Southwest Companion Pass Will Take You to Costa Rica!

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Southwest will begin flying to Costa Rica March 7, 2015!  This is especially great news for folks with the Southwest Companion Pass.  Because the Companion Pass allows you to bring a companion on your flights for nearly free!


The View From the Costa Rica Marriott Hotel San Jose in Costa Rica

The Southwest Companion Pass is the best deal for domestic travel and it’s becoming 1 of the best deals for international travel to destinations just south of the US like Mexico.  I’ll explain!

Visit Costa Rica and 5 Other Countries With Southwest

Link:   Southwest Credit Cards

Link:   Chase Sapphire Preferred

Link:   Chase Ink Plus

Link:   Chase Ink Bold

Southwest will make daily round-trip flights between Baltimore Airport (BWI) and to San Jose, Costa Rica to Juan Santamaria International Airport (SJO).  Flights begin March 7, 2015.

I excitedly checked the Southwest website to see if I could book a flight, but Costa Rica isn’t in their system yet.  They’ll be sold when the Department of Transportation gives their official stamp of approval.

Emily and I love our Southwest Companion Pass because she can fly with me to any Southwest destination for nearly free!  We’ve mainly flown Southwest to visit family and friends in the US.  But now we’re tempted to take more trips south!

Outside of the US, you can fly Southwest to:

  • Aruba
  • Bahamas
  • Costa Rica (flights to San Juan begin March 7, 2015)
  • Dominican Republic (flights to Punta Cana begin November 2, 2014 pending approval)
  • Jamaica
  • Mexico (Cancun, San Jose del Cabo/Los Cabos.  Flights to Mexico City begin November 2, 2014)

What If You Don’t Live Near Washington, DC?

You should be able to book connecting flights to Baltimore (BWI).  But if you can’t you have other options.

You can transfer Chase Ultimate Rewards points from your Chase Sapphire Preferred, Ink Plus, or (no longer offered) Ink Bold to British Airways.

Folks in other parts of the country may consider using their Southwest Companion Pass to get to Costa Rica or using British Airways points to get to the Washington, DC, area.

You can get Southwest points with the Chase Southwest credit cards.  I suggest waiting until the cards offer a 50,000 point sign-up bonus.

Bottom Line

Southwest will begin flying to Costa Rica on March 7, 2015, with direct flights from Baltimore (BWI).  Costa Rica will be the 6th country outside of the US you can travel with Southwest.

This is exciting news because the Southwest Companion Pass allows you to bring a companion on your flights for nearly free!

Read more about how to earn the Southwest Companion Pass to get Big Travel with Small Money in the US, Mexico, Caribbean, and Central America!

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10 responses to “Southwest Companion Pass Will Take You to Costa Rica!

  1. Even IF they are approved for Costa Rica, I won’t be using southwest to get there. Even though we have the companion pass, the flight will probably take 14 hours from Dallas. First you will have to go to BWI and with SW that means stopping at at least 1 or 2 cities along the way, it’s like riding the bus. Using Avios on our upcoming flight to Jamaica seems wasteful since we have a companion pass with SW, but SW would take 7 hours+ to get there, where a direct flight on AA takes only 3 hours. Dallas will finally get nonstop in Oct. but checking the schedule there are very few. For example out of 20 flights from DAL to LAS 3 will be nonstop and of course they are at a premium price.

  2. From upstate NY, this works for me. I was hoping to book a trip to Costa Rica in the spring so this might work perfectly since I would only need a one-way.

  3. Daraius–do companion pass benefits apply at the time of booking or at redemption? For example, if my pass expires in December and I am making a booking for February in November, can I apply companion pass benefits? Thanks!

  4. Carribean explorer

    Be sure to check your shots before going to CR…. 😉 *tic (as per Drew’s recent bizarre tell-all at TIF)

    As a thought Daraius, just as in the past when you did us a great service with your series on domestic car rental pointers and strategies, perhaps you could do a series in the future on things to know about travel to the Caribbean…. including things like passports, required shots, car rentals, airport/customs waits, and local tipping/extortion traps to avoid….

    Am thinking to use our companion pass to do Jamaica, Cancun & Aruba myself soon….. yet confused as all get about potential car rental nightmares in such places. Was also not impressed to hear SWA rep. warn me about need to get to the Cancun airport 3-4 hours before depature…. (which ruins thoughts to do a weekend getaway there…. Is it really THAT bad?)

  5. Carribbean explorer

    ps to wise2u, not sure I follow your lament…. of course it would be absurd to fly from Texas to Baltimore to get to Costa Rica…. But for those close to the major BWI hub for SWA, it’s got great potential.

    But caution for everyone….. if you’re starting from an SWA airport not currently set up to handle/ticket international departures, you’ll have to have two separate itineraries to go international…. when you get to BWI, you then would need to get your bags, check OUT through security, then go to the ticket counter, get your international boarding pass (you have to show your passport), and THEN go back through security!!!!

    Currently have to go through this serious two-step dance when flying out of Richmond, VA to points south…. (and I can connect nicely through ATL or MCO – Orlando – gateways, except for the lag of the two step….)

    Yet SWA has been adding more of the smaller market airports as international departure points…. as of Dec. 16th, even RIC gets added. (and the fares to places like Jamaica are really attractive….. so far…. yahoo!)

  6. Why can’t SouthWest fly direct out of the Miami/FLL area like Spirit and American already do successfully? Maybe the FLL/ICE administration has some requirements that need to me met, but nothing is impossible — it makes not a whole lot of sense for the vast majority of folks to fly first to ATL or BWI, and then back South to SJO/CUN/PUJ/MBO etc.

  7. I booked miles/companion pass to Jamaica from Chicago over Thanksgiving weekend total cost for fees/taxes $200. Planning on taking a taxi to resort.

  8. Hi, can we still sign up for sw plus and premium each at 50k bonus?
    Also, can we churn these cards at all?

  9. I have found from looking that many flights are disappearing from old Airtran routes The Bahama routes from a major city in Texas, San Antonio, are disappearing in 2015, along with very few flights during the month to Aruba and Jamaica …..and Bermuda has just disappeared. It would never make sense to go anywhere from TX to CR by way of BWI, my only way to go SWA to the Bahamas. Outside of MX, we here in South Texas have a long limited amount of routes to the Caribbean.

    Southwest is not turning out to have all the value of Airtrans.