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If you needed more evidence of the improving relationship between the US and Cuba, just head over to In a statement posted on its website earlier today, the organization claimed that it's just become the "first online travel agency to book flights to Cuba for US travelers" since the embargo came to an end.

However, just because CheapAir is offering tickets doesn't mean it will be easy to get there. Outside of the fact that there are still restrictions for American citizens on traveling to Cuba, there are no US airlines that fly to the island -- neither directly, nor with a connection. So, other than chartering a flight, the only way to get there is by first flying from the US to a third country like Mexico or Canada. Once you get there you'll have to catch a separate flight to Cuba with an international airline. So as you can imagine, this can make trip planning a little complicated. You'll have to coordinate your flights on different websites, with different agencies and different airlines...and that's where things can get messy.

What the development team at CheapAir has done is made the booking process a little easier for you. You'll still have to travel to a third country to get to Cuba, but you can plan the trip and complete the transaction all on their site now. Here's how it works:

First, head to and select the city you're flying from, and the destination as one of the two available cities in Cuba: Santiago or Havana. We're based in Chicago, so we input that as our starting city and Havana as our arriving city. Once you've selected the time and length of your trip, and the number of passengers you'll be taking, click the "Check Flights" button.

From there you'll be taken to a search results page where an itinerary that includes two separate round-trip flights -- one from a US airline that will take you to the intermediate country (likely Mexico, Bahamas, Canada), and then one that will take you to Cuba. All you need to do from there is make the purchase, and you're set to go. Just make sure you're visiting for one of the following 12 reasons, because traveling for tourism to Cuba is still strictly forbidden by the US government.

You can travel to Cuba if you're:

1. Visiting family
2.  On official business of the US government, foreign government, or certain intergovernmental organizations
3.  Going for journalistic reasons
4.  Researching professionally, or attending a professional meeting
5.  Engaging in educational activities
6.  Going for religious reasons
7.  Performing publicly, attending a clinic, workshop, exhibition, or competition
8.  Visiting to support the Cuban people
9.  Doing a humanitarian project
10. Traveling to take part in activities of private foundations or research, or educational institutions
11. Exporting, importing, transmitting information or information materials
12. Exporting certain authorized transactions

Remember -- traveling to Cuba for leisure is forbidden by the US Government, so we suggest you either find a long lost family member to visit, search for an exhibition to attend, or become a humanitarian...because views like this, beaches like this one, and and the pearly white sand here, should not be missed.


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Monday, April 20, 2015 9:50 PM
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