$258 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 3/12. 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$499
Montego Bay
Montego Bay1 stop$561
Oranjestad
Oranjestad1 stop$535
Nassau
Nassau1 stop$500
Providenciales
Providenciales1 stop$529
Bridgetown
Bridgetown1 stop$706
Punta Cana
Punta Cana1 stop$499
Montego Bay
Montego Bay1 stop$561
Oranjestad
Oranjestad1 stop$535
Nassau
Nassau1 stop$500
Providenciales
Providenciales1 stop$529
Bridgetown
Bridgetown1 stop$706

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

Mon, Jan 19 - Sun, Jan 25
Multiple Airlines Logo
9:56 pm - 11:33 pm
CHA
-
SJU
24h 37m1 stop
Multiple Airlines Logo
2:59 am - 9:06 pm
SJU
-
CHA
19h 07m2 stops
$314Multiple Airlines
Mon, Jan 19 - Mon, Jan 26
Multiple Airlines Logo
9:56 pm - 9:47 am
CHA
-
SJU
10h 51m1 stop
Multiple Airlines Logo
11:15 am - 9:06 pm
SJU
-
CHA
10h 51m1 stop
$334Multiple Airlines
Sun, Feb 8 - Fri, Feb 13
American Airlines Logo
6:00 am - 1:08 pm
CHA
-
SJU
6h 08m1 stop
American Airlines Logo
12:31 pm - 11:58 pm
SJU
-
CHA
12h 27m1 stop
$385American Airlines
Wed, Feb 4 - Mon, Feb 9
American Airlines Logo
8:00 am - 8:50 pm
CHA
-
SJU
11h 50m1 stop
American Airlines Logo
5:55 pm - 10:02 am
SJU
-
CHA
17h 07m1 stop
$405American Airlines
Thu, Mar 5 - Sat, Mar 14
Multiple Airlines Logo
6:28 pm - 1:37 am
CHA
-
SJU
30h 09m2 stops
Multiple Airlines Logo
3:22 pm - 4:36 pm
SJU
-
CHA
25h 14m1 stop
$430Multiple Airlines
Wed, Feb 25 - Sat, Feb 28
Delta Logo
6:45 am - 5:02 pm
CHA
-
NAS
10h 17m1 stop
Delta Logo
1:15 pm - 5:14 pm
NAS
-
CHA
3h 59m1 stop
$500Delta
Wed, Feb 25 - Sat, Feb 28
Delta Logo
5:40 am - 3:13 pm
CHA
-
NAS
9h 33m2 stops
Delta Logo
1:15 pm - 5:14 pm
NAS
-
CHA
3h 59m1 stop
$504Delta
Mon, Apr 27 - Fri, May 1
United Airlines Logo
6:30 am - 12:50 pm
CHA
-
MBJ
7h 20m1 stop
United Airlines Logo
2:40 pm - 4:13 pm
MBJ
-
CHA
24h 33m1 stop
$664United Airlines
Mon, Feb 23 - Wed, Feb 25
United Airlines Logo
6:30 am - 4:18 pm
CHA
-
STT
8h 48m1 stop
United Airlines Logo
3:05 pm - 4:47 pm
STT
-
CHA
26h 42m1 stop
$730United Airlines
Wed, Feb 18 - Sat, Feb 21
WestJet Logo
2:44 pm - 1:49 pm
CHA
-
MBJ
23h 05m2 stops
WestJet Logo
2:50 pm - 5:47 pm
MBJ
-
CHA
26h 57m2 stops
$2,359WestJet
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 January, when the average cost of round-trip tickets is $745 and $680 respectively.

What’s the cheapest day of the week to fly from Chattanooga to Caribbean?

The average price of all round-trip flights from Chattanooga to Caribbean clicked on KAYAK for each day over the last 12 months.

For Chattanooga to Caribbean, Monday is the cheapest day to fly on average and Friday is the most expensive. Flying from Caribbean back to Chattanooga, the best deals are generally found on Wednesday, with Thursday being the most expensive.

Good to know

Low seasonAugust
Cheapest flight$258
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chattanooga to San Juan

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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the afternoon, when round-trip flights cost $580 on average. Morning departures are around 7% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally at night, which is peak travel time and where the average cost of a ticket is $859.

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 8014 reviews
8.1Boarding
7.9Comfort
7.9Entertainment
7.3Food
8.5Crew
Airline reviews

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

2.0 MediocrePeter, Dec 2025
JFK - MEM
Read more Delta reviews

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great. I had to modify a flight. That was easy and free. Thank You

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Not great. Booked Extra seats and got nothing extra at all. It’s basically a big budget airline.

The pilot greased the landing and the crew was fantastic.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

delayed due to weather. Could not communicate with family since the wifi was broken

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was delayed 17 hours due to aircraft issues. American did provide hotel, transportation and meals, 3 hours past boarding time, but it took us another hour to get the vouchers.

Flight was on time is the only good thing. Person loading the plane called 1-6 to board at the same time, made it chaotic. Plane was too small for even putting backpacks in overhead. Seat for normal sized people were too small. The WIFI didn't work. When we landed had to wait because not enough ground crew.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports