Saving Over $500 on Flights to St. Kitts and Puerto Rico

*scroll down to see how I booked a $600+ flight for only $71*

I’ve got an upcoming trip to St. Kitts and Puerto Rico and I couldn’t be more excited! My friend is in vet school at Ross University on St. Kitts, and she offered me a place to stay for the week when I visit. How could I pass up the chance to visit a friend I’ve only seen once or twice since graduation, while staying with her on a tropical island?!? I’ve been thinking about taking this trip ever since I knew she was attending vet school there, but then cross country moves and other travel got in the way. I also had to contend with her jam-packed schedule of studying for exams and doing homework – didn’t want my visit to cause her to do poorly on a test!

Initial Research

Since lodging was already taken care of, I just needed to figure out how to get there. All of the flights I could find ranged from $500-700+ which is waaay out of my budget. So I looked into what airlines fly to St. Kitts. One great resource for that task was At that website, you can enter the departing and destination airports and they tell you which airlines fly between those locations. It was helpful to get an idea of what airlines fly to St. Kitts without having to browse through multiple airline websites.

I found that American Airlines, US Airways, Delta and Air Canada appeared to be the primary airlines that flew to St. Kitts – but most of them were not direct flights, and some of them were not available from my nearest airports. But I did notice something interesting while looking at the flights – they primarily connected through Miami, Florida or San Juan, Puerto Rico.

The need for a connection got me thinking – why not do a layover in San Juan? I’ve never been to Puerto Rico, so it’ll be a new adventure! So of course then my next step was to look for direct flights to San Juan. Luckily, Airtran flies from my preferred airport (Baltimore, Maryland) direct to San Juan.

My next step was to figure out how to pay for all these flights – there is a reason why I have primarily focused on Airtran and American Airlines so far.

Paying for Flights

I received the Chase Sapphire Preferred credit card early this year, when the signup bonus was 50,000 Ultimate Rewards points. Due to the structure of UR points, I can transfer them 1:1 to partner airlines, which include Southwest, British Airways, and United.

Notice that none of those airlines were mentioned in the lists of flight options above? Here comes the best part.

  • Southwest has merged with Airtran. I can transfer points between the two rewards programs with no penalty.
  • British Airways has airline partners for routes they don’t serve (this will be critical when booking our flights to Europe, more on that in a future post). I can use BA points to book flights on their partner airlines, with no penalty.

Baltimore to San Juan

  1. So my first step was to transfer 19,000 UR points to Southwest (I had a couple hundred in the account already).
  2. Once they posted to the account, I transferred 19,200 points to Airtran to get 16 credits.
  3. Using those credits, I booked a round trip flight from Baltimore to San Juan. It cost me about $5 out of pocket for fees.

San Juan to St. Kitts

But that only got me to Puerto Rico! I still needed to island-hop to St. Kitts! Enter American Airlines and their partnership with British Airways. Since British Airways is distance-based when it comes to booking award flights, I knew I needed 9,000 points for the distance between San Juan and St. Kitts.

  1. I transferred 9,000 UR points to British Airways.
  2. Using those points, I booked a round trip flight from San Juan to St. Kitts. This part of the journey was a little more expensive, at $66.

It did allow me some freedom in choosing my schedule, so I tacked on two nights in Puerto Rico after my trip to St. Kitts. All I had to do was book the flights at the dates/times I wanted, since I wasn’t trapped by booking on one airline, where they normally do not allow multiple-day layovers.


In short, I booked a $600 flight for $71 plus 28,200 points. Some travel bloggers are concerned about maximizing the “dollars per point” they can get – so they advocate flying in Business or First class. But really, I don’t need that. I just want to use my points to take me places I wouldn’t be able to afford to go on my own. I’d rather use fewer points on booking a flight, and fly coach, if it means I have points left over for a future trip somewhere exciting!

The way I did it required a little more coordination (since I am flying two different airlines), but I could have made it simpler if I wanted to spend more points. I could have taken an American Airlines flight to San Juan and then continued on to St. Kitts, but it would have required significantly more points (I think the total would jump from 19,000 points for Airtran vs. 25,000 points for American on this leg of the journey). Since I’m in no rush, and I am inconveniencing only myself, I took the tradeoff of more coordination to save some points for future travel. I can’t wait!!

Categories: Credit Cards, Planning, Puerto Rico, St. Kitts, Transportation

Tags: , , , , , , , , , , , , , , , , , , , ,

3 replies

  1. Hey There. I discovered your blog the use of msn. That is a very well written article. I will be sure to bookmark it and come back to read extra of your helpful info. Thanks for the post. I’ll definitely return.


  1. Free Flights on AirTran – Caribbean Part 2? « wander one day
  2. How I Almost Lost 40,000 AAdvantage Points « Wander One Day

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