$217 Find Cheap Flights from Chattanooga to Caribbean Islands - 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 Islands departing on 7/5. 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 Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chattanooga to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chattanooga to Caribbean Islands, as well as popular online travel agencies
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.

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

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

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chattanooga to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$596
Montego Bay
Montego Bay1 stop$447
Oranjestad
Oranjestad1 stop$525
Nassau
Nassau1 stop$577
Providenciales
Providenciales1 stop$635
Port of Spain
Port of Spain1 stop$642
Puerto Plata
Puerto Plata2 stops$655
Punta Cana
Punta Cana1 stop$596
Montego Bay
Montego Bay1 stop$447
Oranjestad
Oranjestad1 stop$525
Nassau
Nassau1 stop$577
Providenciales
Providenciales1 stop$635
Port of Spain
Port of Spain1 stop$642
Puerto Plata
Puerto Plata2 stops$655

Book Cheap Chattanooga to Caribbean Islands 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 Islands 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 Islands

Sun, Oct 11 - Wed, Oct 21
Multiple Airlines Logo
9:34 am - 11:38 pm
CHA
-
SJU
14h 04m
1 stop
Multiple Airlines Logo
5:12 pm - 8:09 am
SJU
-
CHA
14h 57m
1 stop
$338Multiple Airlines
Sun, Oct 11 - Wed, Oct 21
Multiple Airlines Logo
9:34 am - 11:38 pm
CHA
-
SJU
14h 04m
1 stop
Multiple Airlines Logo
5:12 pm - 8:09 am
SJU
-
CHA
14h 57m
1 stop
$345Multiple Airlines
Thu, Oct 15 - Wed, Oct 21
Multiple Airlines Logo
9:04 am - 11:57 pm
CHA
-
SJU
14h 53m
2 stops
Multiple Airlines Logo
5:12 pm - 8:09 am
SJU
-
CHA
14h 57m
1 stop
$355Multiple Airlines
Thu, Oct 15 - Wed, Oct 21
Multiple Airlines Logo
9:04 am - 11:38 pm
CHA
-
SJU
14h 34m
1 stop
Multiple Airlines Logo
5:12 pm - 8:09 am
SJU
-
CHA
14h 57m
1 stop
$372Multiple Airlines
Wed, Dec 2 - Wed, Dec 9
American Airlines Logo
8:08 pm - 3:25 pm
CHA
-
STT
18h 17m
2 stops
American Airlines Logo
4:16 pm - 8:38 am
STT
-
CHA
17h 22m
2 stops
$403American Airlines
Wed, Dec 2 - Wed, Dec 9
American Airlines Logo
8:08 pm - 3:25 pm
CHA
-
STT
18h 17m
2 stops
American Airlines Logo
6:17 pm - 8:38 am
STT
-
CHA
15h 21m
2 stops
$419American Airlines
Wed, Sep 16 - Sat, Sep 26
Delta Logo
2:32 pm - 10:19 pm
CHA
-
SJU
7h 47m
1 stop
Delta Logo
7:00 am - 1:47 pm
SJU
-
CHA
6h 47m
1 stop
$436Delta
Thu, Jul 23 - Wed, Jul 29
United Airlines Logo
6:00 am - 3:35 pm
CHA
-
AUA
9h 35m
1 stop
United Airlines Logo
3:10 pm - 11:06 pm
AUA
-
CHA
7h 56m
1 stop
$525United Airlines
Tue, Oct 20 - Wed, Oct 21
Delta Logo
5:30 am - 1:39 pm
CHA
-
STT
8h 09m
1 stop
Delta Logo
2:49 pm - 11:51 pm
STT
-
CHA
9h 02m
1 stop
$536Delta
Thu, Jul 30 - Mon, Aug 3
United Airlines Logo
7:00 am - 1:47 pm
CHA
-
NAS
6h 47m
1 stop
United Airlines Logo
4:58 pm - 11:06 pm
NAS
-
CHA
6h 08m
1 stop
$586United Airlines
Booking Insights

KAYAK's insights & trends for Chattanooga to Caribbean Islands flights

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

Can I save money by flying with a layover from Chattanooga to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $349, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chattanooga to Caribbean Islands, 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 Islands is June, when tickets cost $263 (return) on average. On the other hand, the most expensive months are November and March, when the average cost of round-trip tickets is $561 and $557 respectively.

Good to know

Low seasonApril
Cheapest flight$217
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 26% increase in price.
Flight from Chattanooga to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

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

    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 Islands 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 Islands?

    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 Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from Chattanooga to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chattanooga to Caribbean Islands? 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.
7.8
DeltaOverall score based on 8455 reviews
8.1Boarding
8.5Crew
7.2Food
7.8Comfort
7.8Entertainment
Airline reviews

I was in Comfort and we didn’t get any drinks, chips or anything! First Class got full service on the flight and Comfort got nothing. Seat was horrible and uncomfortable

4.0 OkayLinda, Jun 2026
BNA - ATL
Read more Delta reviews

I was in Comfort and we didn’t get any drinks, chips or anything! First Class got full service on the flight and Comfort got nothing. Seat was horrible and uncomfortable

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

The tray table was broken and the food was terrible.

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

Good flights. On time. They had a gluten free snack option which was nice

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

The seats are uncomfortable and there was no power to recharge a phone.

Air condition was not working for long both after boarding and also after landing ; unbearably hot and suffocating

It was canceled at the last minute. While I was literally at the airport. Messed my entire trip up.

Flight was on-time, boarding was flawless and the crew was friendly.

Horrible experience upon landing. Probably more due to DCA utter incompetence than AA.

Not to have gotten delayed by 2+ hours for the fourth straight American flight. They're the worst.

American has been able to implement an algorithm that makes it possible for nearly every one of my evening flights to be late. Congratulations!

This was a horrible experience. I’ve experienced several delays at this point and still not home. I was supposed to be home by 8:30 last night and here I sit at 7 am on a plane STILL unable to go home because of American Airlines.

It was good. But the gate team made me check my carry on when there was plenty of space for my luggage on the plane. Otherwise our trip was fine.

The flight was good. We had to spend almost an hour on the tarmac when we arrived in Dallas. Waiting for a gate. What’s the point of arriving early if you have no gate to park at?

Pulled out of the gate only to sit in the tarmac for an hour and a half for paperwork. Paperwork. Went back to the gate to refuel.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports