$90 Cheap Flights from Cleveland (CLE) to Philipsburg (SXM)

View $90 flight on Mon, Nov 17, 2025Opens in a new window

Popular airlines from Cleveland Hopkins International Airport (CLE) to Princess Juliana Intl. Airport (SXM)

Cheap Flights from Cleveland to Philipsburg (CLE-SXM)

Prices were available within the past 7 days and start at $90 for one-way flights and $335 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sat, Nov 15 - Mon, Nov 17
CLE
Cleveland
SXM
Saint Martin
$335 Roundtrip, found 5 days ago
$335
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, Nov 15 from Cleveland to Saint Martin, returning Mon, Nov 17, priced at $335 found 5 days ago
Spirit Airlines
Mon, Nov 17 - Fri, Nov 21
CLE
Cleveland
SXM
Saint Martin
$383 Roundtrip, found 1 day ago
$383
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Nov 17 from Cleveland to Saint Martin, returning Fri, Nov 21, priced at $383 found 1 day ago
Frontier Airlines
Fri, Dec 5 - Sat, Jan 10
CLE
Cleveland
SXM
Saint Martin
$391 Roundtrip, found 3 days ago
$391
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Dec 5 from Cleveland to Saint Martin, returning Sat, Jan 10, priced at $391 found 3 days ago
Spirit Airlines
Mon, Nov 17 - Fri, Nov 21
CLE
Cleveland
SXM
Saint Martin
$398 Roundtrip, found 1 day ago
$398
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Nov 17 from Cleveland to Saint Martin, returning Fri, Nov 21, priced at $398 found 1 day ago
Frontier Airlines
Fri, Dec 12 - Sat, Dec 20
CLE
Cleveland
SXM
Saint Martin
$401 Roundtrip, found 5 hours ago
$401
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Dec 12 from Cleveland to Saint Martin, returning Sat, Dec 20, priced at $401 found 5 hours ago
Frontier Airlines
Fri, Dec 12 - Sat, Dec 20
CLE
Cleveland
SXM
Saint Martin
$408 Roundtrip, found 5 hours ago
$408
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Dec 12 from Cleveland to Saint Martin, returning Sat, Dec 20, priced at $408 found 5 hours ago
Spirit Airlines
Mon, Nov 10 - Thu, Nov 27
CLE
Cleveland
SXM
Saint Martin
$422 Roundtrip, found 4 hours ago
$422
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Mon, Nov 10 from Cleveland to Saint Martin, returning Thu, Nov 27, priced at $422 found 4 hours ago
Air Canada
Fri, Nov 7 - Fri, Nov 14
CLE
Cleveland
SXM
Saint Martin
$438 Roundtrip, found 2 days ago
$438
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, Nov 7 from Cleveland to Saint Martin, returning Fri, Nov 14, priced at $438 found 2 days ago
JetBlue Airways
Sat, Jan 17 - Sat, Jan 24
CLE
Cleveland
SXM
Saint Martin
$441 Roundtrip, found 8 hours ago
$441
Roundtrip
found 8 hours ago
Select JetBlue Airways flight, departing Sat, Jan 17 from Cleveland to Saint Martin, returning Sat, Jan 24, priced at $441 found 8 hours ago
American Airlines
Wed, Apr 15 - Wed, Apr 22
CLE
Cleveland
SXM
Saint Martin
$537 Roundtrip, found 1 hour ago
$537
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Apr 15 from Cleveland to Saint Martin, returning Wed, Apr 22, priced at $537 found 1 hour ago

Find the cheapest month to fly from Cleveland (CLE) to Simpson Bay (SXM)

April is typically the cheapest month to fly

From $261 - $788 per traveler.

Alternative airports near Simpson Bay

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Clayton J. Lloyd Intl. AXA. Flights from $798
AXA
Clayton J. Lloyd Intl.
Flights from $798

Frequently asked questions

How much does a flight from Hopkins Intl. Airport (CLE) to Princess Juliana Intl. Airport (SXM) cost?
Secure a cheap one-way flight from $90 or cheap return flight from $335 from Hopkins Intl. Airport (CLE) to Princess Juliana Intl. Airport (SXM) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Hopkins Intl. Airport (CLE) to Princess Juliana Intl. Airport (SXM)?
Planning your trip for November can help you save, as it's the cheapest month for flights between CLE and SXM. You'll often find the lowest prices during off-peak months.
What is the cheapest airline that flies from Hopkins Intl. Airport (CLE) to Princess Juliana Intl. Airport (SXM)?
To find the cheapest airline flying from CLE to SXM, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Hopkins Intl. Airport (CLE) to Princess Juliana Intl. Airport (SXM)?
You'll have to book a flight with a layover when traveling from Hopkins Intl. Airport (CLE) to Princess Juliana Intl. Airport (SXM). Direct flights don't operate daily on this route. However, simply filter your search to include one or more stops to discover the best option for your trip.
What day of the week has the most flights from CLE to SXM?
You'll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Hopkins Intl. Airport (CLE) to Princess Juliana Intl. Airport (SXM)?
Choose a flight from Hopkins Intl. Airport (CLE) to Princess Juliana Intl. Airport (SXM) that leaves before 3 PM to reduce the risk of cancellations and delays. Later departures have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Hopkins Intl. Airport (CLE) to Princess Juliana Intl. Airport (SXM) last-minute?
Last-minute fares from CLE to SXM are generally more expensive. To secure the lowest rates, start searching for flights well ahead of time. That said, if you can play around with your travel dates, you may land a cheap fare right before you leave.
Is it cheaper to book a CLE to SXM flight and hotel package?
Securing a CLE to SXM flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Pick from our extensive range of accommodations and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Hopkins Intl. Airport (CLE) to Princess Juliana Intl. Airport (SXM)?
In most cases, you can reschedule or cancel your CLE to SXM flight. However, additional charges may apply, especially if your booking was made over 24 hours ago. Check your itinerary for the airline's fees and guidelines on flight changes, or if you'd like more information, go to our Customer Service portal.

Travel information

Origin airport
Hopkins Intl.
Destination airport
Princess Juliana Intl.
Airlines serving
Air Canada, American Airlines, Copa, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, United
Roundtrip price
$334
Distance
1957 mi

Book with confidence

Cleveland to Philipsburg Flights

The cheapest times to fly from Cleveland to Philipsburg

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Cleveland to Philipsburg are during the month of November. You can find some of the cheapest flights from Cleveland to Philipsburg with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Cleveland to Philipsburg

Sunday is one of the best days to book for cheap flights from Cleveland to Philipsburg: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Cleveland to Philipsburg

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Cleveland to Philipsburg in 2025. You can also book with separate airlines for your outbound and return journeys, from $90 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Cleveland to Philipsburg flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Cleveland to Philipsburg airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Cleveland to Philipsburg Flights

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*Available to One Key members.