[Expired] [Deal Alert] New York to Tobago From $424 Round-Trip

Updated: May 19, 2026, 9:40am CDT

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Fare Deal — Details
How To Book
Final Thoughts

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Update:The offer mentioned below has expired and is no longer available.

We rarely see nonstop flights to the Caribbean island of Tobago, so this flight deal for under $500 round-trip caught our eye.

Let’s take a look at how you can save on an upcoming flight!

Fare Deal — Details

This deal is operated by Caribbean Airlines on a Boeing 737 MAX 8 jet from New York (JFK) to Tobago (TAB).

BW JFK TAB — Image Credit: Caribbean Airlines

Tobago is a small island in Trinidad and Tobago, known for its pristine beaches, music, and food. Several airlines, such as JetBlue, offer nonstop flights to the main airport in Trinidad, Port of Spain (POS). However, Caribbean Airlines is the only airline that offers nonstop flights from the U.S. to the smaller island of Tobago.

Play with some dates on Google Flights and book directly through the airline or an online travel agency (OTA) like Expedia. You may find cheaper tickets using lesser-known OTAs. However, if you want more peace of mind, book your ticket with a more reputable option.

Class: Economy
Routes: New York (JFK) to Tobago (TAB)
Dates: September 2024 to November 2024
Rates: As low as $424 round-trip

Hot Tip:

Caribbean Airlines unbundles fares to keep prices low, as the cheapest tickets include a seat on the flight and virtually nothing else. If you want more flexibility to check bags or pick your seat, you should upgrade to a more expensive fare.

How To Book

The cheapest availability can be found in September and October 2024, though other dates are also available at a slightly higher price.

Either way, you’ll want to book your tickets with a travel rewards credit card. Here are a few of our favorites here at Upgraded Points — all of which offer sizable welcome bonus offers and elevated earnings on flight purchases:

Platinum Card^® from American Express: 5x Membership Rewards points on flights booked directly with the airline or through AmexTravel.com (capped at $500,000 spent in purchases per calendar year, then 1x points)
The Business Platinum Card^® from American Express: 5x Membership Rewards points on flights booked through AmexTravel.com
Chase Sapphire Reserve^®: 8x Ultimate Rewards points on all purchases through Chase Travel; 4x points on flights and hotels booked directly
Chase Sapphire Preferred^® Card: 5x Ultimate Rewards points on flights booked through Chase Travel; 2x points on all other travel purchases

Final Thoughts

This certainly isn’t a deal we see every day, so these cheap flights to Tobago were a welcome surprise. Tobago is one of the most gorgeous islands in the Caribbean, and now you can fly there for under $500 round-trip.

But hurry, such cheap deals likely won’t last long!