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Hand-picked deals by our pirate team

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Hand-picked deals by our pirate team
TravelPirates
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TravelPirates

Hand-picked deals by our pirate team

Get inspired!

Hand-picked deals by our pirate team
Caribbean, old San Juan, Puerto Rico
This deal is already a few days old and availability may have changed.
Flights

Nationwide Flights to San Juan, Puerto Rico 🌊🐠

Fly to San Juan from $166 Round Trip on Legacy Airlines & JetBlue—Usually $450+

From $166

Published by
Eduardo Vega·3/7/2025
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Pirates, we've found some incredible prices on Legacy Airlines & JetBlue flights to San Juan, Puerto Rico. Usually, you would pay $450+ on these flights, depending on the departure city, but you can book them today from $166 round trip.

🏴‍☠️ Pirate Insight: US citizens do not need a passport to enter Puerto Rico, but we still recommend that everybody gets a passport to keep their travel horizons open.

Highlights

Great for Couples
Great Food

Departure

  • Orlando
  • New York City
  • Boston
  • Los Angeles
  • Austin
  • Chicago
  • Washington
  • Tampa
  • Fort Lauderdale
  • Raleigh

Destination

  • San Juan
  • Caribbean

Details

Here are some of the dates and departure airports we found for you, but many more are available.

These fares are based on short layovers or nonstop journeys.

All prices listed are from Legacy Airlines and JetBlue; there is more (and lower) price availability on other airlines like Spirit & Frontier, but often the amount you pay in the end can come out to be more depending on what "extras" you need.

*Note: You might need to scroll down to find the prices with these airlines.

🔻 Departing from Fort Lauderdale

🔻 Departing from Miami

🔻 Departing from Philadelphia

🔻 Departing from New York

🔻 Departing from Raleigh

🔻 Departing from Cincinnati

🔻 Departing from Indianapolis

🔻 Departing from Houston

🔻 Departing from St. Louis

🔻 Departing from Nashville

🔻 Departing from Tampa

🔻 Departing from Westchester

🔻 Departing from Orlando

🔻 Departing from Charleston

🔻 Departing from Boston

🔻 Departing from Chicago

🔻 Departing from Toronto

🔻 Departing from Los Angeles

Example of Cheapest Flight

How to Go Past Those Low-Cost Airline Rates

  1. On the left side of the screen, click where it says "AIRLINES" to expand and see the lowest prices from each airline.

  2. Select the Legacy Airline with the lowest price, or whichever works best for you.

  3. That's all.

Other Options

Also looking for a place to stay? Try our Hotel Booking tool.

Additional Information

All of our deals are available at the time of publishing, but prices are subject to fluctuations and changes at any time.

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