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Simpson Bay

$167+ Cheap flights from Kentucky to Simpson Bay (SXM)

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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SXM
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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Cheap flight deals from Kentucky to Simpson Bay

Keep the following information in mind while searching for Kentucky to Simpson Bay flight deals. Data was last updated octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$359
(Priceline)

One-way from

$167
(KAYAK)

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 Kentucky to Simpson Bay Princess Juliana
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One-way flight from Kentucky 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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Find flight deals from Kentucky to Simpson Bay

Cheapest flights from Kentucky to Simpson Bay
Explore the most affordable flight options available from Kentucky to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 30, 2025.

This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/126:10 amBNA - SXM
1 stop6h 05mSpirit Airlines
vie. 12/193:20 pmSXM - BNA
1 stop9h 07mSpirit Airlines
Deal found 10/28$359
This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/148:59 pmBNA - SXM
1 stop15h 16mMultiple Airlines
dom. 12/213:40 pmSXM - BNA
1 stop25h 25mMultiple Airlines
Deal found 10/30$412
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/218:38 pmBNA - SXM
1 stop15h 37mSpirit Airlines
sáb. 12/273:20 pmSXM - BNA
1 stop9h 07mSpirit Airlines
Deal found 10/28$472
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/1211:27 amBNA - SXM
3 stops24h 48mMultiple Airlines
vie. 12/195:00 pmSXM - BNA
2 stops24h 05mMultiple Airlines
Deal found 10/28$493
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
vie. 11/219:25 pmCVG - SXM
2 stops15h 50mMultiple Airlines
lun. 11/243:20 pmSXM - CVG
1 stop21h 00mMultiple Airlines
Deal found 10/29$495
This FlightHub deal was found by Cheapflights users on 10/30. 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.
dom. 12/146:40 pmCVG - SXM
1 stop20h 20mAir Canada
jue. 12/183:40 pmSXM - CVG
2 stops27h 20mAir Canada
Deal found 10/30$507
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.
dom. 12/148:41 amCVG - SXM
1 stop6h 44mAmerican Airlines
jue. 12/183:28 pmSXM - CVG
1 stop10h 31mAmerican Airlines
Deal found 10/28$591
This KAYAK deal was found by Cheapflights users on 10/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/206:10 amBNA - SXM
1 stop6h 05mSpirit Airlines
sáb. 12/273:20 pmSXM - BNA
1 stop9h 07mSpirit Airlines
Deal found 10/29$597
This CheapOair deal was found by Cheapflights users on 10/30. 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.
dom. 11/25:09 amBNA - SXM
1 stop8h 29mJetBlue
vie. 11/75:44 pmSXM - BNA
1 stop29h 23mJetBlue
Deal found 10/30$606
This American Airlines deal was found by Cheapflights users on 10/29. 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.
sáb. 12/136:06 pmCVG - SXM
2 stops19h 14mAmerican Airlines
sáb. 12/201:39 pmSXM - CVG
2 stops11h 52mAmerican Airlines
Deal found 10/29$621
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
lun. 12/111:43 amCVG - SXM
2 stops24h 02mMultiple Airlines
sáb. 12/63:20 pmSXM - CVG
1 stop30h 05mMultiple Airlines
Deal found 10/29$636
This Delta deal was found by Cheapflights users on 10/29. 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.
mié. 11/266:00 amCVG - SXM
1 stop7h 55mDelta
mié. 12/33:53 pmSXM - CVG
1 stop9h 11mDelta
Deal found 10/29$651

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky 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 octubre 30, 2025.
Use the filters below to find and compare flights from Kentucky to Simpson Bay that are best for you.

Fly from

Kentucky

Fly to

Simpson Bay

Route

Depart

Return

Price

NashvilleSimpson Bay

BNA - SXM

BNASXM

Nashville Intl

vie. 12/12

6:10 am-2:15 pm

1 stop6h 05m

Simpson Bay Princess Juliana

vie. 12/19

3:20 pm-10:27 pm

1 stop9h 07m

$359

HuntingtonSimpson Bay

HTS - SXM

HTSSXM

Huntington Tri State

mar. 4/14

6:46 am-12:45 pm

1 stop5h 59m

Simpson Bay Princess Juliana

mar. 4/21

2:35 pm-10:30 am

1 stop19h 55m

$405

NashvilleSimpson Bay

BNA - SXM

BNASXM

Nashville Intl

jue. 1/1

8:38 pm-2:15 pm

1 stop15h 37m

Simpson Bay Princess Juliana

lun. 1/12

4:28 pm-10:54 pm

1 stop8h 26m

$405

NashvilleSimpson Bay

BNA - SXM

BNASXM

Nashville Intl

dom. 12/14

8:59 pm-2:15 pm

1 stop15h 16m

Simpson Bay Princess Juliana

dom. 12/21

3:40 pm-3:05 pm

1 stop25h 25m

$412

NashvilleSimpson Bay

BNA - SXM

BNASXM

Nashville Intl

vie. 1/16

8:15 am-4:00 pm

1 stop29h 45m

Simpson Bay Princess Juliana

sáb. 1/31

4:28 pm-10:54 pm

1 stop8h 26m

$432

NashvilleSimpson Bay

BNA - SXM

BNASXM

Nashville Intl

sáb. 1/17

9:50 am-1:15 pm

1 stop25h 25m

Simpson Bay Princess Juliana

dom. 2/1

5:36 pm-10:10 am

1 stop18h 34m

$460

NashvilleSimpson Bay

BNA - SXM

BNASXM

Nashville Intl

dom. 12/21

8:38 pm-2:15 pm

1 stop15h 37m

Simpson Bay Princess Juliana

sáb. 12/27

3:20 pm-10:27 pm

1 stop9h 07m

$472

HuntingtonSimpson Bay

HTS - SXM

HTSSXM

Huntington Tri State

lun. 4/6

10:59 am-1:10 pm

2 stops26h 11m

Simpson Bay Princess Juliana

jue. 4/9

3:55 pm-10:30 am

2 stops18h 35m

$500

CincinnatiSimpson Bay

CVG - SXM

CVGSXM

Cincinnati Cinci./N. Kentucky

dom. 12/14

6:40 pm-4:00 pm

1 stop20h 20m

Simpson Bay Princess Juliana

jue. 12/18

3:40 pm-6:00 pm

2 stops27h 20m

$507

CincinnatiSimpson Bay

CVG - SXM

CVGSXM

Cincinnati Cinci./N. Kentucky

sáb. 1/24

6:40 pm-2:40 pm

2 stops19h 00m

Simpson Bay Princess Juliana

sáb. 1/31

5:00 pm-6:00 pm

1 stop26h 00m

$552

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 27 results
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Best time to book a flight from Kentucky to Simpson Bay

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

How much does it cost to fly round-trip from Kentucky to Simpson Bay?

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Simpson Bay. 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 into for flights to Simpson Bay from Kentucky?

    Most people fly into Simpson Bay Princess Juliana (SXM) if they book a flight to Simpson Bay from Kentucky. Princess Juliana is conveniently located just 0.5 mi from Simpson Bay’s city center.

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

    There are many flights that can get you from Kentucky to Simpson Bay in 5h 59m. Fly via Spirit Airlines, American Airlines, or Air Canada to get the fastest option. The distance between Kentucky and Simpson Bay is about 1827 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Kentucky to Simpson Bay?

    Most travelers choose Cincinnati Cinci./N. Kentucky - Simpson Bay Princess Juliana, Nashville Intl - Simpson Bay Princess Juliana or Lexington Blue Grass - Simpson Bay Princess Juliana when deciding on the best route from Kentucky to Simpson Bay.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Kentucky 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.

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 Kentucky to Simpson Bay

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Top 2 airlines flying from Kentucky to Simpson Bay

Discover the top 2 airlines that operate flights from Kentucky 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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$551Average$690FlexibilityNo cancel feeOn-time71%
DeltaCheapest$586Average$699FlexibilityNo cancel feeOn-timeN/A

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