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St. Maarten

$250+ Cheap flights from Chesapeake, VA to St. Maarten

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.
RIC — SXM
ene. 14 — ene. 211
mié. 1/14
mié. 1/21
1 adult, Economy
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Cheap 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 diciembre 15, 2025.

This American Airlines deal was found by Cheapflights users on 12/14. 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. 12/287:37 pmORF - SXM
1 stop19h 56mAmerican Airlines
jue. 1/15:33 pmSXM - ORF
1 stop8h 26mAmerican Airlines
Deal found 12/14$988
This United Airlines deal was found by Cheapflights users on 12/14. 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.
dom. 12/286:30 amORF - SXM
2 stops30h 20mUnited Airlines
jue. 1/14:55 pmSXM - ORF
2 stops22h 15mUnited Airlines
Deal found 12/14$1,049

Find 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 diciembre 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$250
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$729
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
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($124 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 December 2025
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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 diciembre 15, 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

jue. 1/29

7:33 pm-2:10 pm

1 stop17h 37m

Simpson Bay Princess Juliana

jue. 2/5

3:15 pm-9:50 pm

2 stops31h 35m

$304

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

lun. 1/12

7:26 pm-1:45 pm

1 stop17h 19m

Simpson Bay Princess Juliana

mié. 1/21

3:31 pm-10:59 pm

1 stop8h 28m

$530

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

mié. 5/13

7:01 am-3:15 pm

1 stop8h 14m

Simpson Bay Princess Juliana

vie. 5/29

4:05 pm-11:23 pm

1 stop7h 18m

$537

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

vie. 4/24

7:01 am-3:15 pm

1 stop8h 14m

Simpson Bay Princess Juliana

vie. 5/8

2:35 pm-11:32 pm

1 stop8h 57m

$562

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

jue. 1/29

7:26 pm-3:22 pm

2 stops18h 56m

Simpson Bay Princess Juliana

jue. 2/5

5:33 pm-9:44 am

2 stops17h 11m

$567

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

vie. 12/26

2:34 pm-2:15 pm

2 stops22h 41m

$398

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

vie. 12/26

6:20 am-1:50 pm

1 stop6h 30m

$425

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

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 $237). Flying from Chesapeake to St. Maarten in June is currently the most expensive (average of $533). 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 diciembre 15, 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 42% 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 diciembre 15, 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
8,008 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

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
8,008 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

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.
United Airlines
7.4
Good
9,092 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

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
11,051 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

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.
Spirit Airlines
6.3
Okay
8,186 reviews
Delta
7.9
Good
8,008 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

7.9

Food

7.3

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 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?

    Spirit Airlines and American Airlines can get you from Chesapeake to St. Maarten in just under 17h 19m. Your travel time can differ by up to 18m. 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 $237). Flying from Chesapeake to St. Maarten in June is currently the most expensive (average of $533). 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

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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 diciembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$266Average$452FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$279Average$692FlexibilityNo cancel feeOn-time71%
DeltaCheapest$297Average$606FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$526Average$708FlexibilityNo cancel feeOn-time69%

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