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 $670. You can even find prices in September for less than $670, as users have found deals to St. Maarten from as low as $310. 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 72%.

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.

$544+ 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	eDreams 3 stars
Round-trip from	$503 (Delta)
Popular in	December
Cheapest in	September
Average price	$577

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. 11% potential increase in price ($85 potential increase over avg. RT price).

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Cheapest flight prices on average. 7% potential price decrease ($45 potential savings vs. average RT price).

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Average for round-trip flights in April 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 April 24, 2025.

Tue 7/87:00 amORF - SXM

1 stop6h 48mDelta

Wed 7/163:10 pmSXM - ORF

1 stop8h 56mDelta

Deal found 4/23

$503

Tue 7/85:35 amORF - SXM

2 stops9h 30mAmerican Airlines

Wed 7/164:05 pmSXM - ORF

2 stops17h 08mAmerican Airlines

Deal found 4/23

$508

Sat 11/86:00 amORF - SXM

1 stop8h 24mSpirit Airlines

Sat 11/154:27 pmSXM - ORF

2 stops27h 22mSpirit Airlines

Deal found 4/23

$538

Tue 7/88:10 pmORF - SXM

2 stops18h 33mUnited Airlines

Wed 7/163:55 pmSXM - ORF

3 stops23h 19mUnited Airlines

Deal found 4/23

$598

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 April 24, 2025.

Tue 7/87:00 amORF - SXM

1 stop6h 48mDelta

Wed 7/163:10 pmSXM - ORF

1 stop8h 56mDelta

Deal found 4/23

$503

Tue 7/85:35 amORF - SXM

2 stops9h 30mAmerican Airlines

Wed 7/164:05 pmSXM - ORF

2 stops17h 08mAmerican Airlines

Deal found 4/23

$508

Tue 9/27:44 pmORF - SXM

2 stops18h 40mSpirit Airlines

Mon 9/83:27 pmSXM - ORF

3 stops26h 35mSpirit Airlines

Deal found 4/23

$581

Tue 7/88:10 pmORF - SXM

2 stops18h 33mUnited Airlines

Wed 7/163:55 pmSXM - ORF

3 stops23h 19mUnited Airlines

Deal found 4/23

$598

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chesapeake to St. Maarten that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Tue 7/8

7:00 am-1:48 pm

1 stop6h 48m

Simpson Bay Princess Juliana

Wed 7/16

3:10 pm-12:06 am

1 stop8h 56m

$503

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Tue 7/8

5:35 am-3:05 pm

2 stops9h 30m

Simpson Bay Princess Juliana

Wed 7/16

4:05 pm-9:13 am

2 stops17h 08m

$508

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Tue 9/2

7:44 pm-2:24 pm

2 stops18h 40m

Simpson Bay Princess Juliana

Mon 9/8

3:27 pm-6:02 pm

3 stops26h 35m

$581

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Tue 7/8

8:10 pm-2:43 pm

2 stops18h 33m

Simpson Bay Princess Juliana

Wed 7/16

3:55 pm-3:14 pm

3 stops23h 19m

$598

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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 July is currently the most expensive (average of $675). 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

7,920 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

7,920 reviews

Delta

8.0

Very good

7,920 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

8,685 reviews

Delta

8.0

Very good

7,920 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

7,920 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

7,942 reviews

Delta

8.0

Very good

7,920 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 $675). 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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Raleigh to Punta Cana flights

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Dulles Intl to Ponce flights

Raleigh to Bridgetown flights

Raleigh to Montego Bay flights

Richmond to Punta Cana flights

Reagan-National to Puerto Plata flights

Reagan-National to George Town flights

Greensboro to Luis Munoz Marin Intl flights

Norfolk to Saint Thomas Island flights

Dulles Intl to St. John's flights

Raleigh to Oranjestad flights

Reagan-National to Christiansted flights

Raleigh to Simpson Bay flights

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Raleigh to Nassau flights

Dulles Intl to Santiago de los Caballeros flights

Dulles Intl to Kingston 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$522	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$375	Average$649	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$444	Average$672	FlexibilityNo cancel fee	On-time69%

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$503+ 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 7/8. 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

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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 April 24, 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 April 24, 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 April 24, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chesapeake to St. Maarten that are best for you.

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.

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?

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 April 24, 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 April 24, 2025.