C$ 184 Find Cheap Flights to Philipsburg

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Philipsburg departing on 28/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Cheap Flights to Philipsburg

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Philipsburg that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Philipsburg

Sat, 25 Oct - Thu, 30 Oct
United Airlines Logo
2:45 p.m. - 2:57 p.m.YYZ-SXM
24h 12m1 stop
United Airlines Logo
1:52 p.m. - 11:20 p.m.SXM-YYZ
9h 28m1 stop
C$ 465United Airlines
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Sat, 10 Jan - Wed, 14 Jan
United Airlines Logo
7:40 p.m. - 3:51 p.m.YYZ-SXM
19h 11m2 stops
United Airlines Logo
2:52 p.m. - 2:01 p.m.SXM-YYZ
24h 09m2 stops
C$ 472United Airlines
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Sat, 13 Dec - Sat, 20 Dec
American Airlines Logo
7:09 p.m. - 2:20 p.m.YYZ-SXM
18h 11m2 stops
American Airlines Logo
5:33 p.m. - 11:45 a.m.SXM-YYZ
19h 12m2 stops
C$ 478American Airlines
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Sat, 15 Nov - Wed, 19 Nov
American Airlines Logo
10:57 a.m. - 4:22 p.m.YYZ-SXM
28h 25m2 stops
American Airlines Logo
2:51 p.m. - 3:57 p.m.SXM-YYZ
26h 06m1 stop
C$ 489American Airlines
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Sat, 1 Nov - Sat, 8 Nov
Air Transat Logo
6:30 a.m. - 11:15 a.m.YYZ-SXM
4h 45mdirect
Air Transat Logo
1:25 p.m. - 5:50 p.m.SXM-YYZ
5h 25mdirect
C$ 521Air Transat
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Sat, 6 Dec - Sat, 13 Dec
Air Transat Logo
6:30 a.m. - 12:15 p.m.YYZ-SXM
4h 45mdirect
Air Transat Logo
1:25 p.m. - 5:50 p.m.SXM-YYZ
5h 25mdirect
C$ 531Air Transat
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Mon, 1 Dec - Mon, 8 Dec
WestJet Logo
9:30 a.m. - 3:21 p.m.YYZ-SXM
4h 51mdirect
WestJet Logo
4:20 p.m. - 8:43 p.m.SXM-YYZ
5h 23mdirect
C$ 535WestJet
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Fri, 2 Jan - Thu, 15 Jan
WestJet Logo
9:30 a.m. - 3:21 p.m.YYZ-SXM
4h 51mdirect
WestJet Logo
4:20 p.m. - 8:43 p.m.SXM-YYZ
5h 23mdirect
C$ 542WestJet
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Mon, 8 Dec - Fri, 12 Dec
Air Canada Logo
10:15 a.m. - 4:00 p.m.YYZ-SXM
4h 45mdirect
Air Canada Logo
5:00 p.m. - 9:15 p.m.SXM-YYZ
5h 15mdirect
C$ 545Air Canada
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Sat, 6 Dec - Sat, 13 Dec
Air Canada Logo
10:15 a.m. - 4:00 p.m.YYZ-SXM
4h 45mdirect
Air Canada Logo
3:40 p.m. - 11:40 a.m.SXM-YYZ
21h 00m2 stops
C$ 549Air Canada
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Everything you should know

Top routes
YUL-SXM
Cheapest
YYZ-SXM
Most popular
Insights
Insights
Insights
Insights
Cheapest round-trip
C$ 465
Overall average: C$ 638
United Airlines
Sat 25/10Thu 30/10
YYZ - SXM • 1 stop
Cheapest direct flights
C$ 500
Typical prices: C$ 603-C$ 970
Air Transat
Tue 3/3Tue 10/3
YYZ - SXM • Direct
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We hope you love your trip to Philipsburg!
Useful Info

Good to know – Book Cheap Philipsburg Plane Tickets

Low seasonOctober
Cheapest flightC$ 181
Best time to beat the crowds (7% less expensive on average)
Most popular time to fly and prices are also 9% lower on average.
Flight from Montreal to Simpson Bay

FAQs - booking Philipsburg flights

  • How long is the flight to Philipsburg?

    Flights from Montreal4h 47m
    Flights from Toronto5h 06m
  • What is the cheapest flight to Simpson Bay?

    In the last 3 days, the cheapest flight deal to Simpson Bay was found on the route from Montreal, at C$ 465 return. The most popular connection is from Toronto to Simpson Bay and KAYAK users have found round-trip deals for as low as C$ 465 in the last 3 days.

  • Which airlines fly to Simpson Bay?

    Many airlines fly to Simpson Bay, the most common ones being WestJet, Air Transat, and Air Canada. See the amount of flights per week for popular airlines flying to Simpson Bay.

  • How to fly to Philipsburg?

    You cannot fly directly to Philipsburg. KAYAK recommends you fly to Simpson Bay Princess Juliana (SXM) (6.75 km from Philipsburg). From there you can rent a car or get a taxi.

  • What airports are near Philipsburg?

    The closest airport is Simpson Bay Princess Juliana (SXM) (6.75 km). Other nearby airports are Gustavia St Barthelemy (SBH) (25.48 km) or Saba Island Juancho E. Yrausquin (SAB) (46.45 km). KAYAK recommends you fly to Simpson Bay Princess Juliana.

  • How far is Simpson Bay Princess Juliana Airport from central Simpson Bay?

    Central Simpson Bay is 1 km away from Simpson Bay Princess Juliana Airport.

  • What is the name of Simpson Bay’s airport?

    Simpson Bay is served by Simpson Bay Princess Juliana Airport, also commonly referred to as Princ. Juliana, Princess Juliana, Princess Juliana Intl, or St Maarten. The airport code is SXM.

  • How does KAYAK find such low prices on flights to Philipsburg?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Philipsburg.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Philipsburg?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Philipsburg is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Philipsburg?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Philipsburg with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Philipsburg?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Philipsburg up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Philipsburg

  • There is no major airport in Philipsburg. It is instead served by Simpson Bay Princess Juliana Airport.
  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 282 or less one-way and C$ 633 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Philipsburg flight deals.

Reviews of the top 5 airlines flying to Philipsburg

 
Need help choosing which airline to fly with from Canada to Philipsburg? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
Air TransatOverall score based on 466 reviews
7.9Boarding
8.5Crew
7.1Entertainment
7.4Comfort
6.8Food
Airline reviews

It was very good but no tv but the experience was great

8.0 ExcellentPatricia M, Oct 2025YUL - YEG
Read more Air Transat reviews

It was very good but no tv but the experience was great

Thank you for making my first experience very enjoyable. You made it all very pleasant

Great flight great seats will absolutely fly with you again

Porter airlines was good. I didn't have the best experience when booking through airfare assist however, as I got no final confirmation from them that the flight was booked until I called them. Even then, the confirmation code they gave me was incorrect and couldn't be used for check in. On a positive note airfare assist was actually picked up the phone relatively quickly when calling

The flight crew were very good, polite, and professional. Unfortunately, the rest of the experience left much to be desired. The food was extremely bland—almost tasteless. We chose the non vegetarian .The lasagna was just plain pasta with a tiny garnish and no seasoning. It felt like eating starch only, The bigger issue was with luggage and space. We boarded with three tickets, and while the seats in front of us were nearly empty, all the overhead compartments had already been filled by passengers boarding to the back. This left us and many others with no overhead storage for our carry-ons. Our bags couldn’t fit well under the seats either, which meant we lost the little legroom we had. The result was a horrible, cramped experience—sore knees, no space to stretch, and no way to rest or sleep comfortably. According to the crew this was a rather normal thing. It is obviously normal that people board with handbag and carry on but they should be only allowed to use their overhead compartment and under their seat not the way it is managed that all the spaces in the front of the plane being occupied by the people sitting way back in the plane.

Nice complete meal included and great services. Plus the plane was very clean.

Everything was horrible. On the day of my departure, I was denied check-in and boarding because my reservation only showed one of my last names, while my passport contains both. This minor discrepancy could have been easily corrected, but I was informed that no adjustment could be made. As a result, I lost not only my outbound flight but also my return flight and had to purchase a new ticket at a significantly higher cost.

This has been the worst experience I’ve ever had. Basically, I lost my round-trip tickets because one of my last names was missing, and you didn’t allow me to correct it. I had to purchase a full ticket again. Once I get home, I will start legal proceedings against you.

The crew were polite and courteous. The Pilot did an excellent landing. It was very smooth and gentle. My only regret is that I was charged twice for my luggage . The attendant gave me no receipt . I didn't realize until I was about to board. How can this be resolved? Thank you.

Very smooth flights Toronto to Rome and return. Crews were great, food was fine but very narrow seats and limited leg room. Aisle seats on our return helped with a bit more space.

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

The experience was great, the crew was very polite and hospitable. I will definitely make if my go to airlines.

It was all good flight was on time, service was good I enjoyed a few movies and everything was smooth

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

Very nice and clean plane. Transit time between flights was tight though

We spent too much time on board waiting for takeoff.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Good service, friendly staff. Food was average for airlines and the seats were small.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.

A cookie and a soda, packed like sardines, will never be a positive experience. Also, boarded a 5:30 flight at 7:45pm

They cancelled my flight and downgraded me to economy and only gave me $250 for the downgrade

Not very good , the stewardess were unfriendly and they don't like to be bothered. Cos was a night flight and they need to sleep.

We kept being told that the flight was full and that all overhead compartments were full and therefore had to check in our hand luggage. We were some of the last people to board and noticed that there was still sufficient space in the overhead compartments. We were obliged to check in hand luggage when there was space and so had to wait at luggage retrieval which took a while to then noticed damage to our luggage - not a great experience!

Flight delayed, missed connection, had to stay overnight. Next flight instead of our business class we were booked on the very back row. Second time this had happened in 2 months.

When I purchased the flights I included the luggage, the luggage was not added and got charged the full price anyway. Had to pay for the luggage at check in. Initial flight was delayed, we missed our 9am connection (flew with my wife), then the airline rebooks us to the next flights, putting my wife in at 1.40pm and me at 4pm, what a crazy wait time. We managed to fix it with customer service and they put me in the 1:40pm flight too, but they left my baggage behind in the 4pm flight. When arrived to my destination, of course no luggage. It was delivered to the address thankfully late at night. The experience sucked.

Very good experience. Great cabin crew. Much better than expected

There is no snack and nit much that would be considered gluten free in yiur food selections. One of your snacks should be a gluten free cookie or small bar etc. maybe it was me but I didn’t see any free movies just internet connection and YouTube .

What do you expect from a Dash 8 plane? No seats really comfortable.

Delayed 8 hours, This is the 2nd time in a month that my flight was not on time.

The snacks could have been better, and maybe some warm drinks instead of just water cause it was very very cold.

Do not fly on WestJet if you have a connection. It failed to integrate with my connecting Delta flight and I almost missed it.

The experience was good just the upcharge of over a hundred dollars was not cool.

No internet, not even westjet connect makes for a boring flight

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

Extremely turbulent landing. Crew was friendly and plane comfortable. Airport and US pre clearance was understaffed

Flight was late leaving. Charge for luggage which still has not arrived and will be delivered in a week.

More space on a sold out fight and food trays were dirty

The airplane is way too tight, you can hardly enter into your row to sit.. more like kids seats than adults.

My original flight was cancelled -- but I have to mention the excellent service I was given by the agent working at check-in who found me an earlier flight -- and helped me navigate security, ensured my baggage kept up with the quick check-in and boarding process -- and just generally made the re-booking process a breeze. Thank you! On flight was fine, but we unfortunately meant no in-flight service -- no water, or coffee (it was an early morning flight...), but the crew was pleasant and accommodating throughout.

taking our carryon and forcing us to check it through

Crew was making faces when asked for extra water. They can really use a smile while giving services. Other Than that they were good. Lots of turbulence. Also while landing it was not smooth. The tire made a loud noise. They need to make those better. Other than that everything was good.

Lovely flight.....only cold drinks and no more complimentary cookies!

Board from the back of the plane to the front - it just makes sense. Try it.

No in flight entertainment on a 750 mile flight. Made you join their "program" to get it. It was free on my first leg of the flight from Cincinnati to Toronto. In addition, there was brief period of turbulence that prohibited the crew from serving refreshments. They used that short interruption as an excuse to never serve drinks at all. They had ample time to do so and chose not to. They went around serving half cups of water instead rather than have their carts in the aisle with drinks.

Everything you need to know for your flight to Philipsburg

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