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St. Maarten

$168+ 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 6/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SXM
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$381
(FlightHub)

One-way from

$168
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$813
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. 10% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($40 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 16, 2025.

This FlightHub deal was found by Cheapflights users on 6/15. 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 8/155:30 amORF - SXM
1 stop8h 57mSpirit Airlines
Fri 8/223:32 pmSXM - ORF
1 stop7h 17mSpirit Airlines
Deal found 6/15$381
This Mytrip deal was found by Cheapflights users on 6/16. 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 7/2510:25 amORF - SXM
2 stops27h 35mMultiple Airlines
Wed 7/303:05 pmSXM - ORF
1 stop17h 10mMultiple Airlines
Deal found 6/16$433
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Mon 10/136:51 amORF - SXM
1 stop8h 19mAmerican Airlines
Fri 10/172:40 pmSXM - ORF
1 stop8h 49mAmerican Airlines
Deal found 6/14$522
This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:30 amORF - SXM
1 stop8h 05mDelta
Mon 12/84:00 pmSXM - ORF
1 stop9h 01mDelta
Deal found 6/14$547
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Fri 7/258:10 pmORF - SXM
1 stop16h 19mUnited Airlines
Tue 7/291:35 pmSXM - ORF
1 stop10h 06mUnited Airlines
Deal found 6/16$562

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 June 16, 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

Fri 8/15

5:30 am-2:27 pm

1 stop8h 57m

Simpson Bay Princess Juliana

Fri 8/22

3:32 pm-10:49 pm

1 stop7h 17m

$381

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Fri 7/25

10:25 am-2:00 pm

2 stops27h 35m

Simpson Bay Princess Juliana

Wed 7/30

3:05 pm-8:15 am

1 stop17h 10m

$433

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Mon 10/13

6:51 am-3:10 pm

1 stop8h 19m

Simpson Bay Princess Juliana

Fri 10/17

2:40 pm-11:29 pm

1 stop8h 49m

$522

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Tue 12/2

5:30 am-2:35 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Mon 12/8

4:00 pm-12:01 am

1 stop9h 01m

$547

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Fri 7/25

8:10 pm-12:29 pm

1 stop16h 19m

Simpson Bay Princess Juliana

Tue 7/29

1:35 pm-11:41 pm

1 stop10h 06m

$562

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Sun 6/29

9:05 am-2:00 pm

1 stop28h 55m

$168

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Sun 6/29

11:34 am-2:00 pm

2 stops26h 26m

$210

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Wed 7/16

5:03 am-3:05 pm

2 stops10h 02m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

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, September is the cheapest month in which you can book a flight from Chesapeake to St. Maarten (average of $459). Flying from Chesapeake to St. Maarten in March is currently the most expensive (average of $657). 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 June 16, 2025.

When flying from Chesapeake to St. Maarten, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 June 16, 2025.
Get a feel of what it's like to fly with Delta, United Airlines and American Airlines from Chesapeake to St. Maarten by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,963 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

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
7,963 reviews
Delta
8.0
Very good
7,963 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

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
8,801 reviews
Delta
8.0
Very good
7,963 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

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
7,963 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

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
8,061 reviews
Delta
8.0
Very good
7,963 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Entertainment

7.9

Boarding

8.2

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 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.

  • 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, September is the cheapest month in which you can book a flight from Chesapeake to St. Maarten (average of $459). Flying from Chesapeake to St. Maarten in March is currently the most expensive (average of $657). 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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$367Average$553FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$375Average$662FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$400Average$507FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$444Average$703FlexibilityNo cancel feeOn-time69%

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