$156 Cheap Flights from Chicago (ORD) to Philipsburg (SXM)

View $156 flight on Wed, Jul 16, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM)

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Philipsburg (ORD-SXM)

Prices were available within the past 7 days and start at $156 for one-way flights and $362 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Sat, Jun 21 - Mon, Jun 23
ORD
Chicago
SXM
Saint Martin
$362 Roundtrip, found 1 day ago
$362
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Jun 21 from Chicago to Saint Martin, returning Mon, Jun 23, priced at $362 found 1 day ago
Frontier Airlines
Fri, May 30 - Fri, Jun 6
ORD
Chicago
SXM
Saint Martin
$366 Roundtrip, just found
$366
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 30 from Chicago to Saint Martin, returning Fri, Jun 6, priced at $366 just found
Frontier Airlines
Fri, Jun 6 - Fri, Jun 13
ORD
Chicago
SXM
Saint Martin
$376 Roundtrip, found 1 hour ago
$376
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Jun 6 from Chicago to Saint Martin, returning Fri, Jun 13, priced at $376 found 1 hour ago
Spirit Airlines
Mon, Jun 2 - Fri, Jun 6
ORD
Chicago
SXM
Saint Martin
$382 Roundtrip, found 1 hour ago
$382
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Mon, Jun 2 from Chicago to Saint Martin, returning Fri, Jun 6, priced at $382 found 1 hour ago
Frontier Airlines
Fri, May 30 - Sat, Jun 7
ORD
Chicago
SXM
Saint Martin
$386 Roundtrip, found 10 hours ago
$386
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Fri, May 30 from Chicago to Saint Martin, returning Sat, Jun 7, priced at $386 found 10 hours ago
Spirit Airlines
Thu, May 29 - Mon, Jun 2
ORD
Chicago
SXM
Saint Martin
$387 Roundtrip, found 4 hours ago
$387
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Thu, May 29 from Chicago to Saint Martin, returning Mon, Jun 2, priced at $387 found 4 hours ago
Frontier Airlines
Fri, May 30 - Sat, Jun 7
ORD
Chicago
SXM
Saint Martin
$393 Roundtrip, found 10 hours ago
$393
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Fri, May 30 from Chicago to Saint Martin, returning Sat, Jun 7, priced at $393 found 10 hours ago
JetBlue Airways
Sat, May 31 - Sat, Jun 7
ORD
Chicago
SXM
Saint Martin
$417 Roundtrip, found 1 hour ago
$417
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sat, May 31 from Chicago to Saint Martin, returning Sat, Jun 7, priced at $417 found 1 hour ago
American Airlines
Tue, Jul 8 - Tue, Jul 15
ORD
Chicago
SXM
Saint Martin
$622 Roundtrip, just found
$622
Roundtrip
just found
Select American Airlines flight, departing Tue, Jul 8 from Chicago to Saint Martin, returning Tue, Jul 15, priced at $622 just found
Delta
Wed, Jul 23 - Wed, Jul 30
ORD
Chicago
SXM
Saint Martin
$622 Roundtrip, found 1 hour ago
$622
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Jul 23 from Chicago to Saint Martin, returning Wed, Jul 30, priced at $622 found 1 hour ago

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM) cost?
Discover the latest flight deals from ORD to SXM by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to SXM?
The cheapest flights from ORD to SXM are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM)?
You can fly straight from O’Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM) on a United Airlines flight.
What is the cheapest airline that flies from ORD to SXM?
At the moment, the cheapest airline operating one-way flights from ORD to SXM is United. You can take off on this route from $418. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on April 26 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM)?
On average, you can take your pick of 2 direct flights taking off from O’Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM) per week. If you don’t see one that suits your schedule, think about booking a flight that has a layover. Customize your search results on Expedia to include one or two stops and choose the next best alternative.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM)?
Flights between ORD and SXM tend to be busiest at 8 AM. If you’d like a quieter experience and potentially cheaper tickets, look for a departure that’s outside typical rush times.
What day of the week has the most flights from ORD to SXM?
If you jet off on a Sunday, you’ll get the greatest range of choices for flights from O’Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM)?
The first flight of the day taking off from O’Hare Intl. Airport (ORD) is at around 8:45AM UTC-6. Board this flight and you’ll touch down at Princess Juliana Intl. Airport (SXM) at approximately 3:52PM UTC-4. The overall travel time is 5h 7m.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM)?
It takes about 5 hours and 7 minutes to travel the 2,200 mi from ORD to SXM.
What airline has the least delays from ORD to SXM?
Consider booking with United Airlines if you’d like to go straight from O’Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM) without any delays. This airline has the strongest track record for punctuality, with an on-time performance of 83%. Want to be notified if anything changes? You can check your flight status using the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM)?
To avoid possible delays on the O’Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM) route, aim to fly before 3 PM. Departures after this hour are 22% more likely to be canceled.**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 O'Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM) last-minute?
Booking your flight from ORD to SXM right before your trip is typically more expensive. But if there’s some wiggle room with your itinerary, you could land a cheap last-minute fare.
Is it cheaper to book an ORD to SXM flight and hotel package?
You can save money by booking an ORD to SXM flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it’s simple to manage it all in one place. Once you’ve chosen your preferred flights and accommodations, you can add extras such as tours, activities and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Princess Juliana Intl. Airport (SXM)?
If you booked your ORD to SXM flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of fare you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you’d like more information.
*Available to One Key members.