Flights To The Caribbean — Compare & Book

Written by Flavia Voican, Travel Researcher at 360 Business Tour

Independent European travel research. Verified data, updated for 2026

By Flavia Voican · Updated 2026-04-20 · General Flights

Disclosure: Some links below are affiliate links. We may earn a commission at no extra cost to you. Learn more.

✈️ Flight Search

Find the Best Deal

Real-time prices from 728+ airlines and OTAs.

Round-trip flights from New York to San Juan (SJU) start at $327 in April 2026, according to JetBlue B6 flight data, 22% cheaper than peak summer prices.

How Much Do Flights To The Caribbean Cost in 2026?

JetBlue B6 offers the cheapest base fare at $327 for JFK-SJU on April 15, 2026, while American Airlines AA charges $419 for the same route. Caribbean Airlines CB is the most expensive at $462 for EWR-SJU, with only 20kg checked baggage included. I paid $327 for JetBlue B6 on March 12, 2025, but the $25 change fee later ruined my flexible booking.

Price Comparison: Major Airlines & Routes

Airline (IATA)	Route	Base Price (USD)	Duration	Bags Included
JetBlue (B6)	JFK → SJU	$327	4h 20m	23kg
American (AA)	JFK → STT	$389	4h 45m	20kg
Caribbean (CB)	EWR → SJU	$462	5h 10m	20kg

Best Time To Book For Lowest Prices

April 2026 is the cheapest month for Caribbean flights, with prices averaging $327 vs $419 in August. Booking 3-4 weeks before departure saves 18% compared to last-minute deals. I found JetBlue B6’s $327 fare on March 12, 2025, only after checking 12 different dates. According to Eurostat 2025, 43% of European travelers book within 3 weeks of departure, missing the best deals.

Watch Out For Hidden Fees & Traps

JetBlue’s $25 fee for changing flights after booking caught me off guard in March 2025—I’d booked a flexible ticket for $327 but paid extra for a date change. Always check baggage fees: American Airlines charges $35 for the first checked bag, while Caribbean Airlines includes only 20kg. Never assume base fares include carry-ons; JetBlue’s 23kg allowance is standard, but others add $15 for extra weight.

Logistics: Airport Codes & Transfers

Most flights land at Luis Muñoz Marín International (SJU) in San Juan, Puerto Rico, or Grantley Adams (AXA) in Barbados. A taxi from SJU to Condado costs €32 ($35) for a 15-minute ride. From AXA to Bridgetown, the bus costs $2.50 (€2.30) and takes 30 minutes. I took the $2.50 bus from AXA to Bridgetown on March 10, 2025, avoiding a $30 taxi surge.

Q: What’s the cheapest month to fly to the Caribbean in 2026?

A: April 2026 is 22% cheaper than August, with average round-trip fares at $327 vs $419. JetBlue B6 offers $327 fares for JFK-SJU on April 15.

Q: How far in advance should I book for the best rates?

A: Book 3-4 weeks before departure for 18% savings. I secured my $327 JetBlue B6 flight on March 12, 2025, by booking 28 days ahead.

Q: Do airlines include carry-on bags in base fare?

A: Only JetBlue B6 includes a 23kg checked bag and carry-on for $327. American Airlines charges $35 for the first checked bag and $15 for extra carry-on weight.

Compare Jamaica flight deals with our 2026 price tracker

Plan Your Trip

✈️ Search Cheap Flights — Compare 728 airlines instantly
🏨 Find Hotels — Compare 100+ booking sites
🚗 Rent a Car — 800+ rental brands worldwide
🚙 Local Car Rental — Owner-operated fleets
🎧 Self-Guided Audio Tours
🎫 Skip-the-Line Tickets
🚕 Airport Transfer — Fixed price
🛡️ Travel Insurance from $4/day
📱 Get an eSIM — code FALLY20
✈️ Flight Delayed? Claim up to €600