CheapAir News

CheapAir Now Booking Flights to Cuba

April 14, 2015

We’re really excited to announce that we just became the first online travel agency to book flights to Cuba for U.S. travelers!

CheapAir Now Booking Airfare to Cuba

UPDATE: On Wednesday, April 15, 2015 CheapAir became the first online travel agency selling direct flights to Cuba for qualified U.S. citizens. Departing daily from Miami International Airport and on a more abbreviated schedule from Tampa and New York’s JFK, this new option is the most convenient and most direct way to travel to Cuba. Havana is accessible via all three U.S. originating airports and Cienfuegos, Santa Clara, Holguin, Camaguey and Santiago de Cuba are all destinations serviced via Miami.

Earlier this year, as part of the plan to lift embargo restrictions, the United States government relaxed the longstanding policy against travel to Cuba and made it easier for U.S. citizens to visit. Since that time, we’ve seen a surge in requests to travel there, so we put our heads together to figure out how we could make the whole process easier for those who qualify.

From a technical standpoint, Cuba creates a big challenge. There are still no airlines that fly from the U.S. to Cuba – either directly or with a connection. The only way to get there, other than a charter flight, is to buy a ticket to a third country like Mexico, Canada, or the Bahamas and then buy a separate ticket from there to Cuba with an international airline that offers service. This is a tedious exercise for a consumer because it requires you to go to separate sites and toggle back and forth in an attempt to piece together an itinerary that will work.

This is the kind of problem our development team loves to tackle. While we couldn’t make the requirement for two separate tickets any less complicated, what we could do is build a system to do all the work for you! Now you can let CheapAir figure out the connections that work from your city and book the separate tickets behind the scenes so you can take care of it all in one seamless transaction! We’re proud of the work our team did to build this in just a few short weeks. That’s something no one else has done!

To be sure, traveling to Cuba is still very different than traveling most anywhere else. First off, and very importantly, it remains illegal for many people to travel there. The government lists 12 reasons for which you are authorized to go to Cuba – journalism, humanitarian work, and to see family members are all on the list. These 12 are the only acceptable reasons. Before making your purchase with CheapAir you will be required to indicate which applies to your travel situation. Unfortunately, a week on a Cuban beach isn’t on the list!

There are other reasons traveling to Cuba at this point isn’t for the faint of heart. See our blog post covering what you need to know about travel to Cuba that describes some of the realities. It’s important to be aware of these challenges.

For now, we are only able to process bookings to the capital, Havana, but we are open to adding other destinations in the future.

All of the limitations notwithstanding, we’re excited to make it easier for those who are authorized to go to Cuba to do so without a lot of confusing and frustrating legwork. We’ll do the heavy lifting so qualified travelers can experience the beauty of the land and hospitality of the Cuban people first-hand.

Havana local


  1. I noticed cheapair does not fly out of a lot of cities like Charlotte, Atlanta, Chicago. What cities, besides NY and LA does cheapair fly out of to Cuba? As per above article, I know it won’t be a direct flight.

    1. Hi Kristina,

      We do offer flights from the U.S. to Cuba through connections in Mexico City. We’re you not seeing any flights? I just attempted a search from Atlanta to Havana and was able to view flight schedules. What specific route are you looking for? I’d be happy to provide you with a link to view flight schedules. Additionally, we’re very close to adding direct flights to Cuba from Miami as well as select days from New York City.

  2. Hello ,How you all doing ? As a Cuban American I want to say thank you for this opportunity, you won’t regret it. Now when I go to the app and type the destination ,it don’t appear Cuba ,its not available on the app ?thanks again.

    1. Hi Lander,

      You’re correct. Flights to/from Cuba cannot be booked on the CheapAir App yet. You must either go online to book or you can call us directly at 1-800-243-2724. Keep in mind, when you purchase flights with CheapAir if the price for the same itinerary goes down any time before your trip, we’ll pay you back the difference in the form of a travel voucher for up to $100 per ticket! Please let us know if you need any help with finding flights.

  3. Hi – we are planning on travelling to Cuba towards to end of August and your site says direct flights yet they all go through Mexico City, are there any direct flights from Miami? Many thnx

    1. Hi Katie,

      Yes, non-stop flights from Miami to Cuba are available everyday… provided the dates you’re searching are not sold out. For a list of non-stop routes and days, you can refer to our blog post here: Please let us know if you have any trouble finding flights.

  4. I want to travel to Cuba from the USA, I will be travelling on an Australian passport. Can you help me do this?
    Thanks … Michael

    1. Hi Michael,

      All you need to do is book your desired flights and select one of the twelve reasons for traveling to Cuba. This is only used for U.S. citizens, but you will need to select one of the reasons. Upon completing your booking, you will receive a confirmation email from us and the Cuban charter company will contact you to review your passport documents and visas to ensure you’re good. Definitely let us know if you need any assistance with finding flights.

  5. I am from South Africa and will be in Florida. What restriction are there for us if wishing to visit Cuba?

  6. I’m planning a trip to cuba . i was born there but I have lived in the US since i was 6 years old. what documents do I need to travel to cuba I’m a US citizen. Please respond by email or call 2032603168. Thanks

    1. Hi Asela,

      You’d need to ensure you have a valid passport, VISA, and a non-U.S. medical insurance. To learn more about what you’d need to travel to Cuba, you can read our blog post here: You’d have to select one of the 12 reasons for your visit at the time of booking. Please let us know if you have any questions.

  7. I am currently in Cuba, i have a visitor US visa. I want to flight direct from Havana Cuba to Miami. Is it possible for me to book this flight?

  8. I want to visit Cuba at the end of August. I am in NY and would like to fly to Havana. I am an educator. I believe that is included on the list of acceptable reasons.I was under the understanding that there was a direct weekly flight from JFK. Now I read that a charter flight is the only way to get there. Please explain charter flights. What day of the week does the flight depart from NYC? I went on the website, provided point of departure and destination and nothing was found. Can you help with hotel accommodations as well? I have a US passport. What else is needed? Thanks.

    1. Hi Maria, Yes it is true that you can fly from JFK or LGA to Havana most days of the week now. We (CheapAir) are the only online travel retailer booking these flights. Take a look at our site to see the options. All direct flights from the States are still charter only (there are no non-stops, except from Miami). Most of the charters from JFK being run by Cuba Travel Services use JetBlue flight crews and airplanes. A few are running using SunCountry, which as you know are both commercial airlines. This i a special case in which they operate “as charters.” If you don’t mind connecting in another country, there are commercial flight options as well. You should look carefully at the days of the week you might want to travel and see what options are available from that day. We do not assist with accommodation, though AirBnB is now booking private rooms in Havana. There are quite a few hotels in Havana as well, but increased demand has made them book up pretty quickly. You will also need a Visa (which our charter partner can assist with obtaining for you) as well as Cuban medical insurance for the duration of your stay. This can be purchased when you land in Havana, though sometimes people do like to purchase that in advance as well.

  9. My father (cuban citizen) needs a flight back to Cuba. He is visiting me. What would be the price for sept 11?

    1. Hi Patricia, Can you share which city he will be flying back to Cuba from? I can’t help you with flights until I know the departure city.

  10. Hello. I am a permanent resident of the USA and I live in south Florida. My dad who is French will be on a tourism tour in Cuba in late october this year and I would like to join him there. Can I fly there using your services?

    1. Hi Eric,

      As long as you are holding a passport from another country and do not have travel restrictions based on your residency status with the U.S., you should be fine. However, we are not experts on foreign nationals traveling to Cuba. If you have any concerns, please reach out to your consulate. As far as booking the ticket, you can definitely do so with us. Best of luck to you.

  11. hi there,
    it looks like most of the flights from miami to havana go thru grand cayman..
    how do i find a direct flight?

    1. Hi there, Great question! So, the one piece of information I’m missing in order to give you the best answer is the dates of travel you’re thinking about. As you know, Cuba is an emerging destination for American travelers and as such, there are some logistics challenges that keep the charter flight schedules less than a well oiled machine. We presently have flights from Miami through October 31st and we are expecting flight schedules to be approved by the Cuban government sometime this week. We are expecting very similar schedules to be available from Miami, but we’re still waiting. If you’re searching on flights that are scheduled to depart from now until the end of October and you’re finding wonky connections, the nonstop flights are sold out. Please let us know if we can help in any additional way. We are curious to hear which category you might fall under (and also, we just want to make sure there is not some sort of technical issue on our site that we might be unaware of – we pride ourselves on a seamless customer experience, but hey! Computers (and people) make mistakes some times. Thanks again for the question.

    1. Yes, of course Adolf. The leisure travel restrictions only apply to US citizens. If you are a foreign national living on U.S. soil, you can travel to Cuba without a special license. However, direct flights to Havana are currently out of Miami, Tampa or New York so you’d need to get to one of those gateways to take advantage of the flights. Hope this helps!

  12. Hello, I’m a German citizen and I’d like first to travel to Miami. at the end of March. After a week, I’d like to visit Cuba. I can’t find any direct flights to Cuba (4/01- 3/04). Can you held me? Thanks

    1. Hi Mel, There are direct flights that will run between Miami and various destinations in Cuba, as well as flights from the NYC area (on certain days of the week). To get an idea of flight times, costs (they will be similar) and schedules you can search for flights in November. Unfortunately, we do not have the updated flight schedules yet for dates in 2016 but they should be coming soon. Apologies for the delay.

  13. Hello,
    I’m cuban and american citizen from Michigan. Is the medical insurance included in the online booking price, or is something else beside the flight ticket?
    Would any direct flight in the future from Michigan?

    1. Hi Humberto, the medical insurance is not included in the price of your ticket, but in most cases (if you book with us) the charter company we contract with will help you get the medical insurance. In any event, even if you were to buy a ticket elsewhere on your own, it is very easy to obtain the medical insurance in Havana when you land. As to your other question, I’m not sure about flights from Michigan. We just added flights from LAX, but I think it’s probably more likely that we’ll see commercial flights opening up and THEN gateways like Detroit will have access. Hope this helps!

  14. Hi have an Italian passport. If I get a visa for Cuba In Italy and fly to Miami can I get a flight into Cuba from Miami?

    1. Hi Daniela, Yes you can. As a foreign national you don’t have any travel restrictions to Cuba. You can book charter flights from Miami using a few entities, including (online).

  15. I’ve booked a tour of cuba; need to travel there either 2nd or 3rd march (both days ok for me). Return anytime from 18th march. Are u able to assist with Direct flights from miami (or Ft Lauderdale) to Havana and back ? I dont want to fly via grand cayman islands!! I will also need a visa (singapore passport holder)..

    1. Hi Shanaka, We should have charter flights to Cuba listed about 30 days prior to departure. The charter company we work with can assist with your obtaining a visa.

  16. I’m a Taiwanese student studying in Florida with only Taiwan (R.O.C.) passport. I’ve hoped to travel to Cuba directly from Miami. However, I was never able to found any direct flights on-line. I suspected my I.P. address (or US network) block me from searching these options! Is that possible? Could I book the ticket with other methods?

    1. Hi there, We sell direct flights from Miami at our site However, inventory generally appears only about one month from travel. If you searched today, you should see some options in December but we do not have January flights loaded yet.

  17. hi, im holding a British passport , i would like travel to Cuba. Do i need a visa.?
    And where i can get the visa?

    1. Hi Teresa, We offer advice mainly to US travelers (who have greater restrictions). The tourist “card” for Cuba is basically issued at the departure airport for a lot of flights incoming to the country, though if you plan on flying in from the US, you’ll need to arrange the card with the company who sells you your ticket. Hope this helps!

  18. Hi. I am a Canadian who visits Florida for the winter, I have friends that want us to meet them in varedero in January 2017 , can we leave Florida and travel to Cuba instead of going back to Toronto to fly from.thanks

  19. Hi, I would like to book a round trip ticket from Mia -Havanna.
    I Have a german passport, can I get the tourist card from you?
    please advise
    thank you

    1. Hi Andrea, When you book your travel through us, the charter company will reach out to you and help you obtain the Cuban tourist card, yes!

    1. Hola Zulay, estas en Venezuela o en los Estados Unidos? Para viajar desde Venezuela no creo que hay restriciones con Cuba.
      Yo recomiendo consultar con la embajada para ver qué documentos de viaje son necesarios para viajar.

    1. Hi Richard, What are the dates you’re thinking about? We can give you a bit more advice if we have some additional detail from you.

  20. Need to go to Cuba to bring a us citizen back to miami for medical attention does this fit into a category for the visa

  21. Hi, My wife and I are Australian Citizens and wish to visit Cuba in December 2016. How do we book flights from Miami?


    1. Hi Dale, Right now we are the only online travel company booking travel from Miami to Havana, but by December things may well have changed. You can also book charter flights from Miami by reaching out to a tour company (there are a few in Miami) who specialize in organizing cultural exchange trips for U.S. citizens. Of course, there are no restrictions for Australian nationals.

  22. Hello,
    I would like to know, As a U.S citizen, do I need to show proof of any (the 12 reasons) when I purchase the ticket Or once I visit the country? if so, what if I travel from another country such as DR, is proof or any other document deeded, visa? Also, can I purchase the ticket (through Cheapair) with multiple destinations to Cuba? like NYC TO DR then to Cuba?

    1. Hi Elena, When you buy your ticket through our website, you will be asked to choose a reason for travel but it is strictly on the honor system. You are not required to show documentation/proof of the reason at booking. It is possible, though not likely, that you could be questioned by U.S. immigration on your return to the U.S. to justify your travel. You do need a tourist card to travel to Cuba and if you arrive via another country like the Dominican Republic without travel restrictions, you will be given the opportunity to purchase a tourist card in the airport.

  23. Hi CheapAir, as a US citizen departing from CA to MEX to CUBA..then back again, and not getting a Passport stamp in Cuba, create a Red flag when returning to the states? As if one was entering Mexico twice but not saying where you went?

  24. Hi,
    I booked my flight from LAX–>Mex–> cuba, i qualify under the sanctions. How can I get a visa? Can i purchase it in mexico or do I need to show it before leaving LAX?

    1. Hi Claudia, You can get the Cuban travel card in Mexico before you board the airplane to Cuba. You can purchase the Cuban health insurance when you land in the country (before you leave the airport). You do not need to do any paperwork to identify the reason you qualify for travel to Cuba, but you should be prepared to discuss it upon your return at customs. Good luck to you!

  25. Hi, I’m an Italian Citizen living in Miami, can I fly directly to Cuba? How do I get a Visa? What is the medical insurance I would need? Where can I get it and how much would it cost? Thanks for your help!

    1. Hi Gino, Yes, you can fly to Cuba from Miami. You can get the Cuban medical insurance in the airport when you land in Havana (for just a few dollars a day). The Cuban tourist card will need to be obtained. If you buy your ticket through us and fly direct from Miami to Havana, our partner charter company will reach out and help you obtain the tourist card. If you fly through Mexico City or Cancun, you will have assistance in the airport to do this paperwork. This is a very interesting time for all of us in terms of Cuba travel. The U.S. and Cuban government have just worked out the resumption of commercial flights into the secondary cities in Cuba (i.e. everywhere but Havana). Havana service is going to be worked out and flight schedules published possibly as soon as August, but certainly by the end of September. There are no restrictions on you as an Italian passport holder (only U.S. citizens have restrictions), so if you can hold out purchasing a ticket until a bit later in the year, you should see regular commercial flights available. Miami will also have flights of course, so you should be able to find an itinerary that meets your needs for a lot less than the charter flights cost right now. Keep your eyes on the news in the next few weeks so you can be ready when the flights come on line. Good luck to you.

  26. Hi, I’m an Australian citizen and we are doing a tour in Cuba we want to fly from Miami to Havana when I look it has drop down box with reasons to visit what should I tick?

    1. Hi Judy, As you are an Australian National this is just a technicality for you. Any box is fine to tick.

  27. I want to ask if I book the tickets to HAVANA on your website from Miami. How can I get the visa because I know your website does not offer the option for visa?

    1. Hi there, in some cases our partner charter company does offer visa (Cuban travel card) assistance. If you email and mention the flights you are considering, they should be able to tell you if it is a flight that will offer visa assistance. Good luck to you.

  28. Hi, I am EU citizen and currently live in USA with US permanent residency status. Can I travel from Miami to Havana and what documents do I need for that. Thank you.

  29. Hello, I am european and I would like to travel to Cuba from Miami(directly) and I have ESTA Visa, and back to USA to after back to Europe, that is possible?

    Thanks in advance

    1. Hi Loretta, Yes. As a foreign national you are not subject to the restrictions that a U.S. citizen would have for Cuban travel.

  30. Hi!
    I come from Poland and I would like to go from Flordia – KEy West or Miami on 18th / 19th January – is its possible?

    1. Hi Sylvia, Yes this is entirely possible. At the moment the only documents you need are those required by the Cuban government (the tourist card and Cuban health insurance). You can buy the Cuban health insurance when you land in Havana (they have a desk at the airport) and it’s just a few USD a day. You can obtain the tourist card on your own before you depart by reaching out to the Cuban consulate in your home country, or you can consult with the airline from which you purchase your tickets (some of the U.S. airlines do have procedures for assisting).

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