Viva Cuba! Part 5 – Flights to Cuba

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Emily:  When I learned about America’s more relaxed policy towards travel to Cuba, I jumped at the opportunity!

Cuba has a lot to offer.  My friends and I were drawn to the classic cars, the Art Deco architecture, and, of course, the friendly people!  We also love music and dance, which is one of Cuba’s specialties! Rick Steves recently produced an excellent video on Cuba that’s fun and informative.

The US and Cuba reached an agreement for direct flights.  Flight availability to Cuba from various US airports and search engines is ALWAYS changing, so be sure to try multiple search engines and cities, if possible.  Readers have reported that some flights to Cuba from the US may be opening up.  When I went to Cuba in December 2015, flights were not scheduled yet. My friends and I flew via Cancun, and continued our journey to Havana.

Note:  Regulations surrounding US travel to Cuba are always changing, so make sure you check the current rules before planning your trip.  There are limited opportunities to use miles & points, but you can save some money.  I’ll show you how later in this series!

Viva Cuba Part 5 Flights To Cuba

Cuba Was Even Gorgeous From the Sky

My travel partners included many of the same friends who accompanied me to Croatia!

Robbie (pink hair) is a professional dance instructor who teaches salsa, kizomba, and bachata.  Sarita is also a dance teacher, as well as a graphic designer.  Gissell teaches fitness classes and loves rock climbing.

On this trip, I went with 3 new friends – Diana, a local art teacher, Chelsea, who manages a hostel, and Antonio, who works in IT design.  Traveling as a group of 7 was fun, but definitely challenging at times!  We had a great time together, and can’t wait to return!

Viva Cuba! Trip Report Index:

Flights to Cuba

Update: Flight availability to Cuba from various US airports and search engines is ALWAYS changing, so be sure to try multiple search engines and cities, if possible.  Readers have reported that some flights to Cuba from the US may be opening up.  It did seem possible to book a flight out of Chicago through  Kayak redirected me to  In this example, you still have to fly through Mexico.

You May be Able to Book a Flight from Chicago to Cuba on Kayak's

You May be Able to Book a Flight from Chicago to Cuba on Kayak’s

However, I tried searching for flights out of Austin, Miami, and Chicago through Google Flights and, but Havana is not supported. I get an error message that says, “Sorry, flights to Havana (HAV) are not currently supported from Chicago (all airports).”

Flights to Cuba Using Google Flights Doesn't Seem Possible Yet

Flights to Cuba Using Google Flights Doesn’t Seem Possible Yet

My Flight to Cuba Back in December of 2015

My friends and I flew from Austin to Cancun, Mexico, on Southwest Airlines.  Booking ~1 month prior to my trip, it cost ~25,000 points plus ~$75 in taxes and fees to fly round-trip in coach on Southwest.  I could have flown for ~18,000 Southwest points if I had chosen later travel dates when the airfare was cheaper, but we couldn’t wait to go!

After flying into Mexico, you will need to take another flight to Cuba.  I booked a Cubana Air flight for ~$350 round trip in coach. In December 2015, this was the fastest and cheapest option available to us.  Again, flight availability is always changing, so check multiple sources before booking your flight.

Viva Cuba Part 5 Flights To Cuba

The Adventure Begins Aboard Southwest

Stopping Over at Playa del Carmen

We decided to stay a few nights in Playa del Carmen before heading to Cuba.

We had a lot of fun in Playa del Carmen, but next time I’d rather spend the extra days in Cuba.  There’s so much to see and do, just in Havana alone!  I was there for 9 nights, and it still wasn’t long enough to accomplish everything on my to-do list!

We arrived in Cancun safely and quickly collected our bags.

Viva Cuba Part 5 Flights To Cuba

Only 1 More Plane Between Us and Cuba!

Once we arrived in Playa del Carmen, we went shopping, tried different restaurants, and gave ourselves a lot of beach time!  My favorite activity was scuba diving in the cenotes, or underground caves.

Viva Cuba Part 5 Flights To Cuba

The Cenotes Were Mysteriously Beautiful

It was soon time to leave for the airport.  We could hardly wait to get to Cuba!  A shuttle bus picked us up at our flat.

Viva Cuba Part 5 Flights To Cuba

I Loved Playa del Carmen, but Was Anxious to Arrive in Havana!

After our short stay in Playa del Carmen, we took a Cubana Air flight from Cancun to Havana.  The total cost to fly coach round-trip was ~$350.  You can’t use miles or points because Cubana Air is not part of an alliance.  I used the Chase Sapphire Preferred® Card card to pay for the flight and earn 2X points on travel.

A Go-With-the-Flow Attitude

We were advised to arrive at the airport 3 to 4 hours before our 4:00 pm departure.  We needed enough time to receive our Cuban visas and check in for our flight.  So we left our flat in Playa del Carmen around noon.

We got our Cuban visas in no time!  Nobody even asked why we were going to Cuba.  We just filled out some personal information on a small piece of paper while we were waiting in line at the Cubana Air counter.

Viva Cuba Part 5 Flights To Cuba

An Airport Worker Distributed Our Visas

After we checked in, we went through security.

Viva Cuba Part 5 Flights To Cuba

Leave Your Jeweled Guns at Home!

And forget about bringing fuzzy handcuffs!

Viva Cuba Part 5 Flights To Cuba

Smoking, Rolling Dough, and Playing Baseball Is Prohibited on the Aircraft

After passing through security, our flight was delayed 4.5 hours.  But we made the best of it!

Viva Cuba Part 5 Flights To Cuba

Eight Hours of Free Time in the Airport Gave Us the Opportunity to Brush Up on the Culinary Aspect of Our Spanish!

The Cancun airport seemed more like a mall with a few restaurants thrown in.  We spent our time shopping and eating!  We received free meal vouchers for the delayed flight.

Viva Cuba Part 5 Flights To Cuba

Dinner at TGI…Viernes?

After being at the airport for ~8 hours, we finally started boarding.  Yaaayyy!

Viva Cuba Part 5 Flights To Cuba

Next Stop – Havana!

After a quick ~1 hour flight, we landed in Cuba.  Then, we waited for our luggage at the carousel.

And waited.

And waited.

Leo (the casa particular employee) told me about folks never getting their luggage, so I was a bit worried.  He advised to pack an overnight bag with necessities for this very purpose.  We still aren’t sure why it took so long, but we imagined 1 guy doing all the work!

Viva Cuba Part 5 Flights To Cuba

Not a Hopeful Sight

Instead of focusing on our delayed luggage, we kept our spirits high, and made new friends with anyone we could find.  We had made it to Cuba, after all!

It was interesting to see some items passing on the conveyor belt.  Many basic supplies are either hard to come by or very expensive in Cuba.

Viva Cuba Part 5 Flights To Cuba

We Weren’t the Only Ones Who Were Tired!

Finally, after 2.5 hours, we all got our luggage!!  It was now ~1:00 am and we were all pretty exhausted after traveling all day.  But we had each other to lean on.  And we were in CUBA!!!

Viva Cuba Part 5 Flights To Cuba

Six Hours of Delays Between Cancun and Havana – and I’d Do It All Over Again!

Our Cuban vacation had begun!  Woo hoo!

You Can Do It, Too!

Link:   How to Transfer Chase Ultimate Rewards Points to Southwest

Link:   How to Earn the Southwest Companion Pass

It’s easy to get to Cuba via Mexico on Southwest Airlines.  Direct flights MAY open up to Cuba in June, so check to see which flights have the least expensive award seats.  Until then, I recommend going through Cancun or Mexico City.

You can get lots of Southwest points by transferring your Chase Ultimate Rewards points to Southwest!  And if you have the Southwest Companion Pass, you can bring a friend for (almost) free!  I also like that Southwest doesn’t charge for checking a bag.

To transfer your Chase Ultimate Rewards points, you must have either the Chase Sapphire Preferred® Card, the Ink Plus® Business Credit Card, or the Chase Ink Bold (no longer available).

You can earn lots of Southwest points by signing-up for the Southwest Airlines Rapid Rewards® Plus Credit CardSouthwest Airlines Rapid Rewards® Premier Credit Card, and the Southwest Airlines Rapid Rewards® Premier Business Credit Card.

Or use the Barclaycard Arrival Plus to erase the cost of your Cubana Air flight!

Bottom Line

You can NOT fly directly from the US into Cuba, but instead must use a gateway city in another country.  My friends and I used Cancun as our gateway city.  We took a pre-vacation trip to Playa Del Carmen while we were there.

We used Southwest points to reach Cancun, then Cubana Air to Havana.  Cubana Air is not part of an alliance.  But you can use the miles you get from the Barclaycard Arrival Plus to cover your flight! 

Lots of things can go wrong while you’re traveling, like flight and baggage delays.  But that doesn’t have to stop you from having a great time!  Learn to go with the flow, and you’ll find the aggravations can make for great stories later!  And to appreciate the positive experiences even more!

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9 responses to “Viva Cuba! Part 5 – Flights to Cuba

  1. This is terribly outdated information. You can already book American Airlines flights from Cuba to the US, and other airlines are likely to follow suit by the end of the summer. You can even book award flights with AA, although you can’t book online. And you can book roundtrip cash flights from Chicago to Cuba for $400, which likely makes a lot more sense than spending miles to get to Cancun then adding another $350 to get to Cuba.

  2. I’d recommend the Mexican carrier Interjet to anyone flying to Havana by way of Cancun or Mexico City. They were efficient, inexpensive, punctual and with surprisingly nice legroom for a budget airline (or for just about any airline these days).

  3. I lead tours to Cuba, so I’m very happy you had a good experience. I wish that you were publishing more updated information. Things are changing very quickly in Cuba, so it is difficult to keep up, but I (and others, I’m sure) would have gladly tried to write more up to date information for you. (Not just on flights, but also in other parts of the guide, such as on wifi, where you corrected the post when someone else pointed out things had changed, but you were originally off by about 6 months in your information.)
    It makes me wonder how much richer an experience you could’ve had if you had more preparation. Our company and, I’m sure the others, sends our people-to-people travelers detailed information on Internet access, packing lists, the problems at the Havana airport (when we can’t have them fly in and out of other parts of Cuba to avoid it), etc., and much of that information is available online. For travelers going on their own, Rick Steves has more updated information in the lecture he recently posted on discussing his December trip to Cuba. Anyone who wants to travel to Cuba, whether on their own rather or with a group, should check out his lecture, which isn’t 100% accurate but contains some useful and more up to date information. (To be clear, I don’t work for him — just trying to provide an additional resource.)

  4. @runtheroad this is info based on her personal experience and what she did. She does say flights are likely to start before the end of 2016.

  5. @runtheroad- Thanks for pointing out that other alternatives may exist. The flights going into Cuba are being added so fast, it’s hard to keep up. I tried searching for flights out of Austin, Miami, and Chicago through Google Flights and, but Havana is not supported. I get an error message that says, “Sorry, flights to Havana (HAV) are not currently supported from Chicago (all airports).”

    It did seem possible to book a flight out of Chicago through, however. I will update the post with this information. But even if I could book that flight back in December 2015, I would not have booked a ticket to go all the way north to Chicago and then back south to Mexico and Havana again.

  6. @ DaveS- Thanks for the recommendation! Hopefully they employ more luggage handlers and are on time more than Cubana Air. 🙂

  7. @A- I’m updating all posts with updated information as I get it from readers, so nothing should be outdated. Please point out any other inconsistencies you may see. 🙂

    I actually did a ton of research for our trip to Cuba (you can ask my friends, I am kind of a research nut, lol). I purchased two guidebooks and scoured the internet for reports on solo travel (most content out there was oriented for tour groups, and we wanted to go to Cuba by ourselves). I printed out about 10-15 articles I did find and used that info for our trip. And actually not having internet access was a blessing because it forced me to connect with people more, so I don’t think I would do anything over if I had the chance.

    For some travelers, I think tour groups can be the way to go if they don’t want to spend time preparing and have the extra money. My friends and I are budget travelers so we had to do it cheap, and we love traveling together.

    For our readers, here is the Rick Steves Cuba video segment: Thanks again, A, for pointing this out! 🙂

  8. Emily:

    I have been really enjoying your series on Cuba and look forward to the rest of the entries.

    BTW, you can also fly to Cuba via Grand Cayman also. Cayman Airways has flights six days a week from Grand Cayman to Havana.

  9. @ Andreas- Thanks for the kind words! I’m so glad you are enjoying it! Thanks also for the Grand Cayman tip. 🙂

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