Cheap Flights in the Caribbean: They Exist!

With a new airline popping up in the Caribbean, it's a good opportunity to highlight some of the cheap flights in the region, starting from just $100. I bet you didn't know some of these airlines existed! Also listed are some of the very affordable flights I've seen for such exotic Caribbean islands!

You only have today. Get to know the other islands and create lasting friendships!

Airlines that fly in the Caribbean

Some of these, like Caribbean Airlines are flat out expensive. But mostly these airlines are affordable to cheap. Importantly, these are the airlines that fly within the Caribbean and can help you get to know the neighboring islands and form those relationships!

AraJet

Caribbean Airlines

🔺CapeAir

Air Caraibes

WinAir

Copa Airlines

InterCaribbean

St Barth Commuter

Avianca Frontier

JetBlue Southwest Airlines

Air Antilles 🔺gone out of business!

Spirit 🔺 gone out of business! Silver Airways 🔺 gone out of business!

Updated on June 3, 2026

Flights from $100-$215

These are the most reliably cheap cities to fly to and from. Flights from international airports on the east coast of the US, like Miami, Fort Lauderdale, New York, Atlanta or Boston also tend to have temptingly cheap flights to the Caribbean. But here are the cheapest cities to fly into within the Caribbean:

• SJU Puerto Rico From almost anywhere in the Caribbean, San Juan seemed to have the lowest flight prices, sometimes even under $100!
  

• SDQ and PUJ Dominican Republic

  Flying into Punta Cana (PUJ) and Santo Domingo (SDQ), the DR's capital seems to always be cheap from anywhere! The US, Panama, Puerto Rico, Costa Rica, etc.
  

• SXM St Martin

  St Martin is well-connected. The island has a French and Dutch side, and two airports and ports where ferry's sail from. It's an up-and-coming island.
  

• CUR Curação Ok, so it's not always cheap to fly to Aruba or Curacao, but I was surprised to find that flights to and from the DR to Curação average out to $160 on Arajet! I like Curacao for their good level of Kizomba and UrbanKiz dancing and their unique culture.