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St. Maarten

$368+ Cheap flights from Chesapeake, VA to St. Maarten

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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SXM
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Chesapeake to St. Maarten

Keep the following information in mind while searching for Chesapeake to St. Maarten flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$440
(Kiwi.com)

One-way from

$368
(United Airlines)

Popular in

June

Cheapest in

September

Average price

$537
Provider with most accurate pricing for Norfolk-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Simpson Bay Princess Juliana flights.
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From Chesapeake to St. Maarten
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One-way flight from Chesapeake to St. Maarten
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Highest demand for flights based on searches. 16% potential increase in price ($128 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 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 Chesapeake to St. Maarten

Cheapest flights from Chesapeake to St. Maarten
Explore the most affordable flight options available from Chesapeake to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:11 pmORF - SXM
1 stop17h 04mSpirit Airlines
Fri 12/193:20 pmSXM - ORF
1 stop30h 10mSpirit Airlines
Deal found 10/28$440
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/148:11 pmORF - SXM
1 stop17h 04mMultiple Airlines
Sun 12/211:45 pmSXM - ORF
2 stops25h 21mMultiple Airlines
Deal found 10/30$445
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:05 amORF - SXM
1 stop8h 52mUnited Airlines
Sun 12/215:00 pmSXM - ORF
1 stop7h 41mUnited Airlines
Deal found 10/30$562
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:05 amORF - SXM
1 stop8h 52mUnited Airlines
Sat 12/205:00 pmSXM - ORF
1 stop7h 41mUnited Airlines
Deal found 10/29$697
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.
Fri 12/128:38 amORF - SXM
2 stops29h 02mMultiple Airlines
Fri 12/195:00 pmSXM - ORF
3 stops26h 45mMultiple Airlines
Deal found 10/28$849

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to St. Maarten 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 Chesapeake to St. Maarten that are best for you.

Fly from

Chesapeake

Fly to

St. Maarten

Route

Depart

Return

Price

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Sun 12/14

8:11 pm-2:15 pm

1 stop17h 04m

Simpson Bay Princess Juliana

Sun 12/21

1:45 pm-2:06 pm

2 stops25h 21m

$445

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Tue 3/10

6:00 am-2:51 pm

1 stop8h 51m

Simpson Bay Princess Juliana

Tue 3/17

3:55 pm-11:38 pm

1 stop7h 43m

$537

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Fri 12/12

8:11 pm-2:15 pm

1 stop17h 04m

Simpson Bay Princess Juliana

Fri 12/19

3:20 pm-6:45 pm

3 stops28h 25m

$561

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Tue 1/6

6:10 am-2:31 pm

1 stop7h 21m

Simpson Bay Princess Juliana

Fri 1/9

2:03 pm-11:29 pm

1 stop10h 26m

$561

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Sun 12/14

6:05 am-3:57 pm

1 stop8h 52m

Simpson Bay Princess Juliana

Sun 12/21

5:00 pm-11:41 pm

1 stop7h 41m

$562

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Wed 11/12

6:04 am-1:50 pm

1 stop6h 46m

$405

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Wed 11/19

8:05 pm-1:50 pm

2 stops16h 45m

$411

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Fri 12/26

10:46 am-1:50 pm

1 stop26h 04m

$1,064

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Fri 12/26

10:46 am-4:00 pm

2 stops28h 14m

$3,960

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Best time to book a flight from Chesapeake to St. Maarten

Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Chesapeake 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 Chesapeake to St. Maarten

What is the cheapest month to book a flight from Chesapeake to St. Maarten?

Currently, November is the cheapest month in which you can book a flight from Chesapeake to St. Maarten (average of $245). Flying from Chesapeake to St. Maarten in February is currently the most expensive (average of $549). 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.

What is the cheapest time of day to fly from C6E to SX?

Find hourly flight availability from Chesapeake to St. Maarten. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

One of the essential ways to save on airfare from Chesapeake to St. Maarten is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 34% on airfare.

Reviews of airlines servicing St. Maarten

Get insights into the airlines that provide service to St. Maarten. 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 St. Maarten. Reviews last updated October 30, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Chesapeake to St. Maarten. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

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
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

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.
United Airlines
7.4
Good
8,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

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
11,035 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

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.
Spirit Airlines
6.3
Okay
8,116 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.2

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 Chesapeake to St. Maarten. 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 Chesapeake to St. Maarten?

    United Airlines, Spirit Airlines, and American Airlines can get you from Chesapeake to St. Maarten in just under 7h 21m. Your travel time can differ by up to 9h 43m. The distance from Chesapeake to St. Maarten is about 1525 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Chesapeake to St. Maarten that include hotel bookings?

    Yes. In addition to deals on Chesapeake to St. Maarten flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to St. Maarten?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to St. Maarten.

  • Can I find deals for business class flights from Chesapeake to St. Maarten?

    Yes. Cheapflights offers flight deals from Chesapeake to St. Maarten 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 Chesapeake to St. Maarten?

    Currently, November is the cheapest month in which you can book a flight from Chesapeake to St. Maarten (average of $245). Flying from Chesapeake to St. Maarten in February is currently the most expensive (average of $549). 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 Chesapeake to St. Maarten

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chesapeake to St. Maarten

Discover the top 4 airlines that operate flights from Chesapeake to St. Maarten. 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
Spirit AirlinesCheapest$266Average$452FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$279Average$691FlexibilityNo cancel feeOn-time71%
DeltaCheapest$457Average$594FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$465Average$711FlexibilityNo cancel feeOn-time69%

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