$268 Find Cheap Flights from Caribbean Islands to Tallahassee

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Tallahassee departing on 5/27. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Tallahassee

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean Islands to Tallahassee

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Tallahassee 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 Caribbean Islands to Tallahassee

Tue, Jun 30 - Sun, Jul 5
American Airlines Logo
7:16 pm - 9:02 am
SJU
-
TLH
13h 46m
1 stop
American Airlines Logo
8:20 pm - 11:04 am
TLH
-
SJU
14h 44m
1 stop
$436American Airlines
Wed, Jun 17 - Thu, Jun 25
American Airlines Logo
7:16 pm - 9:02 am
SJU
-
TLH
13h 46m
1 stop
American Airlines Logo
6:00 am - 9:58 pm
TLH
-
SJU
15h 58m
1 stop
$456American Airlines
Thu, May 28 - Tue, Jun 2
American Airlines Logo
6:00 am - 7:23 pm
SJU
-
TLH
13h 23m
2 stops
American Airlines Logo
6:00 am - 9:59 pm
TLH
-
SJU
15h 59m
1 stop
$476American Airlines
Fri, May 22 - Mon, May 25
American Airlines Logo
5:30 am - 7:34 pm
SJU
-
TLH
14h 04m
1 stop
American Airlines Logo
7:48 pm - 9:39 am
TLH
-
SJU
13h 51m
2 stops
$516American Airlines
Tue, Jun 30 - Sun, Jul 5
American Airlines Logo
6:01 am - 7:23 pm
SJU
-
TLH
13h 22m
2 stops
American Airlines Logo
8:20 pm - 11:04 am
TLH
-
SJU
14h 44m
1 stop
$526American Airlines
Wed, May 27 - Thu, May 28
American Airlines Logo
6:00 am - 7:23 pm
SJU
-
TLH
13h 23m
2 stops
American Airlines Logo
7:48 pm - 9:39 am
TLH
-
SJU
13h 51m
2 stops
$546American Airlines
Thu, Jun 25 - Fri, Sep 25
Delta Logo
6:02 pm - 10:53 pm
NAS
-
TLH
4h 51m
1 stop
Delta Logo
5:35 am - 1:49 pm
TLH
-
NAS
8h 14m
1 stop
$562Delta
Fri, May 22 - Mon, May 25
American Airlines Logo
11:55 am - 11:38 pm
SJU
-
TLH
11h 43m
2 stops
American Airlines Logo
7:48 pm - 9:39 am
TLH
-
SJU
13h 51m
2 stops
$566American Airlines
Thu, Jun 25 - Fri, Sep 25
American Airlines Logo
2:55 pm - 11:59 pm
NAS
-
TLH
9h 04m
1 stop
American Airlines Logo
6:27 am - 1:05 pm
TLH
-
NAS
6h 38m
1 stop
$571American Airlines
Wed, May 13 - Sun, May 17
Delta Logo
7:30 am - 4:31 pm
SJU
-
TLH
9h 01m
1 stop
Delta Logo
6:15 am - 12:01 pm
TLH
-
SJU
5h 46m
1 stop
$596Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$268
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from San Juan to Tallahassee

FAQs for booking flights from Caribbean Islands to Tallahassee

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

    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 Caribbean Islands to Tallahassee.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Tallahassee from 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 Caribbean Islands to Tallahassee?

    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 to Tallahassee with an airline and back to Caribbean Islands with another airline.

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

    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 to Tallahassee from 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 Caribbean Islands to Tallahassee

 
Need help choosing which airline to fly with from Caribbean Islands to Tallahassee? 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 11681 reviews
6.4Food
7.9Crew
6.9Entertainment
7.5Boarding
7.2Comfort
Airline reviews

Poor... food was horrible, boarding very slow, service on board mediocre

4.0 Okayedgar, Apr 2026
EZE - MIA
Read more American Airlines reviews

Poor... food was horrible, boarding very slow, service on board mediocre

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

Departed late but made up the time en route. Uncrowded and clean aircraft.

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

I have been flying American Airlines—almost exclusively—for years. The airline is consistent with fares, timely departures/arrivals, and customer service, whether on the phone or in the air.

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

I would have liked vegetarian and gluten free options for evening dinner time flight. I would have like a pillow on the international overnight flight . The veg wrap and oaten desert on the international flight was good

Traveling to a place near Tallahassee?

Book flights to Tallahassee if you plan to visit one of these locations
Thomasville
Midway

Everything you need to know for your flight to Tallahassee

Information on the airport you'll fly into in Tallahassee