$107 Find Cheap Flights from Tallahassee to Caribbean Islands - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Tallahassee to Caribbean Islands departing on 9/22. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Tallahassee to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay2 stops$467
Nassau
Nassau1 stop$457
Simpson Bay
Simpson Bay1 stop$657
Providenciales
Providenciales2 stops$718
Bridgetown
Bridgetown1 stop$722
George Town
George Town1 stop$631
Willemstad
Willemstad1 stop$630
St. John's
St. John's1 stop$659
Montego Bay
Montego Bay2 stops$467
Nassau
Nassau1 stop$457
Simpson Bay
Simpson Bay1 stop$657
Providenciales
Providenciales2 stops$718
Bridgetown
Bridgetown1 stop$722
George Town
George Town1 stop$631
Willemstad
Willemstad1 stop$630
St. John's
St. John's1 stop$659

Book Cheap Tallahassee to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Tallahassee to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Tallahassee to Caribbean Islands

Tue, Oct 20 - Mon, Oct 26
Multiple Airlines Logo
3:52 pm - 11:38 pmTLH  Tallahassee-SJU San Juan Luis Munoz Marin Intl
7h 46m1 stop Fort Lauderdale
Multiple Airlines Logo
5:12 pm - 10:30 amSJU  San Juan Luis Munoz Marin Intl-TLH Tallahassee
17h 18m1 stop Fort Lauderdale
$208Multiple Airlines
Tue, Oct 20 - Mon, Oct 26
Multiple Airlines Logo
11:10 am - 8:44 pmTLH  Tallahassee-SJU San Juan Luis Munoz Marin Intl
9h 34m2 stops Raleigh-Durham Orlando
Multiple Airlines Logo
5:12 pm - 10:30 amSJU  San Juan Luis Munoz Marin Intl-TLH Tallahassee
17h 18m1 stop Fort Lauderdale
$274Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
1:07 pm - 1:34 pmTLH  Tallahassee-SJU San Juan Luis Munoz Marin Intl
24h 27m1 stop Fort Lauderdale
Multiple Airlines Logo
7:00 am - 10:30 amSJU  San Juan Luis Munoz Marin Intl-TLH Tallahassee
27h 30m1 stop Fort Lauderdale
$301Multiple Airlines
Tue, Oct 20 - Mon, Oct 26
Multiple Airlines Logo
3:52 pm - 11:38 pmTLH  Tallahassee-SJU San Juan Luis Munoz Marin Intl
7h 46m1 stop Fort Lauderdale
Multiple Airlines Logo
1:59 am - 3:12 pmSJU  San Juan Luis Munoz Marin Intl-TLH Tallahassee
13h 13m2 stops Philadelphia Raleigh-Durham
$301Multiple Airlines
Thu, Oct 22 - Mon, Oct 26
American Airlines Logo
7:33 pm - 2:55 pmTLH  Tallahassee-STT Saint Thomas Island Cyril E King
19h 22m2 stops Charlotte Douglas Miami
American Airlines Logo
3:46 pm - 12:56 pmSTT  Saint Thomas Island Cyril E King-TLH Tallahassee
21h 10m2 stops Miami Dallas/Fort Worth
$418American Airlines
Sat, Nov 7 - Sat, Nov 14
American Airlines Logo
4:32 pm - 12:17 pmTLH  Tallahassee-STT Saint Thomas Island Cyril E King
18h 45m2 stops Charlotte Douglas Miami
American Airlines Logo
2:40 pm - 9:11 amSTT  Saint Thomas Island Cyril E King-TLH Tallahassee
19h 31m2 stops Miami Charlotte Douglas
$453American Airlines
Sat, Nov 7 - Sat, Nov 14
American Airlines Logo
6:44 pm - 12:17 pmTLH  Tallahassee-STT Saint Thomas Island Cyril E King
16h 33m2 stops Charlotte Douglas Miami
American Airlines Logo
2:40 pm - 7:53 pmSTT  Saint Thomas Island Cyril E King-TLH Tallahassee
6h 13m1 stop Miami
$453American Airlines
Tue, Oct 20 - Tue, Oct 27
Delta Logo
8:15 am - 4:49 pmTLH  Tallahassee-SJU San Juan Luis Munoz Marin Intl
8h 34m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:15 am - 2:39 pmSJU  San Juan Luis Munoz Marin Intl-TLH Tallahassee
7h 24m1 stop Atlanta Hartsfield-Jackson
$546Delta
Sun, Jan 3 - Fri, Jan 8
Delta Logo
5:35 am - 3:00 pmTLH  Tallahassee-NAS Nassau Intl
9h 25m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:55 pm - 8:46 pmNAS  Nassau Intl-TLH Tallahassee
5h 51m1 stop Atlanta Hartsfield-Jackson
$558Delta
Wed, Jan 13 - Tue, Jan 19
Delta Logo
5:35 am - 11:50 amTLH  Tallahassee-NAS Nassau Intl
6h 15m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:55 pm - 8:46 pmNAS  Nassau Intl-TLH Tallahassee
5h 51m1 stop Atlanta Hartsfield-Jackson
$562Delta
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?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $455, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Tallahassee to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

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 December and October, when the average cost of round-trip tickets is $954 and $859 respectively.

Good to know

Low season

October

Cheapest flight

$107
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Tallahassee to San Juan

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

 
See real verified KAYAK customer reviews for airlines flying from Tallahassee to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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.
7.1
American AirlinesOverall score based on 11898 reviews
7.9Crew
6.8Entertainment
7.5Boarding
7.2Comfort
6.4Food
Airline reviews

My flight was delayed several hours, which is to be expected (American never fails to disappoint me!), but the parts that really bothered me are as follows: 1) I was unable to add myself to the standby list for another flight in the app, nor could the gate agents figure out how to help me do so (the app is difficult to work with and simply did not allow me to perform the action of adding myself to the list) 2) When I asked the gate agents to add me to the standby list, the agent said that he had added me, but I was not able to confirm that I was on the list in the app; as it turns out, I had NOT been added to the list after all. He had lied to me and/or failed to add me to the list. 3) I figured out I had not been added to the standby list when I spoke to the (rather rude, snippy, and dismissive) other gate agent, who finally did add me to the list after giving me some pretty unnecessary attitude. I understand that gate agents experience the worst of stressed travelers every day, so I appreciate that I was eventually able to make it onto the standby flight with their help. However, the app needs some SERIOUS attention!

2.0 MediocreAnna, Aug 2026
Read more American Airlines reviews

My flight was delayed several hours, which is to be expected (American never fails to disappoint me!), but the parts that really bothered me are as follows: 1) I was unable to add myself to the standby list for another flight in the app, nor could the gate agents figure out how to help me do so (the app is difficult to work with and simply did not allow me to perform the action of adding myself to the list) 2) When I asked the gate agents to add me to the standby list, the agent said that he had added me, but I was not able to confirm that I was on the list in the app; as it turns out, I had NOT been added to the list after all. He had lied to me and/or failed to add me to the list. 3) I figured out I had not been added to the standby list when I spoke to the (rather rude, snippy, and dismissive) other gate agent, who finally did add me to the list after giving me some pretty unnecessary attitude. I understand that gate agents experience the worst of stressed travelers every day, so I appreciate that I was eventually able to make it onto the standby flight with their help. However, the app needs some SERIOUS attention!

Nice ! I am gold member at United Airlnes probably I will shift at American Airlines and JAL ! Thank you ! Kindly maintain quality service I fly often! ❤️

The flight was delayed 4 hours, and when we finally boarded, they told us that the fuel was only just then checked. So, we waited even longer to take off.

Everything was done like clockwork and I find no fault with the airline.

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

Quick flight. No time to stress over it. Over before it begins.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Not great. I understand delays happen due to weather and crew issues, but it was unacceptable that no agents were available at the counters inside the airport for customer service or help getting on a standby list. The app was not helpful either. I stood in line for an hour waiting for someone to show up at the gate to help me get on a standby flight. Customer care does not seem to be a priority.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports