What are the most popular airlines that fly from Chesapeake to St. Maarten?

American Airlines, Delta and United Airlines are the most popular airlines when flying from Chesapeake to St. Maarten.

How far in advance should I book a flight from Chesapeake to St. Maarten?

To save on the cost of your flight from Chesapeake to St. Maarten, book at least 32 days before your planned departure. Booking around this time can save you about 196% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $1,024 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $1,436.

What is the cheapest month to fly from Chesapeake to St. Maarten?

The best pricing can be found in the month of September. Prices to St. Maarten from Chesapeake average $660. You can even find prices in September for less than $660, as users have found deals to St. Maarten from as low as $314. The month of December appears to be one of the more expensive times to travel to St. Maarten from Chesapeake. Flying in the targeted month can save you up to 63%.

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.

$671+ Save on Flights from Chesapeake to St. Maarten

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Cheap flight deals from Chesapeake to St. Maarten

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$518 (FlightHub)
Popular in	December
Cheapest in	September
Average price	$672

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. 9% potential increase in price ($70 potential increase over avg. RT price).

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Cheapest flight prices on average. 6% potential price decrease ($39 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in February 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 February 20, 2025.

Fri 3/148:22 pmORF - SXM

2 stops17h 06mSpirit Airlines

Fri 3/212:33 pmSXM - ORF

1 stop19h 07mSpirit Airlines

Deal found 2/20

$518

Sun 4/66:17 pmORF - SXM

2 stops18h 57mAmerican Airlines

Sun 4/134:25 pmSXM - ORF

2 stops17h 54mAmerican Airlines

Deal found 2/20

$534

Sun 4/68:00 amORF - SXM

3 stops30h 00mMultiple Airlines

Sun 4/133:55 pmSXM - ORF

2 stops25h 54mMultiple Airlines

Deal found 2/20

$612

Sat 6/76:00 amORF - SXM

1 stop8h 43mUnited Airlines

Sat 6/143:55 pmSXM - ORF

1 stop7h 50mUnited Airlines

Deal found 2/19

$781

Mon 3/176:55 amORF - SXM

1 stop7h 06mDelta

Sat 3/224:20 pmSXM - ORF

1 stop7h 43mDelta

Deal found 2/19

$892

Best flights from Chesapeake to St. Maarten
Discover carefully curated flight deals from Chesapeake to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 20, 2025.

Fri 3/148:22 pmORF - SXM

2 stops17h 06mSpirit Airlines

Fri 3/212:33 pmSXM - ORF

1 stop19h 07mSpirit Airlines

Deal found 2/19

$518

Sun 4/66:17 pmORF - SXM

2 stops18h 57mAmerican Airlines

Sun 4/134:25 pmSXM - ORF

2 stops17h 54mAmerican Airlines

Deal found 2/20

$534

Sun 4/68:00 amORF - SXM

3 stops30h 00mMultiple Airlines

Sun 4/133:55 pmSXM - ORF

2 stops25h 54mMultiple Airlines

Deal found 2/20

$612

Sat 6/76:00 amORF - SXM

1 stop8h 43mUnited Airlines

Sat 6/143:55 pmSXM - ORF

1 stop7h 50mUnited Airlines

Deal found 2/19

$781

Mon 3/176:55 amORF - SXM

1 stop7h 06mDelta

Sat 3/224:20 pmSXM - ORF

1 stop7h 43mDelta

Deal found 2/19

$892

Last-minute flights from Chesapeake to St. Maarten
Discover last-minute flight deals from Chesapeake to St. Maarten. Data last updated February 20, 2025 and is based on user searches.

Fri 3/148:22 pmORF - SXM

2 stops17h 06mSpirit Airlines

Fri 3/212:33 pmSXM - ORF

1 stop19h 07mSpirit Airlines

Deal found 2/20

$518

Fri 3/146:42 pmORF - SXM

1 stop20h 33mAmerican Airlines

Fri 3/213:20 pmSXM - ORF

1 stop8h 28mAmerican Airlines

Deal found 2/20

$660

Mon 3/176:55 amORF - SXM

1 stop7h 06mDelta

Sat 3/224:20 pmSXM - ORF

1 stop7h 43mDelta

Deal found 2/19

$892

Find flights from Chesapeake to St. Maarten within your budget

Fly from

Fly to

Route

Depart

Return

Price

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Fri 3/14

8:22 pm-1:28 pm

2 stops17h 06m

Simpson Bay Princess Juliana

Fri 3/21

2:33 pm-9:40 am

1 stop19h 07m

$518

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Sun 4/6

6:17 pm-1:14 pm

2 stops18h 57m

Simpson Bay Princess Juliana

Sun 4/13

4:25 pm-10:19 am

2 stops17h 54m

$534

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Sun 4/6

8:00 am-2:00 pm

3 stops30h 00m

Simpson Bay Princess Juliana

Sun 4/13

3:55 pm-5:49 pm

2 stops25h 54m

$612

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Sat 6/7

6:00 am-2:43 pm

1 stop8h 43m

Simpson Bay Princess Juliana

Sat 6/14

3:55 pm-11:45 pm

1 stop7h 50m

$781

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Mon 3/17

6:55 am-2:01 pm

1 stop7h 06m

Simpson Bay Princess Juliana

Sat 3/22

4:20 pm-12:03 am

1 stop7h 43m

$892

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from Chesapeake to St. Maarten

Get recent, data-driven insights about flights from Chesapeake to St. Maarten including ideal travel times, pricing trends, and more.

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 July is currently the most expensive (average of $684). 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?

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

Delta

8.0

Very good

8,219 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta

8.0

Very good

8,219 reviews

Delta

8.0

Very good

8,219 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines

7.4

Good

8,765 reviews

Delta

8.0

Very good

8,219 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

8,219 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Spirit Airlines

6.3

Okay

8,013 reviews

Delta

8.0

Very good

8,219 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

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 July is currently the most expensive (average of $684). 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

Alternative routes for Chesapeake to St. Maarten

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Greensboro to Luis Munoz Marin Intl flights

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Dulles Intl to St. John's flights

Richmond to Saint Thomas Island flights

Richmond to Nassau flights

Top 4 airlines flying from Chesapeake to St. Maarten

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$316	Average$507	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$367	Average$506	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$415	Average$634	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$444	Average$690	FlexibilityNo cancel fee	On-time69%

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$518+ 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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chesapeake to St. Maarten with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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 February 20, 2025.

Most accurate provider

Most trusted provider

Round-trip from

Popular in

Cheapest in

Average price

Find flight deals from Chesapeake to St. Maarten

Cheapest flights from Chesapeake to St. MaartenExplore 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 February 20, 2025.

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 February 20, 2025.

Find flights from Chesapeake to St. Maarten within your budget

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.

Travel insights for flights from Chesapeake to St. Maarten

Get recent, data-driven insights about flights from Chesapeake to St. Maarten including ideal travel times, pricing trends, and more.

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

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 February 20, 2025.

Reviews of airlines servicing St. Maarten

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?

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

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chesapeake to St. Maarten

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Chesapeake to St. Maarten

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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 February 20, 2025.