C$ 196 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 26/3. 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, 0 bags

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Everything you should know

Cheapest round-trip
C$ 421
Overall average: C$ 746
United Airlines
Sun 1/2Sun 8/2
YOW - SXM • 2 stops
Cheapest direct flights
C$ 440
Typical prices: C$ 528-C$ 834
WestJet
Fri 27/3Thu 2/4
YYZ - SXM • Direct
Top routes
YYZ-SXM
Cheapest
YUL-SXM
Most popular
Insights
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Flight Deals
Useful Info
Flight Deals

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

Sun, 1 Feb - Sun, 8 Feb
United Airlines Logo
7:27 p.m. - 1:50 p.m.
YOW
-
SXM
17h 23m2 stops
United Airlines Logo
4:55 p.m. - 1:32 p.m.
SXM
-
YOW
21h 37m2 stops
C$ 421United Airlines
Sun, 1 Feb - Sun, 8 Feb
United Airlines Logo
7:27 p.m. - 1:50 p.m.
YOW
-
SXM
17h 23m2 stops
United Airlines Logo
4:55 p.m. - 1:32 p.m.
SXM
-
YOW
21h 37m2 stops
C$ 422United Airlines
Fri, 27 Mar - Thu, 2 Apr
WestJet Logo
9:30 a.m. - 2:17 p.m.
YYZ
-
SXM
4h 47mdirect
WestJet Logo
3:20 p.m. - 8:42 p.m.
SXM
-
YYZ
5h 22mdirect
C$ 442WestJet
Sun, 1 Mar - Tue, 10 Mar
American Airlines Logo
7:10 p.m. - 12:29 p.m.
YYZ
-
SXM
16h 19m2 stops
American Airlines Logo
4:28 p.m. - 10:56 a.m.
SXM
-
YYZ
18h 28m2 stops
C$ 455American Airlines
Sun, 8 Mar - Thu, 12 Mar
American Airlines Logo
7:30 a.m. - 3:00 p.m.
YYZ
-
SXM
7h 30m1 stop
American Airlines Logo
4:01 p.m. - 10:17 a.m.
SXM
-
YYZ
18h 16m1 stop
C$ 458American Airlines
Fri, 23 Jan - Fri, 30 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$ 464WestJet
Mon, 19 Jan - Sun, 25 Jan
Air Canada Logo
8:30 p.m. - 2:40 p.m.
YTZ
-
SXM
17h 10m1 stop
Air Canada Logo
3:40 p.m. - 11:55 a.m.
SXM
-
YTZ
21h 15m1 stop
C$ 473Air Canada
Mon, 19 Jan - Sun, 25 Jan
Air Canada Logo
6:45 p.m. - 2:40 p.m.
YTZ
-
SXM
18h 55m2 stops
Air Canada Logo
3:40 p.m. - 11:55 a.m.
SXM
-
YTZ
21h 15m1 stop
C$ 475Air Canada
Sat, 21 Feb - Tue, 3 Mar
Multiple Airlines Logo
12:20 p.m. - 3:17 p.m.
YWG
-
SXM
24h 57m1 stop
Multiple Airlines Logo
3:20 p.m. - 3:09 p.m.
SXM
-
YWG
25h 49m2 stops
C$ 625Multiple Airlines
Mon, 23 Feb - Thu, 5 Mar
Multiple Airlines Logo
8:00 a.m. - 2:15 p.m.
YWG
-
SXM
28h 15m1 stop
Multiple Airlines Logo
3:20 p.m. - 3:09 p.m.
SXM
-
YWG
25h 49m2 stops
C$ 632Multiple Airlines
Useful Info

Good to know – Book Cheap Philipsburg Plane Tickets

Low seasonOctober
Cheapest flightC$ 196
Best time to beat the crowds (1% less expensive on average)
Flight from Toronto to Simpson Bay

FAQs - booking Philipsburg flights

  • How long is the flight to Philipsburg?

    Flights from Montreal4h 49m
    Flights from Toronto5h 03m
  • 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 Toronto, at C$ 421 return. The most popular connection is from Montreal to Simpson Bay and KAYAK users have found round-trip deals for as low as C$ 485 in the last 3 days.

  • Which airlines fly to Simpson Bay?

    Many airlines fly to Simpson Bay, the most common ones being Air Canada, WestJet, and Air Transat. 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$ 415 or less one-way and C$ 558 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.
7.7
Air TransatOverall score based on 491 reviews
7.0Entertainment
6.7Food
7.3Comfort
7.9Boarding
8.4Crew
Airline reviews

I did not like I have been charged for my carry on

6.0 GoodSilvia, Dec 2025
YUL - MCO
Read more Air Transat reviews

I did not like I have been charged for my carry on

Very good. A lot better experience then I expected for an economy flight.

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 Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Quick and seamless boarding. No entertainment but fast Starlink wifi for this short trip and the staff was really friendly.

I dread trans-Pacific flights. They are very long. This was my first time on Universal, and it was my best crossing ever. The staff were professional, the hospitality was great, and the food was delicious. The entertainment system filled the long flight hours. I will seek out Universal flights from now onwards. 🙂

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

The economy seats are very cramped and the food was bizarre. However, I did like the greek yogurt option for breakfast.

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

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.

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.

The delays were never ending and we were never properly informed as to why. 1st and 2nd delay were handled well, but by the time we received our 7th delay, and then subsequently asked to willingly get bumped, it turned into one of the worst flying situations of my life. I didn’t get home until 2am which is roughly 5 hours later than originally planned.

Great flight, great landing, nice staff. Our seats were a little cramped.

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

No food, water, snacks.”beverages”. This was on Christmas Day. Upgrading cost $100, for what exactly?

Overall good experience. The wait for baggage at our destination was quite long, but other than that everything was good as expected

Very short flight. No food or entertainment required. Nice crew. Flight left late.

My luggage was damaged 1 wheel was out I can't find it nowhere

Took 3 hours to check in and drop off our suitcases. Half of the passengers were still in line by boarding time. The computer systems and staff were very slow. Staff were also disorganized and kept allowing later flights to skip lines. Suitcases were piling on that several other passengers didn't get their suitcases. Then, we were sitting in the plane for 2 hours and were told that the flight was overbooked. We missed our connecting flight and had to fly the following day but with a stop over. Good thing ONE WestJet customer rep was pleasant and actually knew how to do her job when we wanted to rebook to a direct flight. Thank you to Kim at Toronto airport. Terrible experience at PUJ. Won't go back to Dominican Republic.

I like the wider seats, Plus lots of legroom, Lacking entertainment, no tv or screen to play with

Great seats, super comfortable, but no in flight entertainment which was a let down

My flights were all either late or canceled. It was stressful and a waste of my time. This is the third flight in a row with Air Canada that has been a scheduling mess. Not appreciated.

The airplane has been replaced and late night layover have been extended from 3 to 7 and the only compensation was a $15 food voucher after most restaurants have been closed, not helping with children after a 18+ hour international flight

Good flight. It's great you can easily go anx help yourself to snacks and water. Crew friendly and helpful. Everything ran very smoothly.

My seat was not comfortable. Flight was smooth. Regretfully we had two delays before takeoff

Amazing service, with enthusiastic crew members, and some breathtaking views of Vancouver. No IFE though, as it is only a 1 hour flight on a regional Turboprop jet.

I liked the quiet airport and no queue. I don't like that when booking it is not clear that there is teared economy, that you have to pay extra for choosing a seat and for your luggage both ways. We didn't find this out until checking in. It turned out not very economical.

No entertainment system. Paid extra for wider seats but not worth the cost. Flight left a little late and arrived early.

We boarded and then deboarded the plane after being told it needed something done that couldn't be fixed. Sent notice about 3h flight delay, then they clawed it back and we were 1h delayed. Very poor communication.

I like the fact air Canada is on time The food you guys serve is not good

Delay, after delay, after delay. It was hard as an adult travelling alone. I felt bad for the families with young children to entertain for several hours. Agents and crew performed to their usual good standard. Air Canada, never again.

Everything you need to know for your flight to Philipsburg