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$115+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
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 November 13, 2025.

Round-trip from

$225
(American Airlines)

One-way from

$115
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$445
From Louisville Intl to Caribbean
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One-way flight from Louisville Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($28 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).
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Average for round-trip flights in November 2025
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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 November 13, 2025.

This American Airlines deal was found by Cheapflights users on 11/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:47 amSDF - SJU
1 stop12h 22mAmerican Airlines
Tue 12/166:00 amSJU - SDF
2 stops10h 35mAmerican Airlines
Deal found 11/11$225
This Priceline deal was found by Cheapflights users on 11/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/811:55 amSDF - SJU
1 stop11h 50mSpirit Airlines
Thu 12/114:10 amSJU - SDF
1 stop7h 50mSpirit Airlines
Deal found 11/11$237
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/811:55 amSDF - SJU
2 stops35h 21mMultiple Airlines
Thu 12/114:10 amSJU - SDF
1 stop7h 21mMultiple Airlines
Deal found 11/11$279
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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.
Fri 12/511:55 amSDF - SJU
1 stop11h 50mSpirit Airlines
Sat 12/64:10 amSJU - SDF
1 stop7h 50mSpirit Airlines
Deal found 11/11$283
This American Airlines deal was found by Cheapflights users on 11/12. 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.
Fri 12/56:15 amSDF - SJU
1 stop5h 46mAmerican Airlines
Mon 12/86:25 amSJU - SDF
1 stop16h 17mAmerican Airlines
Deal found 11/12$285
This American Airlines deal was found by Cheapflights users on 11/12. 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 11/276:25 amSDF - SJU
1 stop8h 29mAmerican Airlines
Mon 12/16:25 amSJU - SDF
1 stop16h 15mAmerican Airlines
Deal found 11/12$305
This Southwest deal was found by Cheapflights users on 11/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/81:50 pmSDF - SJU
2 stops9h 45mSouthwest
Fri 12/1211:55 amSJU - SDF
2 stops10h 35mSouthwest
Deal found 11/11$325
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/147:00 amSDF - SJU
1 stop7h 57mAmerican Airlines
Wed 12/1712:49 pmSJU - SDF
2 stops10h 20mAmerican Airlines
Deal found 11/12$342
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:55 amSDF - SJU
1 stop11h 50mMultiple Airlines
Sun 12/711:05 amSJU - SDF
2 stops24h 55mMultiple Airlines
Deal found 11/11$346
This American Airlines deal was found by Cheapflights users on 11/13. 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 12/48:06 pmSDF - STT
1 stop15h 50mAmerican Airlines
Tue 12/96:17 pmSTT - SDF
2 stops17h 23mAmerican Airlines
Deal found 11/13$371
This American Airlines deal was found by Cheapflights users on 11/12. 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 12/46:25 amSDF - NAS
1 stop5h 48mAmerican Airlines
Thu 12/1111:09 amNAS - SDF
1 stop12h 45mAmerican Airlines
Deal found 11/12$377
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1111:55 amSDF - PUJ
1 stop27h 55mMultiple Airlines
Thu 12/186:08 pmPUJ - SDF
1 stop27h 10mMultiple Airlines
Deal found 11/11$396

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 November 13, 2025.
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

Sun 1/11

6:12 pm-6:11 am

2 stops10h 59m

San Juan Luis Munoz Marin Intl

Fri 1/16

2:05 am-1:28 pm

2 stops12h 23m

$307

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Tue 3/3

2:35 pm-10:22 pm

1 stop6h 47m

San Juan Luis Munoz Marin Intl

Wed 3/4

8:10 am-2:47 pm

1 stop7h 37m

$310

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sun 1/25

8:29 am-10:22 pm

2 stops12h 53m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:05 am-1:28 pm

2 stops12h 23m

$315

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sat 1/31

2:05 pm-6:11 am

2 stops15h 06m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:05 am-1:28 pm

2 stops12h 23m

$315

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Fri 1/23

1:50 pm-12:36 am

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:05 am-1:28 pm

2 stops12h 23m

$315

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Thu 1/15

7:00 am-11:56 pm

1 stop15h 56m

San Juan Luis Munoz Marin Intl

Sat 1/17

6:30 am-9:16 pm

1 stop15h 46m

$342

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Thu 4/30

11:15 am-8:06 pm

1 stop8h 51m

San Juan Luis Munoz Marin Intl

Sun 5/3

6:15 am-12:36 pm

1 stop6h 21m

$353

LouisvilleSaint Thomas Island

SDF - STT

SDFSTT

Louisville Intl

Sun 1/11

4:39 pm-2:52 pm

1 stop21h 13m

Saint Thomas Island Cyril E King

Thu 1/15

3:57 pm-1:00 pm

1 stop22h 03m

$353

LouisvilleSaint Thomas Island

SDF - STT

SDFSTT

Louisville Intl

Sun 1/18

4:39 pm-2:52 pm

1 stop21h 13m

Saint Thomas Island Cyril E King

Sat 1/24

6:15 pm-2:33 pm

1 stop21h 18m

$366

LouisvilleSaint Thomas Island

SDF - STT

SDFSTT

Louisville Intl

Thu 12/4

8:06 pm-12:56 pm

1 stop15h 50m

Saint Thomas Island Cyril E King

Tue 12/9

6:17 pm-10:40 am

2 stops17h 23m

$371

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 60 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, January is the cheapest month in which you can book a flight from Louisville to Caribbean (average of $128). Flying from Louisville to Caribbean 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 CB?

Find hourly flight availability from Louisville 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 13, 2025.

It’s optimal to fly from Louisville to Caribbean in the evening. By choosing this option you can save up to 34% on the cost of your flight, compared to a flight in the afternoon.

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

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

Travelers seeking maximum savings on their Louisville to Caribbean 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

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 13, 2025.
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
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

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
8,007 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

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
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

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
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

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
8,139 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

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. 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 7h 30m. United Airlines provides one of the quickest options available for as low as $377. There are 1028 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 American Airlines, with whom users have recently found tickets for as low as $115. However, be on the lookout for offers from Spirit 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 - Providenciales.

  • 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, January is the cheapest month in which you can book a flight from Louisville to Caribbean (average of $128). Flying from Louisville to Caribbean 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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Alternative routes for Louisville to Caribbean

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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$394FlexibilityNo cancel feeOn-time65%
DeltaCheapest$223Average$559FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$225Average$691FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$257Average$570FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$614FlexibilityNo cancel feeOn-time69%

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