I'm super excited about the fact that travel restrictions to Cuba for Americans have loosened up, and even happier to hear that airlines are offering new flight routes there starting in September... which happens to be the same month I'm planning my visit! I've decided to stop over in Cuba for a week in between a visit to see my family in Michigan and my return to Copenhagen.  

I soon learned, however, that the new flight routes are limited to just a few cities, and they don't seem to be showing up in flight aggregators. So when I looked for a flight from Detroit to Havana in September on kayak.com, the results were disappointing: the cheapest price for a one-way flight was more than $400, with multiple airlines and two stops! The chance of missing a flight or losing baggage felt too risky for me, especially at such a steep price. Come on, I thought, there has to be a cheaper and better way! 

After some digging around and after a lot of research, I was able to book what I think is a better itinerary that's less money and includes an overnight stay in Cancun. If you'd also like to book a flight to Cuba from somewhere other than the new gateway cities in the U.S., here are a few tips based on what I tried: 

  • Search multiple flight aggregators. I am an avid user of Kayak, but it didn't seem to turn up all of the options in this case (possibly because it's U.S.-based and Cuba has been off-limits for most Americans?). I found that Skyscanner and Momondo gave me a few more options.
  • Try searching for separate trips: one to a gateway city and another from that city to Cuba. For example, rather than flying Detroit - Chicago - Cancun - Havana, I ended up booking separate flights: one from Flint (a regional airport) to Cancun, and a second from Cancun to Havana. This option saved me more than $100. Normally travel aggregator sites do this work for you; I think there is something about the Cuba/USA travel restrictions that makes it more difficult in this case. I looked at flights to Cuba from both Canada and Mexico. Obviously your choice will depend on which stopover city is cheapest and easiest for you to travel to.
  • Try flying into cities other than Havana. I ended up booking a flight into Havana, but I noticed when searching for flights from Canada that Westjet flies from Toronto into multiple cities in Cuba, including Varadero. One cool thing about Momondo is that it allows you to select a country as a destination and then shows you which cities you can fly into, which is helpful (just type the country name into the destination search box).
  • Be creative with dates. I ended up booking flights so I have a night's stay in Cancun, because there weren't any flights out to Havana later than 1 pm. That's fine for me because I'm happy to spend a night in Cancun and I figure the money my travel partner and I are saving on the flights will more than pay for the hotel. 
 

Have you been to Cuba? If you have any tips on planning my trip, or where to go / sleep / eat while I'm there, I'd love to hear them!