$229 Find Cheap Flights from Chattanooga to Caribbean - 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 Chattanooga to Caribbean departing on 8/1. 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 Caribbean

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

Save 21% or moreCompare multiple travel sites with one search.

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

Free to useThere are no hidden charges or fees.

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

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chattanooga to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$538
Montego Bay
Montego Bay1 stop$437
Oranjestad
Oranjestad1 stop$570
Nassau
Nassau1 stop$536
Providenciales
Providenciales1 stop$730
Port of Spain
Port of Spain1 stop$770
Bridgetown
Bridgetown1 stop$816
Puerto Plata
Puerto Plata2 stops$655
Punta Cana
Punta Cana2 stops$538
Montego Bay
Montego Bay1 stop$437
Oranjestad
Oranjestad1 stop$570
Nassau
Nassau1 stop$536
Providenciales
Providenciales1 stop$730
Port of Spain
Port of Spain1 stop$770
Bridgetown
Bridgetown1 stop$816
Puerto Plata
Puerto Plata2 stops$655

Book Cheap Chattanooga to Caribbean Plane Tickets

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

Thu, Jul 23 - Wed, Jul 29
Multiple Airlines Logo
8:59 am - 12:07 am
CHA
-
SJU
15h 08m
2 stops
Multiple Airlines Logo
6:00 am - 8:09 am
SJU
-
CHA
26h 09m
1 stop
$345Multiple Airlines
Sun, Jul 19 - Wed, Jul 29
Multiple Airlines Logo
8:59 am - 12:07 am
CHA
-
SJU
15h 08m
2 stops
Multiple Airlines Logo
6:00 am - 8:09 am
SJU
-
CHA
26h 09m
1 stop
$353Multiple Airlines
Sun, Jul 19 - Wed, Jul 29
Multiple Airlines Logo
8:59 am - 4:05 pm
CHA
-
SJU
7h 06m
1 stop
Multiple Airlines Logo
6:00 am - 8:09 am
SJU
-
CHA
26h 09m
1 stop
$360Multiple Airlines
Thu, Jul 23 - Sat, Aug 1
Multiple Airlines Logo
8:59 am - 12:07 am
CHA
-
SJU
15h 08m
2 stops
Multiple Airlines Logo
6:00 am - 8:19 am
SJU
-
CHA
26h 19m
1 stop
$374Multiple Airlines
Wed, Aug 26 - Tue, Sep 1
American Airlines Logo
4:08 pm - 12:53 pm
CHA
-
STT
20h 45m
2 stops
American Airlines Logo
1:49 pm - 11:40 am
STT
-
CHA
21h 51m
2 stops
$403American Airlines
Tue, Aug 18 - Tue, Aug 25
Delta Logo
5:35 am - 1:42 pm
CHA
-
SJU
8h 07m
1 stop
Delta Logo
5:49 pm - 11:43 pm
SJU
-
CHA
5h 54m
1 stop
$416Delta
Wed, Dec 2 - Wed, Dec 9
American Airlines Logo
8:08 pm - 3:25 pm
CHA
-
STT
18h 17m
2 stops
American Airlines Logo
2:49 pm - 8:38 am
STT
-
CHA
18h 49m
2 stops
$419American Airlines
Mon, Jul 20 - Tue, Jul 28
Delta Logo
2:50 pm - 8:45 pm
CHA
-
SJU
5h 55m
1 stop
Delta Logo
6:00 am - 2:02 pm
SJU
-
CHA
8h 02m
1 stop
$426Delta
Thu, Sep 17 - Mon, Sep 21
United Airlines Logo
6:10 pm - 11:43 am
CHA
-
MBJ
18h 33m
1 stop
United Airlines Logo
12:52 pm - 5:05 pm
MBJ
-
CHA
27h 13m
1 stop
$448United Airlines
Wed, Jul 8 - Tue, Jul 14
United Airlines Logo
7:00 am - 3:56 pm
CHA
-
NAS
8h 56m
1 stop
United Airlines Logo
4:58 pm - 11:06 pm
NAS
-
CHA
6h 08m
1 stop
$601United Airlines
Booking Insights

KAYAK's insights & trends for Chattanooga to Caribbean flights

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

What is the cheapest month to fly from Chattanooga to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chattanooga to Caribbean, 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 Chattanooga to Caribbean is June, when tickets cost $263 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $557 and $487 respectively.

Good to know

Low seasonApril
Cheapest flight$229
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Chattanooga to Saint Thomas Island

FAQs - booking Caribbean flights

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

    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 Chattanooga to Caribbean.

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

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

    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 Chattanooga to Caribbean 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 Chattanooga to Caribbean?

    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 Chattanooga to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chattanooga to Caribbean

 
Need help choosing which airline to fly with from Chattanooga to Caribbean? 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.
7.9
DeltaOverall score based on 8405 reviews
7.8Comfort
8.1Boarding
7.2Food
8.5Crew
7.8Entertainment
Airline reviews

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

4.0 OkayMarilyn, Jun 2026
DEN - ATL
Read more Delta reviews

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

Crew were professional and kind. The flight was smooth. But... The internet, which we paid 35 dollars for, did not work for most of the flight. This made providing media for our child an uncomfortable hassle.

Overall fine. Seemed like one of the older model planes? Crew was mostly very kind, though some of the female attendants were a rather abrupt during the food service.

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

Two hours delay, probably one hour because they didn’t bring catering and they had to bring water in board. There a change of aircraft. But delays galore at CLT so it must be a CLT and/or AA operation issue. The 1 hr additional delays because nobody could bring 2 packs of water sooner is probably the best example of this airline operates

Flight was delayed 5 hours. Initial reason for delay was 'maintenance' - which makes sense. Then, the additional 2 hours continued to say it was maintenance - when I know EWR had a 2 hour delay. AA did not say that. Additionally, when boarding, there was only one agent at the counter for a long time - until another came to help. After boarding, we had to wait another 45 minutes due to 'no catering'. So while we waited for catering, AA continued to board additional passengers - which seemed odd - and raised questions about what really was going on. I sat in First Class. During the flight, the flight crew allowed a significant number of non-First Class passengers to use the front bathroom - which created a very crowded environment in First Class which was uncomfortable. This also delayed First Class passengers from using the bathroom. Overall, horrible experience.

The Charleston, WV airport was cute. Very good staff and small enough to feel comfortable. The plane had more leg room than bigger planes. Much more comfortable.

Another uncoordinated American experience. Always surprises me at DFW for them of all places. Have to take this flight as there are no other good time options. We knew from the start that something was wrong, but the pilot wouldn't tell us. I just watched my Kayak app grow the delay by 10 minutes as it went to 3.5 hours. They were uncoordinated with maintenance (as maintenance, when finally arriving, knew within 15 minutes the plane wasn't going. No 'sorry' or 'this is what is going on' comment. The pilot seemed unfazed / didn't care about the process we were going through.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports