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St. Maarten

$165+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SXM
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Wed 2/46:15 pm
ORF
-
SXM
1 stop19h 00m
Spirit Airlines
Sat 2/73:20 pm
SXM
-
ORF
1 stop28h 18m
Spirit Airlines
Deal found 1/25$322
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Wed 2/46:15 pm
ORF
-
SXM
1 stop19h 00m
Multiple Airlines
Sat 2/73:20 pm
SXM
-
ORF
2 stops20h 23m
Multiple Airlines
Deal found 1/25$344
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sat 3/148:41 pm
ORF
-
SXM
1 stop16h 27m
Spirit Airlines
Tue 3/172:14 pm
SXM
-
ORF
1 stop29h 32m
Spirit Airlines
Deal found 1/28$357
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/277:31 pm
ORF
-
SXM
1 stop17h 44m
Spirit Airlines
Mon 3/23:20 pm
SXM
-
ORF
1 stop28h 06m
Spirit Airlines
Deal found 1/27$358
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/17:31 pm
ORF
-
SXM
1 stop17h 44m
Spirit Airlines
Fri 3/63:20 pm
SXM
-
ORF
2 stops31h 30m
Spirit Airlines
Deal found 1/26$386
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/2711:32 am
ORF
-
SXM
2 stops25h 43m
Multiple Airlines
Mon 3/23:20 pm
SXM
-
ORF
1 stop28h 06m
Multiple Airlines
Deal found 1/27$387
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 3/128:41 pm
ORF
-
SXM
1 stop16h 27m
Spirit Airlines
Thu 3/192:14 pm
SXM
-
ORF
1 stop29h 32m
Spirit Airlines
Deal found 1/26$412
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 4/268:24 pm
ORF
-
SXM
1 stop16h 52m
Spirit Airlines
Sun 5/32:11 pm
SXM
-
ORF
1 stop29h 18m
Spirit Airlines
Deal found 1/26$426
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Thu 2/267:31 pm
ORF
-
SXM
1 stop17h 44m
Multiple Airlines
Sun 3/13:20 pm
SXM
-
ORF
2 stops20h 22m
Multiple Airlines
Deal found 1/28$427
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Thu 2/267:31 pm
ORF
-
SXM
1 stop17h 44m
Spirit Airlines
Sun 3/13:20 pm
SXM
-
ORF
1 stop28h 06m
Spirit Airlines
Deal found 1/28$440
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 2/267:31 pm
ORF
-
SXM
1 stop17h 44m
Spirit Airlines
Mon 3/23:20 pm
SXM
-
ORF
1 stop28h 06m
Spirit Airlines
Deal found 1/26$443

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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$357
(Kiwi.com)

One-way from

$165
(Kiwi.com)

Popular in

February

Cheapest in

September
Provider with most accurate pricing for Norfolk-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Simpson Bay Princess Juliana flights.
Search Deals
From Chesapeake to St. Maarten
Search Deals
One-way flight from Chesapeake to St. Maarten
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals

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 January 28, 2026.
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

Sat 3/14

8:41 pm-1:08 pm

1 stop16h 27m

Simpson Bay Princess Juliana

Tue 3/17

2:14 pm-7:46 pm

1 stop29h 32m

$357

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Sun 3/1

7:31 pm-2:15 pm

1 stop17h 44m

Simpson Bay Princess Juliana

Fri 3/6

3:20 pm-7:49 pm

1 stop29h 29m

$358

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Fri 2/27

11:32 am-2:15 pm

2 stops25h 43m

Simpson Bay Princess Juliana

Mon 3/2

3:20 pm-6:26 pm

1 stop28h 06m

$387

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Thu 2/26

7:31 pm-2:15 pm

1 stop17h 44m

Simpson Bay Princess Juliana

Sun 3/1

3:20 pm-10:42 am

2 stops20h 22m

$427

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Thu 2/26

7:31 pm-2:15 pm

1 stop17h 44m

Simpson Bay Princess Juliana

Sun 3/1

3:20 pm-6:26 pm

1 stop28h 06m

$440

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Thu 2/26

7:31 pm-2:15 pm

1 stop17h 44m

Simpson Bay Princess Juliana

Mon 3/2

3:20 pm-6:26 pm

1 stop28h 06m

$443

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Thu 3/12

8:41 pm-1:08 pm

1 stop16h 27m

Simpson Bay Princess Juliana

Sun 3/15

2:14 pm-7:46 pm

1 stop29h 32m

$443

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Sun 4/26

6:05 am-1:16 pm

2 stops31h 11m

Simpson Bay Princess Juliana

Sun 5/3

2:11 pm-7:29 pm

1 stop29h 18m

$473

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Thu 3/12

8:41 pm-1:08 pm

1 stop16h 27m

Simpson Bay Princess Juliana

Sun 3/15

2:14 pm-11:38 am

2 stops21h 24m

$475

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Thu 2/12

7:31 pm-2:15 pm

1 stop17h 44m

Simpson Bay Princess Juliana

Tue 2/17

3:20 pm-6:26 pm

1 stop28h 06m

$476

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 13 results
1
2

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 $527). 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.

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 January 28, 2026.
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
8,120 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

Overall

7.9

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
8,120 reviews
Delta
7.9
Good
8,120 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

Overall

7.9

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
9,206 reviews
Delta
7.9
Good
8,120 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

Overall

7.9

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
11,199 reviews
Delta
7.9
Good
8,120 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

Overall

7.9

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
8,385 reviews
Delta
7.9
Good
8,120 reviews

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Crew

8.5

Overall

7.9

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 can get you from Chesapeake to St. Maarten in just under 16h 27m. Your travel time can differ by up to . The distance from Chesapeake to St. Maarten is about 1525 mi.

  • 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 $527). 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

Browse thousands of different options on Cheapflights for your next trip

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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 5 airlines flying from Chesapeake to St. Maarten

Discover the top 5 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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$183Average$289FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$215Average$424FlexibilityNo cancel feeOn-time65%
DeltaCheapest$268Average$602FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$279Average$702FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$354Average$704FlexibilityNo cancel feeOn-time69%

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