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Caribbean

$113+ 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 26 — Jan 21
Fri 12/26
Fri 1/2
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 26, 2025.

Round-trip from

$209
(CheapOair)

One-way from

$113
(Delta)

Popular in

December

Cheapest in

September

Average price

$441
From Louisville Intl to Caribbean
Search Deals
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 26, 2025.

This CheapOair deal was found by Cheapflights users on 11/25. 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
Thu 12/114:10 amSJU - SDF
1 stop7h 50mSpirit Airlines
Deal found 11/25$209
This Mytrip deal was found by Cheapflights users on 11/25. 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.
Mon 12/811:21 amSDF - SJU
1 stop12h 24mMultiple Airlines
Thu 12/114:10 amSJU - SDF
1 stop7h 50mMultiple Airlines
Deal found 11/25$238
This Cheapflightsfares deal was found by Cheapflights users on 11/23. 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 12/1511:55 amSDF - SJU
1 stop11h 50mSpirit Airlines
Fri 12/196:28 pmSJU - SDF
1 stop6h 31mSpirit Airlines
Deal found 11/23$241
This Kiwi.com deal was found by Cheapflights users on 11/23. 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 12/1211:21 amSDF - SJU
1 stop12h 24mMultiple Airlines
Mon 12/226:00 amSJU - SDF
1 stop18h 59mMultiple Airlines
Deal found 11/23$243
This Cheapflightsfares deal was found by Cheapflights users on 11/26. 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
Sun 12/74:10 amSJU - SDF
1 stop7h 50mSpirit Airlines
Deal found 11/26$256
This Kiwi.com deal was found by Cheapflights users on 11/23. 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 12/1211:21 amSDF - SJU
1 stop12h 24mMultiple Airlines
Thu 12/188:20 amSJU - SDF
1 stop16h 39mMultiple Airlines
Deal found 11/23$260
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/1511:21 amSDF - SJU
1 stop12h 24mMultiple Airlines
Sat 12/207:35 amSJU - SDF
1 stop17h 24mMultiple Airlines
Deal found 11/25$261
This Kiwi.com deal was found by Cheapflights users on 11/23. 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 12/1511:21 amSDF - SJU
1 stop12h 24mMultiple Airlines
Mon 12/226:00 amSJU - SDF
1 stop18h 59mMultiple Airlines
Deal found 11/23$263
This American Airlines deal was found by Cheapflights users on 11/26. 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
Fri 12/192:31 pmSJU - SDF
1 stop10h 28mAmerican Airlines
Deal found 11/26$265
This Cheapflightsfares deal was found by Cheapflights users on 11/25. 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 12/1211:55 amSDF - SJU
1 stop11h 50mSpirit Airlines
Sun 12/216:28 pmSJU - SDF
1 stop6h 31mSpirit Airlines
Deal found 11/25$267
This Mytrip deal was found by Cheapflights users on 11/25. 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.
Mon 12/811:55 amSDF - PUJ
2 stops21h 41mMultiple Airlines
Thu 12/113:08 pmPUJ - SDF
2 stops20h 52mMultiple Airlines
Deal found 11/25$344
This Kiwi.com deal was found by Cheapflights users on 11/25. 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.
Tue 12/235:05 amSDF - STT
1 stop29h 26mSpirit Airlines
Mon 12/2912:31 pmSTT - SDF
1 stop12h 28mSpirit Airlines
Deal found 11/25$368

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 26, 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

Sat 1/31

5:30 pm-12:10 am

1 stop5h 40m

San Juan Luis Munoz Marin Intl

Thu 2/5

6:10 am-12:45 pm

1 stop7h 35m

$211

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 1/26

5:35 am-5:17 pm

1 stop10h 42m

San Juan Luis Munoz Marin Intl

Thu 1/29

3:20 pm-9:15 pm

1 stop6h 55m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Tue 1/27

5:35 am-1:06 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

Tue 2/3

6:27 pm-11:50 pm

1 stop6h 23m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sat 1/31

5:35 am-1:05 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

Thu 2/5

6:27 pm-11:50 pm

1 stop6h 23m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Tue 5/19

7:30 am-8:38 pm

2 stops13h 08m

San Juan Luis Munoz Marin Intl

Wed 5/27

7:20 am-2:47 pm

1 stop7h 27m

$250

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Thu 1/29

10:13 am-8:58 pm

1 stop9h 45m

San Juan Luis Munoz Marin Intl

Sat 2/7

6:34 pm-11:50 pm

1 stop6h 16m

$265

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Tue 1/13

6:00 am-2:31 pm

1 stop7h 31m

San Juan Luis Munoz Marin Intl

Tue 1/20

7:30 am-2:36 pm

1 stop8h 06m

$265

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sat 1/31

1:50 pm-12:36 am

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Wed 2/4

2:05 am-1:28 pm

2 stops12h 23m

$277

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 1/26

5:35 am-3:40 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:05 am-1:28 pm

2 stops12h 23m

$301

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Fri 1/23

6:54 pm-2:14 pm

1 stop18h 20m

Simpson Bay Princess Juliana

Thu 1/29

3:09 pm-6:04 pm

1 stop27h 55m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 55 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 26, 2025.

It’s optimal to fly from Louisville to Caribbean in the evening. By choosing this option you can save up to 35% 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 26, 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
4,254 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

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
7,999 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

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
9,046 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

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
11,038 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

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
8,158 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

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 5h 40m. Southwest provides one of the quickest options available for as low as $211. There are 1807 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 Delta, with whom users have recently found tickets for as low as $113. However, be on the lookout for offers from American Airlines and Copa Airlines, 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 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$393FlexibilityNo cancel feeOn-time65%
DeltaCheapest$220Average$579FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$225Average$692FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$255Average$598FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$259Average$614FlexibilityNo cancel feeOn-time69%

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