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Simpson Bay

$268+ Cheap flights from Charleston (CHS) 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHS — SXM
Feb 1 — Feb 81
Sun 2/1
Sun 2/8
1 adult, Economy
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Cheap flight deals from Charleston to Simpson Bay

Best flights from Charleston to Simpson Bay
Discover carefully curated flight deals from Charleston to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 2, 2026.

This Mytrip deal was found by Cheapflights users on 1/1. 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.
Thu 1/295:05 pmCHS - SXM
3 stops20h 05mSpirit Airlines
Thu 2/53:20 pmSXM - CHS
3 stops25h 50mSpirit Airlines
Deal found 1/1$399
This Expedia deal was found by Cheapflights users on 1/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:20 amCHS - SXM
1 stop25h 50mJetBlue
Mon 3/93:35 pmSXM - CHS
1 stop17h 48mJetBlue
Deal found 1/1$476
This Expedia deal was found by Cheapflights users on 1/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:50 pmCHS - SXM
1 stop16h 39mMultiple Airlines
Sat 4/42:15 pmSXM - CHS
1 stop9h 11mMultiple Airlines
Deal found 1/1$523
This Delta deal was found by Cheapflights users on 1/1. 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.
Tue 3/35:00 pmCHS - SXM
2 stops18h 13mDelta
Tue 3/103:20 pmSXM - CHS
2 stops20h 02mDelta
Deal found 1/1$552
This American Airlines deal was found by Cheapflights users on 12/31. 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.
Sun 5/248:33 pmCHS - SXM
2 stops16h 49mAmerican Airlines
Sat 5/304:36 pmSXM - CHS
2 stops19h 40mAmerican Airlines
Deal found 12/31$556
This Priceline deal was found by Cheapflights users on 1/1. 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.
Fri 3/137:00 amCHS - SXM
1 stop6h 08mSpirit Airlines
Mon 3/162:15 pmSXM - CHS
1 stop9h 11mSpirit Airlines
Deal found 1/1$505
This Kiwi.com deal was found by Cheapflights users on 12/31. 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 5/242:53 pmCHS - SXM
2 stops22h 23mMultiple Airlines
Sat 5/302:11 pmSXM - CHS
1 stop8h 30mMultiple Airlines
Deal found 12/31$527
This Delta deal was found by Cheapflights users on 1/1. 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.
Wed 3/45:27 amCHS - SXM
1 stop8h 23mDelta
Tue 3/103:20 pmSXM - CHS
2 stops20h 02mDelta
Deal found 1/1$552
This American Airlines deal was found by Cheapflights users on 12/31. 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.
Mon 6/18:33 pmCHS - SXM
2 stops18h 58mAmerican Airlines
Sun 6/72:27 pmSXM - CHS
2 stops19h 41mAmerican Airlines
Deal found 12/31$561
This FlightHub deal was found by Cheapflights users on 12/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:05 amCHS - SXM
1 stop27h 00mMultiple Airlines
Mon 5/43:10 pmSXM - CHS
1 stop28h 03mMultiple Airlines
Deal found 12/31$557

Find flight deals from Charleston to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Charleston (CHS) 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 2, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$268
(Kiwi.com)

Popular in

May

Cheapest in

February

Average price

$625
Provider with most accurate pricing for Charleston-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Charleston-Simpson Bay Princess Juliana flights.
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From Charleston to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($104 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($38 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Charleston 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 2, 2026.
Use the filters below to find and compare flights from Charleston to Simpson Bay that are best for you.

Fly from

Charleston

Fly to

Simpson Bay

Route

Depart

Return

Price

CharlestonSimpson Bay

CHS - SXM

CHSSXM

Charleston

Thu 1/29

5:05 pm-2:10 pm

3 stops20h 05m

Simpson Bay Princess Juliana

Thu 2/5

3:20 pm-4:10 pm

3 stops25h 50m

$399

CharlestonSimpson Bay

CHS - SXM

CHSSXM

Charleston

Wed 3/4

10:20 am-1:10 pm

1 stop25h 50m

Simpson Bay Princess Juliana

Mon 3/9

3:35 pm-9:23 am

1 stop17h 48m

$476

CharlestonSimpson Bay

CHS - SXM

CHSSXM

Charleston

Fri 3/13

7:00 am-1:08 pm

1 stop6h 08m

Simpson Bay Princess Juliana

Mon 3/16

2:15 pm-11:26 pm

1 stop9h 11m

$505

CharlestonSimpson Bay

CHS - SXM

CHSSXM

Charleston

Sat 3/28

6:50 pm-11:29 am

1 stop16h 39m

Simpson Bay Princess Juliana

Sat 4/4

2:15 pm-11:26 pm

1 stop9h 11m

$523

CharlestonSimpson Bay

CHS - SXM

CHSSXM

Charleston

Sun 5/24

2:53 pm-1:16 pm

2 stops22h 23m

Simpson Bay Princess Juliana

Sat 5/30

2:11 pm-10:41 pm

1 stop8h 30m

$527

CharlestonSimpson Bay

CHS - SXM

CHSSXM

Charleston

Tue 3/3

5:00 pm-12:13 pm

2 stops18h 13m

Simpson Bay Princess Juliana

Tue 3/10

3:20 pm-11:22 am

2 stops20h 02m

$552

CharlestonSimpson Bay

CHS - SXM

CHSSXM

Charleston

Wed 3/4

5:27 am-2:50 pm

1 stop8h 23m

Simpson Bay Princess Juliana

Tue 3/10

3:20 pm-11:22 am

2 stops20h 02m

$552

CharlestonSimpson Bay

CHS - SXM

CHSSXM

Charleston

Sun 5/24

8:33 pm-1:22 pm

2 stops16h 49m

Simpson Bay Princess Juliana

Sat 5/30

4:36 pm-12:16 pm

2 stops19h 40m

$556

CharlestonSimpson Bay

CHS - SXM

CHSSXM

Charleston

Fri 5/1

11:05 am-2:05 pm

1 stop27h 00m

Simpson Bay Princess Juliana

Mon 5/4

3:10 pm-7:13 pm

1 stop28h 03m

$557

CharlestonSimpson Bay

CHS - SXM

CHSSXM

Charleston

Mon 6/1

8:33 pm-3:31 pm

2 stops18h 58m

Simpson Bay Princess Juliana

Sun 6/7

2:27 pm-10:08 am

2 stops19h 41m

$561

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/1

Compare providers for flights from Charleston 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 Charleston to Simpson Bay in January.
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 Charleston-Simpson Bay flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Charleston-Simpson Bay flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Charleston-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Charleston-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 Charleston-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 Charleston to Simpson Bay

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

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

Currently, February is the cheapest month in which you can book a flight from Charleston to Simpson Bay (average of $244). Flying from Charleston to Simpson Bay in July is currently the most expensive (average of $537). 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.

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

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 2, 2026.
Get a feel of what it's like to fly with Delta and American Airlines from Charleston to Simpson Bay by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,021 reviews

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

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
8,021 reviews
Delta
7.9
Good
8,021 reviews

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

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
11,075 reviews
Delta
7.9
Good
8,021 reviews

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

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 Charleston 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 Charleston to Simpson Bay?

    Departing from Charleston to Simpson Bay will take you 20h 05m. Airlines will cover a distance of 1467 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    American Airlines, at $506, was found to be the cheapest airline from Charleston to Simpson Bay. An alternate airline flying to your destination would be Delta. American Airlines is currently priced 23% below the average price you’ll pay for this route.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Charleston to Simpson Bay (average of $244). Flying from Charleston to Simpson Bay in July is currently the most expensive (average of $537). 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 Charleston 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 Charleston to Simpson Bay

Discover the top 2 airlines that operate flights from Charleston 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 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$506Average$642FlexibilityNo cancel feeOn-time71%
DeltaCheapest$515Average$639FlexibilityNo cancel feeOn-timeN/A

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