$169 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 4/6. 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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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$507
Montego Bay
Montego Bay1 stop$552
Oranjestad
Oranjestad1 stop$623
Nassau
Nassau1 stop$437
Providenciales
Providenciales1 stop$749
Port of Spain
Port of Spain1 stop$690
Bridgetown
Bridgetown1 stop$602
Puerto Plata
Puerto Plata2 stops$3,445
Punta Cana
Punta Cana2 stops$507
Montego Bay
Montego Bay1 stop$552
Oranjestad
Oranjestad1 stop$623
Nassau
Nassau1 stop$437
Providenciales
Providenciales1 stop$749
Port of Spain
Port of Spain1 stop$690
Bridgetown
Bridgetown1 stop$602
Puerto Plata
Puerto Plata2 stops$3,445

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, Mar 22 - Wed, Mar 25
Multiple Airlines Logo
9:36 pm - 2:26 pm
CHA
-
SJU
16h 50m
1 stop
Multiple Airlines Logo
1:45 am - 8:46 pm
SJU
-
CHA
19h 01m
2 stops
$326Multiple Airlines
Sun, Mar 22 - Sat, Mar 28
Multiple Airlines Logo
9:36 pm - 2:26 pm
CHA
-
SJU
16h 50m
1 stop
Multiple Airlines Logo
1:45 am - 8:46 pm
SJU
-
CHA
19h 01m
2 stops
$332Multiple Airlines
Thu, Feb 12 - Wed, Feb 25
Multiple Airlines Logo
3:33 pm - 11:09 pm
CHA
-
SJU
30h 36m
2 stops
Multiple Airlines Logo
4:31 pm - 8:33 pm
SJU
-
CHA
29h 02m
1 stop
$339Multiple Airlines
Sat, Mar 21 - Wed, Mar 25
American Airlines Logo
8:01 pm - 10:40 am
CHA
-
SJU
14h 39m
1 stop
American Airlines Logo
1:44 pm - 10:51 pm
SJU
-
CHA
9h 07m
1 stop
$426American Airlines
Mon, Mar 16 - Wed, Mar 18
American Airlines Logo
8:06 pm - 11:55 am
CHA
-
SJU
15h 49m
1 stop
American Airlines Logo
1:30 am - 11:46 am
SJU
-
CHA
10h 16m
1 stop
$436American Airlines
Thu, May 14 - Tue, May 19
United Airlines Logo
4:42 pm - 11:50 pm
CHA
-
SJU
7h 08m
1 stop
United Airlines Logo
3:56 pm - 12:15 am
SJU
-
CHA
8h 19m
1 stop
$456United Airlines
Mon, Mar 9 - Mon, Mar 16
United Airlines Logo
6:30 am - 2:19 pm
CHA
-
PUJ
7h 49m
1 stop
United Airlines Logo
3:25 pm - 10:12 am
PUJ
-
CHA
18h 47m
1 stop
$522United Airlines
Sun, Feb 22 - Thu, Feb 26
Delta Logo
5:40 am - 3:38 pm
CHA
-
GND
8h 58m
1 stop
Delta Logo
4:53 pm - 8:58 am
GND
-
CHA
17h 05m
1 stop
$687Delta
Fri, Feb 20 - Thu, Feb 26
Delta Logo
5:40 am - 3:38 pm
CHA
-
GND
8h 58m
1 stop
Delta Logo
4:53 pm - 8:58 am
GND
-
CHA
17h 05m
1 stop
$712Delta
Mon, Feb 2 - Fri, Feb 6
WestJet Logo
2:58 pm - 7:17 pm
CHA
-
MBJ
28h 19m
2 stops
WestJet Logo
2:55 pm - 6:30 pm
MBJ
-
CHA
27h 35m
2 stops
$3,433WestJet
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 $745 and $668 respectively.

Good to know

Low seasonAugust
Cheapest flight$169
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 2% 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.

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 8110 reviews
8.1Boarding
8.5Crew
7.2Food
7.9Comfort
7.8Entertainment
Airline reviews

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

2.0 MediocreGary, Jan 2026
CLE - DTW
Read more Delta reviews

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

2 hour delay due to equipment failure. No updates via the app and airport screens (which continued to show a departure time in the past). AA eventually switched planes and the new plane was not catered or cleaned correctly.

I booked an aisle seat and was given a middle. At 6'4" 230lbs, it is not ideal to fly in the middle row for myself and passengers.

Trip delayed for 2 hours because of rain. We boarded and have to get down the flight and reboard again.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

This flight captain and crew were amazing, started ahead of time of departure and reached 30 mins before arrival time. Amazing!

Long delays, lack of information about the status of the flight. The flight was delayed 4 times.

Could we please end the loud announcements about credit card offers on your flights? We are trying to sleep, work, watch videos, etc. and if we need a credit card, we will ask for one. Flying is already not what it used to be.

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

Enough space,crew was helpful,food was good.The gates are way far especially for travelers with health issues

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports