HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$428+ Cheap flights from Louisville (SDF) to Simpson Bay (SXM)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SXM
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Louisville to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Louisville to Simpson Bay

Cheapest flights from Louisville to Simpson Bay
Explore the most affordable flight options available from Louisville to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Mon 6/89:10 pm
SDF
-
SXM
1 stop16h 06m
Multiple Airlines
Tue 6/162:11 pm
SXM
-
SDF
1 stop21h 19m
Multiple Airlines
Deal found 1/28$428
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Mon 6/89:10 pm
SDF
-
SXM
1 stop16h 06m
Multiple Airlines
Wed 6/172:11 pm
SXM
-
SDF
1 stop24h 27m
Multiple Airlines
Deal found 1/28$498
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Tue 6/93:33 pm
SDF
-
SXM
1 stop21h 43m
Multiple Airlines
Tue 6/162:11 pm
SXM
-
SDF
1 stop21h 19m
Multiple Airlines
Deal found 1/28$537
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Mon 6/89:10 pm
SDF
-
SXM
1 stop16h 06m
Multiple Airlines
Thu 6/182:11 pm
SXM
-
SDF
1 stop30h 19m
Multiple Airlines
Deal found 1/28$560
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Wed 6/1012:20 pm
SDF
-
SXM
1 stop24h 56m
Multiple Airlines
Tue 6/162:11 pm
SXM
-
SDF
1 stop21h 19m
Multiple Airlines
Deal found 1/28$578
This American Airlines deal was found by Cheapflights users on 1/27. 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 7/86:13 am
SDF
-
SXM
1 stop9h 18m
American Airlines
Wed 7/221:45 pm
SXM
-
SDF
1 stop8h 49m
American Airlines
Deal found 1/27$589
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Sat 4/48:00 pm
SDF
-
SXM
1 stop17h 16m
American Airlines
Thu 4/92:24 pm
SXM
-
SDF
2 stops19h 56m
American Airlines
Deal found 1/28$594
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Tue 6/93:33 pm
SDF
-
SXM
1 stop21h 43m
Spirit Airlines
Wed 6/172:11 pm
SXM
-
SDF
1 stop24h 27m
Spirit Airlines
Deal found 1/28$608
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Tue 4/76:01 am
SDF
-
SXM
1 stop7h 15m
American Airlines
Mon 4/132:24 pm
SXM
-
SDF
1 stop10h 01m
American Airlines
Deal found 1/28$614

Find flight deals from Louisville to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Louisville (SDF) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$428
(Kiwi.com)

Popular in

June

Cheapest in

March

Average price

$758
Provider with most accurate pricing for Louisville Intl-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Simpson Bay Princess Juliana flights.
Search Deals
From Louisville Intl to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($120 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Louisville to Simpson Bay 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 29, 2026.
Use the filters below to find and compare flights from Louisville to Simpson Bay that are best for you.

Fly from

Louisville

Fly to

Simpson Bay

Route

Depart

Return

Price

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Mon 6/8

9:10 pm-1:16 pm

1 stop16h 06m

Simpson Bay Princess Juliana

Thu 6/18

2:11 pm-8:30 pm

1 stop30h 19m

$560

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Wed 7/8

6:13 am-3:31 pm

1 stop9h 18m

Simpson Bay Princess Juliana

Wed 7/22

1:45 pm-10:34 pm

1 stop8h 49m

$589

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Mon 6/8

6:00 am-12:33 pm

1 stop6h 33m

Simpson Bay Princess Juliana

Thu 6/18

3:50 pm-9:45 am

2 stops17h 55m

$594

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Mon 6/8

7:20 pm-1:22 pm

2 stops18h 02m

Simpson Bay Princess Juliana

Thu 6/18

4:36 pm-12:46 pm

2 stops20h 10m

$594

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Tue 6/9

6:30 am-2:43 pm

1 stop8h 13m

Simpson Bay Princess Juliana

Tue 6/16

1:35 pm-9:45 am

2 stops20h 10m

$594

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Tue 6/9

3:33 pm-1:16 pm

1 stop21h 43m

Simpson Bay Princess Juliana

Wed 6/17

2:11 pm-2:38 pm

1 stop24h 27m

$608

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Tue 4/7

6:01 am-1:16 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Mon 4/13

2:24 pm-10:08 pm

1 stop7h 44m

$614

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Compare providers for flights from Louisville to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Louisville to Simpson Bay in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Louisville-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Louisville-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Louisville-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Louisville-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Louisville-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Louisville to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay 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 Simpson Bay

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

Currently, March is the cheapest month in which you can book a flight from Louisville to Simpson Bay (average of $376). Flying from Louisville to Simpson Bay in May is currently the most expensive (average of $655). 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 Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. 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 Simpson Bay. Reviews last updated January 29, 2026.
Read through reviews of airlines operating flights from Louisville to Simpson Bay, such as Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,128 reviews

Boarding

8.1

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,128 reviews
Delta
7.9
Good
8,128 reviews

Boarding

8.1

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,205 reviews
Delta
7.9
Good
8,128 reviews

Boarding

8.1

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Louisville to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Louisville to Simpson Bay?

    American Airlines and United Airlines can get you from Louisville to Simpson Bay in just under 6h 33m. Your travel time can differ by up to 2h 45m. The distance between Louisville and Simpson Bay is about 1947 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Louisville to Simpson Bay round-trip?

    Our cheapest airline available from Louisville to Simpson Bay is American Airlines. Our recent data shows that you can find tickets from as low as $576 on this airline. An additional option worth looking into is Delta, starting at $591. American Airlines is currently priced 18% below the average price you’ll pay for this route.

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

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

  • How can I find direct flights from Louisville to Simpson Bay?

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

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

    Yes. Cheapflights offers flight deals from Louisville to Simpson Bay 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 Simpson Bay?

    Currently, March is the cheapest month in which you can book a flight from Louisville to Simpson Bay (average of $376). Flying from Louisville to Simpson Bay in May is currently the most expensive (average of $655). 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

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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.

Alternative routes for Louisville to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
Cincinnati to Simpson Bay flights
Nashville to Simpson Bay flights
Lexington to Simpson Bay flights

Top 2 airlines flying from Louisville to Simpson Bay

Discover the top 2 airlines that operate flights from Louisville to Simpson Bay. 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 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$576Average$684FlexibilityNo cancel feeOn-time71%
DeltaCheapest$591Average$791FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.