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Caribbean Islands

$135+ Cheap flights from Louisville (SDF) to Caribbean Islands

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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Louisville to Caribbean Islands

Cheapest flights from Louisville to Caribbean Islands
Explore the most affordable flight options available from Louisville to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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 11/56:50 amSDF - SJU
1 stop16h 02mAmerican Airlines
Wed 11/196:25 amSJU - SDF
2 stops10h 07mAmerican Airlines
Deal found 10/28$265
This American Airlines deal was found by Cheapflights users on 10/30. 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 12/58:47 amSDF - SJU
1 stop12h 22mAmerican Airlines
Mon 12/84:41 pmSJU - SDF
1 stop6h 08mAmerican Airlines
Deal found 10/30$285
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/147:13 pmSDF - SJU
1 stop16h 52mAmerican Airlines
Wed 11/196:25 amSJU - SDF
1 stop16h 15mAmerican Airlines
Deal found 10/28$290
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/76:15 amSDF - SJU
1 stop13h 33mAmerican Airlines
Sat 11/86:25 amSJU - SDF
1 stop16h 15mAmerican Airlines
Deal found 10/28$300
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Wed 11/59:00 amSDF - SJU
2 stops12h 22mUnited Airlines
Sat 11/158:30 amSJU - SDF
1 stop7h 15mUnited Airlines
Deal found 10/29$305
This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:55 amSDF - SJU
1 stop11h 50mSpirit Airlines
Sun 12/74:10 amSJU - SDF
1 stop7h 50mSpirit Airlines
Deal found 10/30$327
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/511:19 amSDF - SJU
2 stops11h 33mAmerican Airlines
Wed 11/1211:13 amSJU - SDF
2 stops11h 26mAmerican Airlines
Deal found 10/29$330
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/147:00 amSDF - SJU
1 stop15h 52mAmerican Airlines
Sun 12/216:00 amSJU - SDF
1 stop12h 19mAmerican Airlines
Deal found 10/28$334
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 12/47:15 amSDF - NAS
1 stop8h 28mDelta
Thu 12/115:08 pmNAS - SDF
1 stop6h 51mDelta
Deal found 10/28$377
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/276:00 amSDF - NAS
1 stop7h 30mDelta
Thu 12/41:06 pmNAS - SDF
2 stops10h 53mDelta
Deal found 10/28$381
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Fri 12/511:55 amSDF - PUJ
1 stop27h 55mSpirit Airlines
Sun 12/146:08 pmPUJ - SDF
1 stop17h 52mSpirit Airlines
Deal found 10/28$389
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 12/711:55 amSDF - PUJ
1 stop27h 55mMultiple Airlines
Sat 12/136:08 pmPUJ - SDF
2 stops39h 50mMultiple Airlines
Deal found 10/29$403

Cheap flight deals from Louisville to Caribbean Islands

Keep the following information in mind while searching for Louisville to Caribbean Islands flight deals. Data was last updated October 30, 2025.

Round-trip from

$225
(American Airlines)

One-way from

$135
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$344
From Louisville Intl to Caribbean Islands
Search Deals
One-way flight from Louisville Intl to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Louisville to Caribbean Islands 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 October 30, 2025.
Use the filters below to find and compare flights from Louisville to Caribbean Islands that are best for you.

Fly from

Louisville

Fly to

Caribbean Islands

Route

Depart

Return

Price

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sun 2/1

4:15 pm-12:05 am

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Sat 2/28

6:05 am-12:40 pm

1 stop7h 35m

$265

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sat 11/15

9:00 am-10:22 pm

2 stops12h 22m

San Juan Luis Munoz Marin Intl

Wed 11/19

2:20 pm-11:54 pm

1 stop10h 34m

$305

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Wed 4/8

5:34 am-1:40 pm

1 stop8h 06m

San Juan Luis Munoz Marin Intl

Wed 4/15

3:50 pm-11:41 pm

1 stop7h 51m

$305

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sat 11/15

6:00 am-12:46 pm

1 stop5h 46m

San Juan Luis Munoz Marin Intl

Wed 11/19

6:36 pm-12:06 am

1 stop6h 30m

$305

LouisvilleSaint Thomas Island

SDF - STT

SDFSTT

Louisville Intl

Thu 1/8

6:00 am-3:11 pm

1 stop8h 11m

Saint Thomas Island Cyril E King

Sun 1/11

4:06 pm-11:45 pm

1 stop8h 39m

$310

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Tue 3/3

9:00 am-10:22 pm

2 stops12h 22m

San Juan Luis Munoz Marin Intl

Wed 3/4

8:10 am-2:47 pm

1 stop7h 37m

$310

LouisvilleSaint Thomas Island

SDF - STT

SDFSTT

Louisville Intl

Fri 1/9

6:00 am-3:11 pm

1 stop8h 11m

Saint Thomas Island Cyril E King

Mon 1/12

4:06 pm-11:45 pm

1 stop8h 39m

$310

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sun 1/25

2:05 pm-6:11 am

2 stops15h 06m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:05 am-1:28 pm

2 stops12h 23m

$315

LouisvilleSaint Thomas Island

SDF - STT

SDFSTT

Louisville Intl

Fri 1/9

6:54 pm-3:11 pm

2 stops19h 17m

Saint Thomas Island Cyril E King

Mon 1/12

4:06 pm-11:45 pm

1 stop8h 39m

$342

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sun 2/1

6:00 am-4:36 pm

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Fri 2/27

2:05 am-1:28 pm

2 stops12h 23m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 55 results
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Best time to book a flight from Louisville to Caribbean Islands

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

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

Currently, January is the cheapest month in which you can book a flight from Louisville to Caribbean Islands (average of $128). Flying from Louisville to Caribbean Islands in June is currently the most expensive (average of $244). 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 SDF to EPX?

Find hourly flight availability from Louisville to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

It’s typically best to fly out from Louisville to Caribbean Islands in the evening. Doing so could potentially save you 34% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest day to fly from Louisville to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Louisville to Caribbean Islands. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Louisville to Caribbean Islands flight should consider departing on Thursday evenings when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated October 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Louisville to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

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

    Louisville Intl (SDF) is the airport you will fly out of if you book a flight from Louisville to Caribbean Islands. It is only a 5.3 mi journey to Louisville Intl (SDF) from Louisville’s city center.

  • How long is the flight from Louisville to Caribbean Islands?

    There are many flights that can get you from Louisville to Caribbean Islands in 6h 50m. Fly via Southwest, United Airlines, or American Airlines to get the fastest option. Louisville and Caribbean Islands are separated by a distance of 1807 mi. This flight may include one or multiple stops.

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

    The cheapest airlines for a one-way flight from Louisville to Caribbean Islands are American Airlines ($153), Spirit Airlines ($174), and Southwest ($241).

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

    While some choose either Louisville Intl - Punta Cana or Louisville Intl - Providenciales, Louisville Intl - San Juan Luis Munoz Marin Intl is the most popular route from Louisville to Caribbean Islands.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Louisville to Caribbean Islands (average of $128). Flying from Louisville to Caribbean Islands in June is currently the most expensive (average of $244). 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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Top 5 airlines flying from Louisville to Caribbean Islands

Discover the top 5 airlines that operate flights from Louisville to Caribbean Islands. 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$393FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$225Average$692FlexibilityNo cancel feeOn-time63%
DeltaCheapest$225Average$559FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$257Average$575FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$615FlexibilityNo cancel feeOn-time69%

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