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$101+ Cheap flights from Louisville (SDF) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Feb 13 — Feb 201
Fri 2/13
Fri 2/20
1 adult, Economy
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Cheap flight deals from Louisville to Caribbean

Keep the following information in mind while searching for Louisville to Caribbean flight deals. Data was last updated January 14, 2026.

Round-trip from

$222
(Cheapflightsfares)

One-way from

$101
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$345
From Louisville Intl to Caribbean
Search Deals
One-way flight from Louisville Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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Find flight deals from Louisville to Caribbean

Cheapest flights from Louisville to Caribbean
Explore the most affordable flight options available from Louisville to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 14, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/161:19 pm
SDF
-
SJU
1 stop8h 50m
Spirit Airlines
Wed 2/256:00 am
SJU
-
SDF
1 stop7h 21m
Spirit Airlines
Deal found 1/12$222
This Cheapflightsfares deal was found by Cheapflights users on 1/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/231:19 pm
SDF
-
SJU
1 stop8h 50m
Spirit Airlines
Fri 2/276:00 am
SJU
-
SDF
1 stop7h 21m
Spirit Airlines
Deal found 1/12$223
This American Airlines deal was found by Cheapflights users on 1/12. 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 2/86:00 am
SDF
-
SJU
2 stops9h 30m
American Airlines
Thu 2/127:33 am
SJU
-
SDF
1 stop11h 04m
American Airlines
Deal found 1/12$226
This Delta deal was found by Cheapflights users on 1/13. 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 2/245:33 am
SDF
-
SJU
1 stop7h 59m
Delta
Wed 3/46:37 pm
SJU
-
SDF
1 stop6h 21m
Delta
Deal found 1/13$246
This Expedia deal was found by Cheapflights users on 1/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/301:55 pm
SDF
-
SJU
1 stop8h 38m
Spirit Airlines
Fri 2/66:00 am
SJU
-
SDF
1 stop8h 00m
Spirit Airlines
Deal found 1/13$259
This American Airlines deal was found by Cheapflights users on 1/12. 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.
Thu 1/297:00 am
SDF
-
SJU
1 stop15h 56m
American Airlines
Sat 2/76:05 am
SJU
-
SDF
1 stop18h 14m
American Airlines
Deal found 1/12$266
This United Airlines deal was found by Cheapflights users on 1/12. 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.
Mon 3/92:35 pm
SDF
-
SJU
1 stop6h 47m
United Airlines
Tue 3/101:05 am
SJU
-
SDF
2 stops12h 12m
United Airlines
Deal found 1/12$271
This Cheapflightsfares deal was found by Cheapflights users on 1/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/251:19 pm
SDF
-
SJU
1 stop8h 50m
Spirit Airlines
Mon 3/26:00 am
SJU
-
SDF
1 stop7h 21m
Spirit Airlines
Deal found 1/11$277
This American Airlines deal was found by Cheapflights users on 1/13. 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.
Thu 1/291:15 pm
SDF
-
SJU
2 stops9h 44m
American Airlines
Fri 2/68:20 am
SJU
-
SDF
2 stops11h 19m
American Airlines
Deal found 1/13$286
This United Airlines deal was found by Cheapflights users on 1/13. 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.
Fri 1/302:05 pm
SDF
-
SJU
2 stops9h 31m
United Airlines
Thu 2/52:05 am
SJU
-
SDF
2 stops12h 19m
United Airlines
Deal found 1/13$294
This American Airlines deal was found by Cheapflights users on 1/12. 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 1/287:14 pm
SDF
-
STT
2 stops20h 51m
American Airlines
Mon 2/24:47 pm
STT
-
SDF
1 stop8h 12m
American Airlines
Deal found 1/12$372
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/181:19 pm
SDF
-
STT
1 stop24h 12m
Multiple Airlines
Sun 2/225:40 pm
STT
-
SDF
1 stop16h 00m
Multiple Airlines
Deal found 1/12$373

Cheapflights Fare Finder

 
Customize your flight search to find flights from Louisville 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 January 14, 2026.
Use the filters below to find and compare flights from Louisville to Caribbean that are best for you.

Fly from

Louisville

Fly to

Caribbean

Route

Depart

Return

Price

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 2/23

1:19 pm-11:09 pm

1 stop8h 50m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:00 am-12:21 pm

1 stop7h 21m

$223

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Tue 2/17

6:10 am-4:28 pm

1 stop9h 18m

San Juan Luis Munoz Marin Intl

Tue 2/24

7:00 am-11:59 pm

1 stop17h 59m

$226

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 2/23

7:00 am-6:11 pm

2 stops10h 11m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:00 am-3:03 pm

1 stop10h 03m

$246

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 3/9

2:35 pm-9:22 pm

1 stop6h 47m

San Juan Luis Munoz Marin Intl

Tue 3/10

1:05 am-1:17 pm

2 stops12h 12m

$271

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Thu 1/29

11:08 am-8:50 pm

2 stops8h 42m

San Juan Luis Munoz Marin Intl

Sat 2/7

6:05 am-11:19 pm

1 stop18h 14m

$286

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Fri 1/30

8:07 am-9:39 pm

1 stop12h 32m

San Juan Luis Munoz Marin Intl

Fri 2/6

8:20 am-6:39 pm

2 stops11h 19m

$286

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Thu 4/30

12:56 pm-10:05 pm

1 stop9h 09m

San Juan Luis Munoz Marin Intl

Sun 5/3

4:30 pm-8:38 am

1 stop16h 08m

$286

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 3/2

6:15 am-2:40 pm

1 stop7h 25m

San Juan Luis Munoz Marin Intl

Wed 3/4

2:05 am-1:17 pm

2 stops12h 12m

$316

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Tue 5/26

11:00 am-8:34 pm

1 stop9h 34m

San Juan Luis Munoz Marin Intl

Sat 5/30

7:20 am-2:47 pm

1 stop7h 27m

$329

LouisvilleSaint Thomas Island

SDF - STT

SDFSTT

Louisville Intl

Wed 2/18

1:19 pm-2:31 pm

1 stop24h 12m

Saint Thomas Island Cyril E King

Sun 2/22

3:36 pm-12:21 pm

1 stop21h 45m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/12

Showing 1-10 of 49 results
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Best time to book a flight from Louisville to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Louisville 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 Louisville to Caribbean

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

Currently, February is the cheapest month in which you can book a flight from Louisville to Caribbean (average of $148). Flying from Louisville to Caribbean in June is currently the most expensive (average of $252). 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.

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 January 14, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Louisville to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,257 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,040 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,156 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,118 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,309 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Louisville 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 Louisville to Caribbean?

    If you book a flight to Caribbean from Louisville, you will be flying from Louisville Intl, which is the city’s only airport. Louisville Intl (SDF) is located 5.3 mi from the center of Louisville.

  • How long is the flight from Louisville to Caribbean?

    A quick flight from Louisville to Caribbean can take about 8h 11m. Spirit Airlines provides one of the quickest options available for as low as $372. There are 1854 mi between Louisville and Caribbean. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Louisville to Caribbean one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $102. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from Louisville to Caribbean for a low price.

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

    The most popular route from Louisville to Caribbean is Louisville Intl - San Juan Luis Munoz Marin Intl. You may also consider Louisville Intl - Punta Cana or Louisville Intl - Saint Thomas Island Cyril E King.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Louisville 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 Louisville to Caribbean?

    Currently, February is the cheapest month in which you can book a flight from Louisville to Caribbean (average of $148). Flying from Louisville to Caribbean in June is currently the most expensive (average of $252). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Louisville to Caribbean

Discover the top 5 airlines that operate flights from Louisville 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 January 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$402FlexibilityNo cancel feeOn-time65%
DeltaCheapest$215Average$616FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$225Average$661FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$255Average$607FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$259Average$574FlexibilityNo cancel feeOn-time69%

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