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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$670
Saint Thomas Island
Saint Thomas Island2 stops$493
Providenciales
Providenciales1 stop$694
Willemstad
Willemstad1 stop$650
St. John's
St. John's1 stop$761
Montego Bay
Montego Bay1 stop$671
Nassau
Nassau1 stop$670
Saint Thomas Island
Saint Thomas Island2 stops$493
Providenciales
Providenciales1 stop$694
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

October
Best time to beat the crowds but there is an average 7% increase 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 12194 reviews
6.4Food
7.9Crew
7.4Boarding
6.8Entertainment
7.1Comfort
Airline reviews

Good flight, excellent personnel; poor comfort, small seats, big cost.

10.0 ExcellentMA, Oct 2026
Read more American Airlines reviews

Good flight, excellent personnel; poor comfort, small seats, big cost.

This trip on American was the WORST I have ever experienced. The plan was LATE taking off from Tucson due to mechanical issues. It caused me to arrive late in Dallas, so I tried to move flights so I would not miss my dinner meeting. First attempt, that flight was delayed, Second attempt, that flight was also delayed. Got back on original flight, the mechanical issue was NOT fixed, so we de-planed and had to find the new gate. Overall, was which was 4 hours delayed and missed the dinner meeting. Friday return, flight from Orlando was on time and landed early. Then the next flight was delayed due to crew coming in late, and them waiting on other passengers. After 90 minutes of delay, we boarded, and then were informed the Fist Officer could not fly due to time constraints. At 12:15 AM we were offered a hotel for a 4:20 boarding flight. Not happening. DFW was COLD and no place to sleep. Plane delayed again to 6:50, but was late taking off AGAIN. Finally landed in Tucson at around 8AM. Should be refunded 75% of the ticket costs due to negligence, nothing more.

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.

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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