HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
St. Maarten

$364+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SXM
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chesapeake to St. Maarten with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$364
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$607
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
Highest demand for flights based on searches. 8% potential increase in price ($65 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

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 3, 2025.

This Mytrip deal was found by Cheapflights users on 4/1. 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 5/163:11 pmORF - SXM
1 stop22h 49mSpirit Airlines
Fri 5/233:05 pmSXM - ORF
1 stop23h 11mSpirit Airlines
Deal found 4/1$364
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Thu 5/153:11 pmORF - SXM
1 stop22h 49mMultiple Airlines
Sun 5/189:14 amSXM - ORF
3 stops32h 09mMultiple Airlines
Deal found 4/2$490
This Delta deal was found by Cheapflights users on 4/2. 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.
Mon 4/285:30 amORF - SXM
1 stop8h 35mDelta
Thu 5/13:30 pmSXM - ORF
1 stop8h 23mDelta
Deal found 4/2$499
This American Airlines deal was found by Cheapflights users on 4/1. 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 4/285:00 amORF - SXM
2 stops10h 24mAmerican Airlines
Thu 5/12:14 pmSXM - ORF
2 stops9h 32mAmerican Airlines
Deal found 4/1$504
This United deal was found by Cheapflights users on 4/2. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/86:00 amORF - SXM
3 stops30h 29mUnited Airlines
Wed 7/163:55 pmSXM - ORF
2 stops23h 19mUnited Airlines
Deal found 4/2$607

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 April 3, 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 5/16

3:11 pm-2:00 pm

1 stop22h 49m

Simpson Bay Princess Juliana

Fri 5/23

3:05 pm-2:16 pm

1 stop23h 11m

$364

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Thu 5/15

3:11 pm-2:00 pm

1 stop22h 49m

Simpson Bay Princess Juliana

Sun 5/18

9:14 am-5:23 pm

3 stops32h 09m

$490

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Mon 4/28

5:30 am-2:05 pm

1 stop8h 35m

Simpson Bay Princess Juliana

Thu 5/1

3:30 pm-11:53 pm

1 stop8h 23m

$499

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Mon 4/28

5:00 am-3:24 pm

2 stops10h 24m

Simpson Bay Princess Juliana

Thu 5/1

2:14 pm-11:46 pm

2 stops9h 32m

$504

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Tue 7/8

6:00 am-12:29 pm

3 stops30h 29m

Simpson Bay Princess Juliana

Wed 7/16

3:55 pm-3:14 pm

2 stops23h 19m

$607

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

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?

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 3, 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 April 3, 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
7,897 reviews

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

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
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

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
8,616 reviews
Delta
8.0
Very good
7,897 reviews

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

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
7,897 reviews

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

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
7,889 reviews
Delta
8.0
Very good
7,897 reviews

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

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

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 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

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.
Dulles Intl to Luis Munoz Marin Intl flights
Reagan-National to Luis Munoz Marin Intl flights
Dulles Intl to Punta Cana flights
Dulles Intl to Montego Bay flights
Raleigh to Luis Munoz Marin Intl flights
Dulles Intl to Saint Thomas Island flights
Dulles Intl to Oranjestad flights
Reagan-National to Montego Bay flights
Reagan-National to Punta Cana flights
Reagan-National to Nassau flights
Dulles Intl to Nassau flights
Reagan-National to Saint Thomas Island flights
Dulles Intl to Providenciales flights
Reagan-National to Oranjestad flights
Dulles Intl to Simpson Bay flights
Richmond to Luis Munoz Marin Intl flights
Dulles Intl to Castries flights
Dulles Intl to Willemstad flights
Raleigh to Saint Thomas Island flights
Reagan-National to Providenciales flights
Dulles Intl to Santo Domingo flights
Norfolk to Luis Munoz Marin Intl flights
Reagan-National to Simpson Bay flights
Dulles Intl to Bridgetown flights
Norfolk to Montego Bay flights
Raleigh to Punta Cana flights
Reagan-National to Willemstad flights
Reagan-National to Castries flights
Richmond to Montego Bay flights
Reagan-National to Bridgetown flights
Dulles Intl to Ponce flights
Raleigh to Nassau flights
Reagan-National to Kingston flights
Reagan-National to Santo Domingo flights
Dulles Intl to Kingston flights
Dulles Intl to Port of Spain flights
Reagan-National to George Town flights
Raleigh to Oranjestad flights
Richmond to Punta Cana flights
Raleigh to Montego Bay flights
Reagan-National to Christiansted flights
Reagan-National to Puerto Plata flights
Norfolk to Punta Cana flights
Reagan-National to Port of Spain flights
Dulles Intl to Christiansted flights
Dulles Intl to George Town flights
Greensboro to Luis Munoz Marin Intl flights
Raleigh to Santo Domingo flights
Greensboro to Punta Cana flights
Dulles Intl to St. John's flights

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 April 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$507FlexibilityNo cancel feeOn-time65%
DeltaCheapest$367Average$522FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$375Average$657FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$444Average$682FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.