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$289+ Cheap flights from Chattanooga (CHA) to Caribbean

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHA — SJU
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Cheap flight deals from Chattanooga to Caribbean

Keep the following information in mind while searching for Chattanooga to Caribbean flight deals. Data was last updated November 20, 2025.

Round-trip from

$288
(Kiwi.com)

Popular in

April

Cheapest in

October

Average price

$549
From Chattanooga Lovell Field to Caribbean
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Find flight deals from Chattanooga to Caribbean

Cheapest flights from Chattanooga to Caribbean
Explore the most affordable flight options available from Chattanooga to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2025.

This American Airlines deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/148:08 pmCHA - SJU
2 stops13h 01mAmerican Airlines
Mon 12/228:25 amSJU - CHA
1 stop7h 42mAmerican Airlines
Deal found 11/18$425
This American Airlines deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/92:25 pmCHA - SJU
1 stop6h 44mAmerican Airlines
Wed 12/108:20 amSJU - CHA
1 stop14h 31mAmerican Airlines
Deal found 11/18$440
This American Airlines deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:00 amCHA - SJU
1 stop11h 03mAmerican Airlines
Thu 12/118:18 amSJU - CHA
1 stop7h 54mAmerican Airlines
Deal found 11/18$445
This United Airlines deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/167:00 amCHA - SJU
1 stop7h 40mUnited Airlines
Tue 12/238:10 amSJU - CHA
1 stop9h 58mUnited Airlines
Deal found 11/18$478
This Mytrip deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:42 amCHA - SJU
3 stops39h 03mMultiple Airlines
Sat 12/135:00 pmSJU - CHA
3 stops29h 31mMultiple Airlines
Deal found 11/20$482
This American Airlines deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:05 amCHA - SJU
1 stop13h 04mAmerican Airlines
Mon 12/221:30 amSJU - CHA
1 stop17h 13mAmerican Airlines
Deal found 11/18$484
This American Airlines deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/512:07 pmCHA - SJU
1 stop8h 18mAmerican Airlines
Tue 12/93:10 pmSJU - CHA
1 stop9h 05mAmerican Airlines
Deal found 11/18$485
This American Airlines deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:00 amCHA - SJU
2 stops10h 08mAmerican Airlines
Sat 12/132:05 pmSJU - CHA
1 stop6h 35mAmerican Airlines
Deal found 11/20$510
This Mytrip deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/143:36 pmCHA - SJU
3 stops32h 09mMultiple Airlines
Mon 12/226:28 pmSJU - CHA
3 stops27h 59mMultiple Airlines
Deal found 11/18$544
This American Airlines deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:00 amCHA - SJU
2 stops9h 06mAmerican Airlines
Mon 12/82:36 pmSJU - CHA
2 stops10h 33mAmerican Airlines
Deal found 11/19$545
This Delta deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:45 amCHA - PLS
1 stop7h 00mDelta
Fri 12/122:10 pmPLS - CHA
1 stop7h 26mDelta
Deal found 11/18$564
This American Airlines deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:00 amCHA - MBJ
1 stop5h 21mAmerican Airlines
Tue 12/3011:49 amMBJ - CHA
1 stop5h 48mAmerican Airlines
Deal found 11/19$566

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chattanooga to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 20, 2025.
Use the filters below to find and compare flights from Chattanooga to Caribbean that are best for you.

Fly from

Chattanooga

Fly to

Caribbean

Route

Depart

Return

Price

ChattanoogaSan Juan

CHA - SJU

CHASJU

Chattanooga Lovell Field

Sun 1/18

9:28 pm-2:00 pm

1 stop15h 32m

San Juan Luis Munoz Marin Intl

Mon 1/26

11:15 am-9:06 pm

1 stop10h 51m

$289

ChattanoogaSan Juan

CHA - SJU

CHASJU

Chattanooga Lovell Field

Sat 2/7

7:20 pm-1:08 pm

1 stop16h 48m

San Juan Luis Munoz Marin Intl

Wed 2/11

7:07 am-6:04 pm

1 stop11h 57m

$365

ChattanoogaSan Juan

CHA - SJU

CHASJU

Chattanooga Lovell Field

Sun 2/8

6:00 am-3:00 pm

1 stop8h 00m

San Juan Luis Munoz Marin Intl

Fri 2/13

7:30 am-5:55 pm

1 stop11h 25m

$365

ChattanoogaSan Juan

CHA - SJU

CHASJU

Chattanooga Lovell Field

Sun 12/14

8:08 pm-10:09 am

2 stops13h 01m

San Juan Luis Munoz Marin Intl

Mon 12/22

8:25 am-3:07 pm

1 stop7h 42m

$425

ChattanoogaSan Juan

CHA - SJU

CHASJU

Chattanooga Lovell Field

Sun 1/25

2:00 pm-11:45 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Thu 1/29

7:30 am-1:05 pm

1 stop6h 35m

$433

ChattanoogaSan Juan

CHA - SJU

CHASJU

Chattanooga Lovell Field

Tue 12/9

7:16 pm-10:09 am

2 stops13h 53m

San Juan Luis Munoz Marin Intl

Wed 12/10

3:10 pm-9:51 pm

1 stop7h 41m

$440

ChattanoogaSan Juan

CHA - SJU

CHASJU

Chattanooga Lovell Field

Mon 2/9

6:00 am-6:22 pm

2 stops11h 22m

San Juan Luis Munoz Marin Intl

Sat 2/14

4:37 pm-11:59 pm

1 stop8h 22m

$450

ChattanoogaChristiansted

CHA - STX

CHASTX

Chattanooga Lovell Field

Mon 3/23

8:52 am-2:35 pm

1 stop5h 43m

Christiansted Henry Rohlsen

Mon 3/30

3:25 pm-8:41 am

1 stop17h 16m

$461

ChattanoogaNassau

CHA - NAS

CHANAS

Chattanooga Lovell Field

Tue 3/10

7:15 am-1:30 pm

1 stop6h 15m

Nassau Intl

Wed 3/11

3:40 pm-10:19 pm

1 stop6h 39m

$475

ChattanoogaSaint Thomas Island

CHA - STT

CHASTT

Chattanooga Lovell Field

Sat 1/24

7:20 pm-2:02 pm

2 stops17h 42m

Saint Thomas Island Cyril E King

Fri 1/30

4:47 pm-10:03 am

2 stops18h 16m

$479

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 30 results
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Best time to book a flight from Chattanooga to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Chattanooga with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chattanooga to Caribbean

What is the cheapest month to book a flight from Chattanooga to Caribbean?

Currently, August is the cheapest month in which you can book a flight from Chattanooga to Caribbean (average of $86). Flying from Chattanooga to Caribbean in May is currently the most expensive (average of $385). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHA to CB?

Find hourly flight availability from Chattanooga to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 20, 2025.

When flying from Chattanooga to Caribbean, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 16% versus a flight in the morning.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated November 20, 2025.
Peruse reviews from past customers who have flown with Delta and American Airlines from Chattanooga to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,002 reviews

Overall

7.9

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,002 reviews
Delta
7.9
Good
8,002 reviews

Overall

7.9

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,047 reviews
Delta
7.9
Good
8,002 reviews

Overall

7.9

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Chattanooga to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Chattanooga to Caribbean?

    For a flight from Chattanooga to Caribbean, you will be flying from Lovell Field. Chattanooga Lovell Field (CHA) is just 6.0 mi from the center of the city.

  • How long is the flight from Chattanooga to Caribbean?

    For as low as $475, American Airlines can have you in Caribbean from Chattanooga in 5h 05m. There are 830 mi between Chattanooga and Caribbean. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Chattanooga to Caribbean?

    Most travelers choose Chattanooga Lovell Field - Montego Bay Sangster Intl, Chattanooga Lovell Field - San Juan Luis Munoz Marin Intl or Chattanooga Lovell Field - Punta Cana when deciding on the best route from Chattanooga to Caribbean.

  • Can I find deals for flights from Chattanooga to Caribbean that include hotel bookings?

    Yes. In addition to deals on Chattanooga to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chattanooga to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chattanooga to Caribbean.

  • Can I find deals for business class flights from Chattanooga to Caribbean?

    Yes. Cheapflights offers flight deals from Chattanooga to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chattanooga to Caribbean?

    Currently, August is the cheapest month in which you can book a flight from Chattanooga to Caribbean (average of $86). Flying from Chattanooga to Caribbean in May is currently the most expensive (average of $385). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Chattanooga to Caribbean

Discover the top 2 airlines that operate flights from Chattanooga to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$322Average$640FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$401Average$654FlexibilityNo cancel feeOn-time71%

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