HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$544+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SXM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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

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 September 11, 2025.

Round-trip from

$544
(Kiwi.com)

Popular in

June

Cheapest in

December
From Louisville Intl to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($135 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($33 potential savings vs. average RT price).
Search Deals

Find 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Sat 10/257:15 amSDF - SXM
2 stops28h 16mMultiple Airlines
Sat 11/13:05 pmSXM - SDF
1 stop27h 58mMultiple Airlines
Deal found 9/10$544
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/255:53 pmSDF - SXM
2 stops21h 22mAmerican Airlines
Sat 11/12:40 pmSXM - SDF
2 stops21h 48mAmerican Airlines
Deal found 9/10$614
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/106:00 amSDF - SXM
1 stop7h 37mAmerican Airlines
Fri 10/174:24 pmSXM - SDF
1 stop8h 12mAmerican Airlines
Deal found 9/9$717
This American Airlines deal was found by Cheapflights users on 9/10. 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 9/275:32 pmSDF - SXM
2 stops19h 47mAmerican Airlines
Sat 10/42:20 pmSXM - SDF
2 stops19h 04mAmerican Airlines
Deal found 9/10$761

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 September 11, 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

Sat 10/25

7:15 am-11:31 am

2 stops28h 16m

Simpson Bay Princess Juliana

Sat 11/1

3:05 pm-7:03 pm

1 stop27h 58m

$544

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Sun 1/18

10:55 am-3:10 pm

1 stop27h 15m

Simpson Bay Princess Juliana

Fri 1/23

4:28 pm-9:54 am

1 stop18h 26m

$546

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Sun 1/18

6:28 am-3:51 pm

1 stop8h 23m

Simpson Bay Princess Juliana

Fri 1/23

2:52 pm-10:23 am

2 stops20h 31m

$566

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Sun 1/18

7:45 pm-1:55 pm

2 stops17h 10m

Simpson Bay Princess Juliana

Fri 1/23

4:15 pm-10:00 am

2 stops18h 45m

$566

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Mon 3/9

6:00 am-1:53 pm

1 stop7h 53m

Simpson Bay Princess Juliana

Wed 3/11

3:45 pm-11:37 am

2 stops19h 52m

$586

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Sat 1/17

6:24 pm-1:22 pm

1 stop17h 58m

Simpson Bay Princess Juliana

Sat 1/24

4:15 pm-12:17 am

1 stop9h 02m

$586

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Sat 10/25

5:53 pm-3:15 pm

2 stops21h 22m

Simpson Bay Princess Juliana

Sat 11/1

2:40 pm-12:28 pm

2 stops21h 48m

$614

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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, September is the cheapest month in which you can book a flight from Louisville to Simpson Bay (average of $459). Flying from Louisville to Simpson Bay in March is currently the most expensive (average of $652). 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 September 11, 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
8.0
Very good
7,960 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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?

    Spirit Airlines, United Airlines, and American Airlines can get you from Louisville to Simpson Bay in just under 8h 23m. Your travel time can differ by up to 18h 52m. 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 $533 on this airline. An additional option worth looking into is Delta, starting at $543. American Airlines is currently priced 23% 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, September is the cheapest month in which you can book a flight from Louisville to Simpson Bay (average of $459). Flying from Louisville to Simpson Bay in March is currently the most expensive (average of $652). 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$533Average$660FlexibilityNo cancel feeOn-time71%
DeltaCheapest$543Average$692FlexibilityNo 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.