’ travel plans.

Once you link your email account, TripIt does all the work for you. It automatically pulls the travel emails and logs everything about flights and hotels into your TripIt page. It then monitors everything about your travel, and the part that’s been most useful to me over the past year was the flight delays function. It often alerts me of delays before the airline itself does, assuming they do at all.

One time I was sitting on the plane after push-back and received an alert that my flight was delayed 20 minutes. I thought to myself “hmmm that’s obviously wrong – I’m already on the plane and we’re about to leave.” Lo and behold, the captain announces that there’s a 20 minute delay and we’d be sitting on the tarmac for a bit. Then of course ten minutes later I received an email from US Airways saying the same thing. I was impressed!

Southwest Refund Alerts

I was impressed yet again by the service because of the refund-tracking ability. I have a flight booked on Southwest for September for which I paid $105. I received a mobile alert today saying that I can potentially save $10 because of a price reduction, so I went online to check it out.

For those that don’t know, all Southwest flights are fully refundable regardless of whether you booked with points or cash. That also means that if the price drops after you’ve booked it, you can simply cancel and re-book at the lower price. This TripIt alert was alerting me to exactly that type of scenario. (Alaska Airlines offers a similar benefit, although you only get a credit toward a future flight.)

I went online to check it out and TripIt was right – I could save $10 on my flight by simply re-booking it. If you fly Southwest frequently, I’d say TripIt Pro is worth the purchase price. If you happen to have the Barclay Arrival card, make sure you activate and use the service!

The best news is that it’ll just keep tracking that same flight and will alert me again if there’s a price drop. This is especially useful when Southwest has those relatively frequent sales. On a route like LAX-LAS, there’s a very good chance to get a better price. If you haven’t signed up for TripIt Pro yet, you should definitely look into it.