$153 Find Cheap Flights from Chattanooga to Caribbean

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 3/19. 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

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Cheap Flights from Chattanooga to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$386
Montego Bay
Montego Bay2 stops$347
Oranjestad
Oranjestad1 stop$567
Nassau
Nassau1 stop$433
Providenciales
Providenciales1 stop$610
Port of Spain
Port of Spain1 stop$679
Puerto Plata
Puerto Plata2 stops$553
Punta Cana
Punta Cana1 stop$386
Montego Bay
Montego Bay2 stops$347
Oranjestad
Oranjestad1 stop$567
Nassau
Nassau1 stop$433
Providenciales
Providenciales1 stop$610
Port of Spain
Port of Spain1 stop$679
Puerto Plata
Puerto Plata2 stops$553

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

Sun, May 10 - Tue, May 19
Multiple Airlines Logo
4:11 pm - 12:33 pm
CHA
-
SJU
20h 22m
1 stop
Multiple Airlines Logo
1:59 am - 8:07 am
SJU
-
CHA
30h 08m
2 stops
$255Multiple Airlines
Sun, May 10 - Sat, May 16
Multiple Airlines Logo
4:11 pm - 12:33 pm
CHA
-
SJU
20h 22m
1 stop
Multiple Airlines Logo
3:36 pm - 9:12 pm
SJU
-
CHA
29h 36m
1 stop
$258Multiple Airlines
Sun, May 10 - Wed, May 20
Multiple Airlines Logo
4:11 pm - 12:33 pm
CHA
-
SJU
20h 22m
1 stop
Multiple Airlines Logo
3:36 pm - 8:07 am
SJU
-
CHA
16h 31m
1 stop
$269Multiple Airlines
Thu, May 7 - Thu, May 14
Multiple Airlines Logo
4:11 pm - 8:49 pm
CHA
-
SJU
28h 38m
1 stop
Multiple Airlines Logo
6:00 am - 9:12 pm
SJU
-
CHA
15h 12m
1 stop
$273Multiple Airlines
Mon, May 4 - Fri, May 8
American Airlines Logo
8:04 pm - 11:51 am
CHA
-
MBJ
16h 47m
2 stops
American Airlines Logo
12:56 pm - 8:38 am
MBJ
-
CHA
18h 42m
2 stops
$347American Airlines
Mon, May 4 - Fri, May 8
American Airlines Logo
8:04 pm - 1:19 pm
CHA
-
MBJ
18h 15m
1 stop
American Airlines Logo
4:37 pm - 10:40 am
MBJ
-
CHA
17h 03m
2 stops
$353American Airlines
Wed, May 13 - Tue, May 19
United Airlines Logo
7:15 am - 1:47 pm
CHA
-
NAS
6h 32m
1 stop
United Airlines Logo
2:53 pm - 11:03 pm
NAS
-
CHA
8h 10m
1 stop
$506United Airlines
Sun, Apr 26 - Thu, Apr 30
Delta Logo
7:00 am - 4:33 pm
CHA
-
NAS
9h 33m
1 stop
Delta Logo
5:58 pm - 11:53 pm
NAS
-
CHA
5h 55m
1 stop
$526Delta
Thu, Apr 9 - Thu, Apr 16
United Airlines Logo
6:30 am - 3:20 pm
CHA
-
AUA
8h 50m
1 stop
United Airlines Logo
1:50 pm - 11:59 pm
AUA
-
CHA
10h 09m
1 stop
$567United Airlines
Wed, Mar 11 - Thu, Mar 19
Delta Logo
6:15 pm - 12:00 pm
CHA
-
PLS
17h 45m
2 stops
Delta Logo
1:25 pm - 8:59 am
PLS
-
CHA
19h 34m
2 stops
$620Delta
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 October, when tickets cost $450 (return) on average. On the other hand, the most expensive months are April and February, when the average cost of round-trip tickets is $758 and $705 respectively.

Good to know

Low seasonAugust
Cheapest flight$153
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chattanooga to Christiansted

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 8212 reviews
8.5Crew
7.9Comfort
8.1Boarding
7.8Entertainment
7.2Food
Airline reviews

Terrible. Four hour delay because Delta could not find crew to man the aircraft. Terrible communication. Terrible insight into the delays. One of the worst flight experiences I’ve had.

2.0 MediocreDonna, Feb 2026
DEN - LGA
Read more Delta reviews

Terrible. Four hour delay because Delta could not find crew to man the aircraft. Terrible communication. Terrible insight into the delays. One of the worst flight experiences I’ve had.

It was good. The leg room was not great in Row 1.

The landing was the worst I’ve experienced with a flight.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

First flight out and was 85 minutes delayed. Notification came out way too late

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Everything was good. Flight was very full so crew was busy. After we boarded and plane pulled away from the gate, we were delayed about 40 minutes- sitting on the runway - due to weather en route or at the destination. While weather is not the fault of the airline- it’s terrible to sit on a plane and not moving.

We missed our flight and got stranded in Miami where we had to rent a hotel we could not afford. they would not work with us because they said it was weather related even though the gate attendant said it was not. I could go on but trying to get satisfaction has wore me down, which I believe is the intent. My only solution is to never fly AA again.

No Snacks or Entertainment. The flight was short, snacks should still be given.

We lost a day of our vacation because AA did not get the plane to the gate on time. Even though the gate attendant was very clear that it was not weather related, AA would do nothing because there was some snow that day. They basically said the gate attendant was wrong even though she was on the front line of the situation and they were not.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

The flight was fine. It's the satellite terminal that supports American eagle flights is what sucks. There is only one food option and everything there is way overpriced. I mean I know it's airport pricing, but it's even crazier than that. I bought a sandwich in a plastic container for $18.

Overall it was a good flight. Because we traveled on a Saturday we were upgraded to FC since my wife and I are both Executive Platinum. The only areas for improvement we noted are better snack assortment and perhaps a little nicer plane as American is flying some older planes now. Everything else on this flight was excellent, which is frankly not the norm for American since we have had multiple issues on prior AA flights.

The smell from the bathroom kept wafting through the cabin. It made people sick.

The flight was really crowded. Flight attendants were just ok.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports