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Simpson Bay

$301+ Cheap flights from Kentucky 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SXM
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$301
(Mytrip)

Popular in

June

Cheapest in

October

Average price

$804
From Kentucky to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($165 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 31, 2025.

This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/236:05 amBNA - SXM
1 stop6h 55mSpirit Airlines
Wed 8/273:05 pmSXM - BNA
1 stop17h 07mSpirit Airlines
Deal found 7/30$301
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Fri 9/125:34 pmCVG - SXM
1 stop20h 26mMultiple Airlines
Fri 9/193:05 pmSXM - CVG
1 stop8h 27mMultiple Airlines
Deal found 7/29$374
This FlightHub deal was found by Cheapflights users on 7/30. 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.
Fri 10/108:40 pmSDF - SXM
1 stop17h 20mSpirit Airlines
Fri 10/173:05 pmSXM - SDF
1 stop28h 30mSpirit Airlines
Deal found 7/30$422
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/104:50 pmBNA - SXM
3 stops22h 40mMultiple Airlines
Mon 9/153:05 pmSXM - BNA
1 stop8h 29mMultiple Airlines
Deal found 7/30$443
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 8/237:28 amBNA - SXM
1 stop6h 41mAmerican Airlines
Tue 8/264:30 pmSXM - BNA
1 stop8h 42mAmerican Airlines
Deal found 7/29$457
This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
Sun 9/148:23 amSDF - SXM
1 stop29h 37mMultiple Airlines
Sun 9/2112:25 pmSXM - SDF
2 stops33h 39mMultiple Airlines
Deal found 7/31$542
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/297:05 amCVG - SXM
1 stop6h 45mDelta
Fri 10/33:20 pmSXM - CVG
1 stop7h 20mDelta
Deal found 7/30$561
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 11/56:00 amCVG - SXM
2 stops9h 20mAmerican Airlines
Wed 11/193:20 pmSXM - CVG
2 stops19h 25mAmerican Airlines
Deal found 7/29$566
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/137:16 pmHTS - SXM
2 stops18h 03mAmerican Airlines
Sat 9/202:20 pmSXM - HTS
2 stops21h 20mAmerican Airlines
Deal found 7/30$567
This American Airlines deal was found by Cheapflights users on 7/31. 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 10/105:02 pmSDF - SXM
2 stops20h 35mAmerican Airlines
Fri 10/174:24 pmSXM - SDF
2 stops18h 19mAmerican Airlines
Deal found 7/31$591
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/47:15 pmLEX - SXM
2 stops18h 04mAmerican Airlines
Sat 10/112:40 pmSXM - LEX
2 stops19h 53mAmerican Airlines
Deal found 7/30$617
This United Airlines deal was found by Cheapflights users on 7/31. 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 10/257:33 pmLEX - SXM
1 stop19h 24mUnited Airlines
Sat 11/11:20 pmSXM - LEX
1 stop10h 24mUnited Airlines
Deal found 7/31$755

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 July 31, 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

Sat 8/23

6:05 am-2:00 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Wed 8/27

3:05 pm-7:12 am

1 stop17h 07m

$301

CincinnatiSimpson Bay

CVG - SXM

CVGSXM

Cincinnati Cinci./N. Kentucky

Fri 9/12

5:34 pm-2:00 pm

1 stop20h 26m

Simpson Bay Princess Juliana

Fri 9/19

3:05 pm-11:32 pm

1 stop8h 27m

$374

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Fri 10/10

8:40 pm-2:00 pm

1 stop17h 20m

Simpson Bay Princess Juliana

Fri 10/17

3:05 pm-7:35 pm

1 stop28h 30m

$422

NashvilleSimpson Bay

BNA - SXM

BNASXM

Nashville Intl

Wed 9/10

4:50 pm-4:30 pm

3 stops22h 40m

Simpson Bay Princess Juliana

Mon 9/15

3:05 pm-10:34 pm

1 stop8h 29m

$443

NashvilleSimpson Bay

BNA - SXM

BNASXM

Nashville Intl

Sat 8/23

6:00 am-3:09 pm

1 stop8h 09m

Simpson Bay Princess Juliana

Tue 8/26

2:30 pm-10:21 pm

1 stop8h 51m

$457

LouisvilleSimpson Bay

SDF - SXM

SDFSXM

Louisville Intl

Sun 9/14

8:23 am-2:00 pm

1 stop29h 37m

Simpson Bay Princess Juliana

Sun 9/21

12:25 pm-10:04 pm

2 stops33h 39m

$542

CincinnatiSimpson Bay

CVG - SXM

CVGSXM

Cincinnati Cinci./N. Kentucky

Mon 9/29

7:05 am-1:50 pm

1 stop6h 45m

Simpson Bay Princess Juliana

Fri 10/3

3:20 pm-10:40 pm

1 stop7h 20m

$561

HuntingtonSimpson Bay

HTS - SXM

HTSSXM

Huntington Tri State

Sat 9/13

7:16 pm-1:19 pm

2 stops18h 03m

Simpson Bay Princess Juliana

Sat 9/20

2:20 pm-11:40 am

2 stops21h 20m

$567

LexingtonSimpson Bay

LEX - SXM

LEXSXM

Lexington Blue Grass

Sun 1/18

6:29 pm-12:15 pm

2 stops16h 46m

Simpson Bay Princess Juliana

Fri 1/23

4:26 pm-12:40 pm

2 stops21h 14m

$575

CincinnatiSimpson Bay

CVG - SXM

CVGSXM

Cincinnati Cinci./N. Kentucky

Wed 10/15

6:50 pm-3:15 pm

2 stops20h 25m

Simpson Bay Princess Juliana

Wed 10/29

2:40 pm-10:47 am

2 stops20h 07m

$591

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 19 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
No data available for this route at this time. Please check back soon.

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 July 31, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Kentucky to Simpson Bay to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

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
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

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!
United Airlines
7.4
Good
8,900 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

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
7,981 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

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!
WestJet
7.2
Good
2,978 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

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!
Spirit Airlines
6.3
Okay
8,048 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

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 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.

  • 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.

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

    Currently, September is the cheapest month in which you can book a flight from Kentucky to Simpson Bay (average of $459). Flying from Kentucky to Simpson Bay in March 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

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Alternative routes for Kentucky to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$469Average$655FlexibilityNo cancel feeOn-time71%
DeltaCheapest$543Average$692FlexibilityNo cancel feeOn-timeN/A

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