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Cheap Flights from Tallahassee to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Montego Bay
Montego Bay1 stop$671
Nassau
Nassau1 stop$653
Saint Thomas Island
Saint Thomas Island2 stops$554
Providenciales
Providenciales1 stop$654
Willemstad
Willemstad1 stop$650
St. John's
St. John's1 stop$761
Montego Bay
Montego Bay1 stop$671
Nassau
Nassau1 stop$653
Saint Thomas Island
Saint Thomas Island2 stops$554
Providenciales
Providenciales1 stop$654
Willemstad
Willemstad1 stop$650
St. John's
St. John's1 stop$761
Booking Insights

KAYAK's insights & trends for Tallahassee to Caribbean Islands flights

Get data-powered insights and trends into flights from Tallahassee to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Tallahassee to Caribbean Islands?

No, with an average price for the route of $409, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Tallahassee to Caribbean Islands?

The cheapest month for flights from Tallahassee to Caribbean Islands is February, when tickets cost $0 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $1,016 and $792 respectively.

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Good to know

Low season

September
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 1% lower on average.

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Tallahassee to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Tallahassee to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Tallahassee to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Tallahassee to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Tallahassee to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Tallahassee to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Tallahassee to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Tallahassee to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Tallahassee to Caribbean Islands

 
Need help choosing which airline to fly with from Tallahassee to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.0
American AirlinesOverall score based on 12179 reviews
7.4Boarding
7.1Comfort
6.4Food
6.8Entertainment
7.9Crew
Airline reviews

Cabin was bone dry, no humidity whatsoever, and pretty warm; and beverage service didn't start for at least an hour. I had to go to the back for water and the FAs tried telling me it was always this way for all Miami flights, which is complete nonsense. Avoid the MAX8 like the plague.

2.0 MediocreTom, Oct 2026
Read more American Airlines reviews

Cabin was bone dry, no humidity whatsoever, and pretty warm; and beverage service didn't start for at least an hour. I had to go to the back for water and the FAs tried telling me it was always this way for all Miami flights, which is complete nonsense. Avoid the MAX8 like the plague.

Im sitting here waiting over an hour for my golf clubs

Flight was 2+ hours delayed and they “misplaced” all 3 of our checked-in bags.

Overall, really good experience, on time and the comfort was there. Wi-Fi was easy to connect

Flight was delayed 5 hours only to be cancelled at 1:30am. I did not get on the rescheduled flight because of worry it would be delayed (which it was). I needed to drive home. Horrible.

When there are many passengers who are going to miss a connecting flight, they always say please let them off first. But the flight attendant never manages that part of the process. It would be helpful if they would repeat that and stress that to the other passengers.

Flight was delayed due to maintenance issue. Missed my connecting flight. Got rebooked in a middle seat when I had a first class ticket.

My boarding pass said gate E5. I arrived at gate E5 by 12:45pm. At 2:10pm, I received a phone call stating I was supposed to be at gate D37. They would not wait for me to get there (by the way, the plane was still there when I got to gate D37, but everything was closed and no one was at the door). The next flight at 7:40pm was sold out; was told I'd be put on the 9:47pm flight. I was so stressed, I became chokey (apparently I have mild asthma). By the grace of God, a lot of begging, and the customer service rep taking pity on me, I was able to get on a 4:50pm flight to Philadelphia.

Comfy and timely flight thanks to Cathay to all crew and the captain for our smooth landing.. above all thank You Lord for our Safe flight ❤️🙌🙏🏽

I left my wallet on flight 2225, no one has reached out to me yet, I field out the form online. Please give me a call Please.

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