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$103+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$205
(American Airlines)

One-way from

$109
(American Airlines)

Popular in

December

Cheapest in

October

Average price

$467
From Louisville Intl to Caribbean
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One-way flight from Louisville Intl to Caribbean
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Highest demand for flights based on searches. 0% potential increase in price ($3 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 August 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 August 14, 2025.

This United Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 10/256:15 amSDF - SJU
1 stop7h 30mUnited Airlines
Fri 10/311:05 amSJU - SDF
2 stops12h 12mUnited Airlines
Deal found 8/14$205
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Sat 10/117:26 amSDF - SJU
1 stop15h 39mAmerican Airlines
Sat 10/187:10 amSJU - SDF
1 stop15h 21mAmerican Airlines
Deal found 8/13$230
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Sun 11/25:00 amSDF - SJU
1 stop8h 02mAmerican Airlines
Sat 11/86:25 amSJU - SDF
1 stop16h 14mAmerican Airlines
Deal found 8/13$235
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/18:10 amSDF - SJU
1 stop8h 21mDelta
Tue 10/75:43 pmSJU - SDF
1 stop6h 16mDelta
Deal found 8/12$238
This Southwest deal was found by Cheapflights users on 8/14. 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.
Thu 10/25:30 pmSDF - SJU
1 stop7h 15mSouthwest
Sun 10/55:45 amSJU - SDF
1 stop6h 45mSouthwest
Deal found 8/14$245
This American Airlines deal was found by Cheapflights users on 8/14. 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 11/236:50 amSDF - SJU
1 stop15h 57mAmerican Airlines
Wed 11/263:53 pmSJU - SDF
1 stop8h 06mAmerican Airlines
Deal found 8/14$255
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:48 pmSDF - SJU
1 stop9h 12mDelta
Wed 10/82:31 pmSJU - SDF
1 stop7h 17mDelta
Deal found 8/12$260
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/169:31 pmSDF - STT
1 stop12h 18mSpirit Airlines
Thu 10/232:01 pmSTT - SDF
1 stop8h 56mSpirit Airlines
Deal found 8/12$262
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Sat 10/47:09 pmSDF - SJU
2 stops16h 02mAmerican Airlines
Wed 10/83:00 pmSJU - SDF
1 stop18h 30mAmerican Airlines
Deal found 8/14$265
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/78:23 amSDF - SJU
2 stops29h 48mSpirit Airlines
Thu 9/1111:59 amSJU - SDF
1 stop10h 05mSpirit Airlines
Deal found 8/13$267
This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/68:23 amSDF - STT
1 stop25h 21mSpirit Airlines
Sat 9/1310:49 amSTT - SDF
1 stop11h 15mSpirit Airlines
Deal found 8/14$268
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/18:10 amSDF - SJU
1 stop8h 21mDelta
Thu 10/95:43 pmSJU - SDF
1 stop6h 16mDelta
Deal found 8/12$271

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 August 14, 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 10/4

3:10 pm-11:45 pm

1 stop8h 35m

San Juan Luis Munoz Marin Intl

Thu 10/9

5:50 am-12:35 pm

1 stop6h 45m

$205

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Wed 10/1

7:09 pm-12:47 pm

2 stops17h 38m

San Juan Luis Munoz Marin Intl

Mon 10/6

3:00 pm-9:30 am

1 stop18h 30m

$205

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sat 10/25

6:15 am-1:45 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Fri 10/31

1:20 pm-11:40 pm

1 stop10h 20m

$205

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sat 10/4

3:10 pm-11:45 pm

1 stop8h 35m

San Juan Luis Munoz Marin Intl

Wed 10/8

6:10 am-1:00 pm

1 stop6h 50m

$205

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 10/13

7:33 am-11:59 pm

1 stop16h 26m

San Juan Luis Munoz Marin Intl

Tue 10/28

7:45 am-5:54 pm

2 stops10h 09m

$205

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 10/20

5:30 pm-12:45 am

1 stop7h 15m

San Juan Luis Munoz Marin Intl

Mon 10/27

5:50 am-7:25 pm

1 stop13h 35m

$205

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Thu 10/16

12:59 pm-11:59 pm

1 stop11h 00m

San Juan Luis Munoz Marin Intl

Wed 10/22

5:00 pm-12:36 am

1 stop7h 36m

$205

LouisvilleSaint Thomas Island

SDF - STT

SDFSTT

Louisville Intl

Thu 10/16

9:31 pm-9:49 am

1 stop12h 18m

Saint Thomas Island Cyril E King

Thu 10/23

2:01 pm-10:57 pm

1 stop8h 56m

$262

LouisvilleSaint Thomas Island

SDF - STT

SDFSTT

Louisville Intl

Sat 9/6

8:23 am-9:44 am

1 stop25h 21m

Saint Thomas Island Cyril E King

Sat 9/13

10:49 am-10:04 pm

1 stop11h 15m

$268

LouisvilleSaint Thomas Island

SDF - STT

SDFSTT

Louisville Intl

Wed 10/15

5:31 pm-9:56 am

1 stop16h 25m

Saint Thomas Island Cyril E King

Sun 10/19

11:01 am-6:03 pm

1 stop7h 02m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

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, September is the cheapest month in which you can book a flight from Louisville to Caribbean (average of $254). Flying from Louisville to Caribbean in June is currently the most expensive (average of $339). 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 August 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Louisville to Caribbean as you normally would.

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 August 14, 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
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,046 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • 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 $109. However, be on the lookout for offers from Spirit Airlines and United 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 - Santiago de los Caballeros.

  • 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, September is the cheapest month in which you can book a flight from Louisville to Caribbean (average of $254). Flying from Louisville to Caribbean in June is currently the most expensive (average of $339). 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$389FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$225Average$643FlexibilityNo cancel feeOn-time63%
DeltaCheapest$225Average$562FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$265Average$604FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$316Average$654FlexibilityNo cancel feeOn-time69%

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