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Simpson Bay

$591+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SXM
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Louisville to Simpson Bay

Best flights from Louisville to Simpson Bay
Discover carefully curated flight deals from Louisville to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 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.
Tue 4/76:44 amSDF - SXM
1 stop8h 31mAmerican Airlines
Mon 4/132:25 pmSXM - SDF
2 stops20h 01mAmerican Airlines
Deal found 10/28$591
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/95:45 pmSDF - SXM
2 stops17h 30mDelta
Wed 3/1112:45 pmSXM - SDF
1 stop8h 07mDelta
Deal found 10/27$596
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.
Sat 1/175:26 pmSDF - SXM
2 stops18h 32mAmerican Airlines
Sat 1/242:30 pmSXM - SDF
1 stop9h 49mAmerican Airlines
Deal found 10/28$616
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.
Sat 1/106:32 pmSDF - SXM
2 stops18h 59mAmerican Airlines
Sat 1/173:31 pmSXM - SDF
1 stop9h 28mAmerican Airlines
Deal found 10/28$616

Cheap 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$591
(American Airlines)

Popular in

June

Cheapest in

December

Average price

$696
Provider with most accurate pricing for Louisville Intl-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Louisville Intl-Simpson Bay Princess Juliana flights.
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From Louisville Intl to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 12% potential increase in price ($101 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
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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 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 October 30, 2025.
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

Tue 4/7

6:44 am-3:15 pm

1 stop8h 31m

Simpson Bay Princess Juliana

Mon 4/13

2:25 pm-10:26 am

2 stops20h 01m

$591

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Mon 3/9

5:45 pm-11:15 am

2 stops17h 30m

Simpson Bay Princess Juliana

Wed 3/11

12:45 pm-8:52 pm

1 stop8h 07m

$596

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Sat 1/17

5:26 pm-12:58 pm

2 stops18h 32m

Simpson Bay Princess Juliana

Sat 1/24

2:30 pm-11:19 pm

1 stop9h 49m

$616

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Sat 1/10

6:32 pm-2:31 pm

2 stops18h 59m

Simpson Bay Princess Juliana

Sat 1/17

3:31 pm-11:59 pm

1 stop9h 28m

$616

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Louisville-Simpson Bay flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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, April is the cheapest month in which you can book a flight from Louisville to Simpson Bay (average of $421). Flying from Louisville to Simpson Bay in July is currently the most expensive (average of $579). 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 October 30, 2025.
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
7,993 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,993 reviews
Delta
7.9
Good
7,993 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,030 reviews
Delta
7.9
Good
7,993 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 Delta can get you from Louisville to Simpson Bay in just under 8h 31m. Your travel time can differ by up to 8h 59m. 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 $551 on this airline. An additional option worth looking into is Delta, starting at $586. American Airlines is currently priced 25% 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, April is the cheapest month in which you can book a flight from Louisville to Simpson Bay (average of $421). Flying from Louisville to Simpson Bay in July is currently the most expensive (average of $579). 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

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Alternative routes for Louisville to Simpson Bay

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$551Average$671FlexibilityNo cancel feeOn-time71%
DeltaCheapest$586Average$699FlexibilityNo cancel feeOn-timeN/A

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