C$ 221 Find Cheap Flights to Philipsburg – Compare and Save

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 20/8. 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$ 468
Typical prices: C$ 479-C$ 868
WestJet
Sun 18/10Thu 22/10
YYZ - SXM • Direct
Cheapest one-way flights
C$ 221
Typical prices: C$ 364-C$ 435
WestJet
Thu 20/8
YYZ - SXM • Direct
Arrival airport
You can’t fly directly to Philipsburg. It is served by Simpson Bay (SXM), located 6.7 km from Philipsburg.
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We hope you love your trip to Philipsburg!
Flight Deals
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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, 18 Oct - Thu, 22 Oct
WestJet Logo
9:30 a.m. - 2:20 p.m.
YYZ
-
SXM
4h 50mdirect
WestJet Logo
3:10 p.m. - 8:15 p.m.
SXM
-
YYZ
5h 05mdirect
C$ 468WestJet
Sun, 20 Sep - Sun, 27 Sep
WestJet Logo
9:30 a.m. - 2:20 p.m.
YYZ
-
SXM
4h 50mdirect
WestJet Logo
3:20 p.m. - 8:25 p.m.
SXM
-
YYZ
5h 05mdirect
C$ 505WestJet
Sat, 5 Sep - Sat, 12 Sep
Air Canada Logo
12:20 p.m. - 5:00 p.m.
YYZ
-
SXM
4h 40mdirect
Air Canada Logo
6:00 p.m. - 11:00 p.m.
SXM
-
YYZ
5h 00mdirect
C$ 510Air Canada
Sat, 19 Sep - Sat, 3 Oct
Air Canada Logo
12:20 p.m. - 5:00 p.m.
YYZ
-
SXM
4h 40mdirect
Air Canada Logo
6:00 p.m. - 11:00 p.m.
SXM
-
YYZ
5h 00mdirect
C$ 512Air Canada
Sat, 14 Nov - Sat, 21 Nov
United Airlines Logo
2:13 p.m. - 1:50 p.m.
YUL
-
SXM
46h 37m
2 stops
United Airlines Logo
2:10 p.m. - 3:16 p.m.
SXM
-
YUL
26h 06m
2 stops
C$ 586United Airlines
Sat, 8 Aug - Sat, 15 Aug
American Airlines Logo
7:29 a.m. - 1:42 p.m.
YUL
-
SXM
30h 13m
1 stop
American Airlines Logo
4:39 p.m. - 11:43 a.m.
SXM
-
YUL
19h 04m
2 stops
C$ 589American Airlines
Tue, 5 Jan - Fri, 15 Jan
United Airlines Logo
3:00 p.m. - 1:50 p.m.
YUL
-
SXM
21h 50m
2 stops
United Airlines Logo
2:52 p.m. - 7:38 p.m.
SXM
-
YUL
29h 46m
2 stops
C$ 596United Airlines
Sat, 15 Aug - Sat, 22 Aug
American Airlines Logo
2:30 p.m. - 1:42 p.m.
YUL
-
SXM
23h 12m
1 stop
American Airlines Logo
4:39 p.m. - 1:48 p.m.
SXM
-
YUL
21h 09m
2 stops
C$ 599American Airlines
Tue, 1 Dec - Wed, 9 Dec
Air Transat Logo
8:55 p.m. - 11:55 a.m.
YTZ
-
SXM
14h 00m
1 stop
Air Transat Logo
1:05 p.m. - 9:20 p.m.
SXM
-
YTZ
9h 15m
1 stop
C$ 709Air Transat
Tue, 24 Nov - Sat, 28 Nov
Air Transat Logo
8:55 p.m. - 11:55 a.m.
YTZ
-
SXM
14h 00m
1 stop
Air Transat Logo
1:05 p.m. - 11:10 a.m.
SXM
-
YTZ
23h 05m
1 stop
C$ 782Air Transat
Useful Info

Good to know – Book Cheap Philipsburg Plane Tickets

Low seasonSeptember
Cheapest flightC$ 221
Best time to beat the crowds (17% less expensive on average)
Most popular time to fly (7% more expensive on average)
Flight from Toronto to Simpson Bay

FAQs - booking Philipsburg flights

  • How long is the flight to Philipsburg?

    Flights from Toronto Pearson Intl Airport4h 40m
    Flights from Montreal Pierre Elliott Trudeau Intl Airport4h 35m
    Flights from Ottawa8h 41m
    Flights from Montreal4h 35m
    Flights from Toronto9h 20m
  • What is the cheapest flight to Simpson Bay?

    In the last 5 days, the cheapest flight deal to Simpson Bay was found on the route from Toronto, at C$ 468 round-trip. The most popular connection is from Montreal to Simpson Bay, while KAYAK users have found round-trip deals for as low as C$ 579 in the last 5 days.

  • 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$ 316 or less one-way and C$ 648 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 564 reviews
8.0Boarding
8.5Crew
7.1Entertainment
6.8Food
7.3Comfort
Airline reviews

Very kind crew. Vegetarian food better than usual. Prompt take off. Entertainment worked well. Could always do with more room!

10.0 ExcellentAnonymous, Jun 2026
YYZ - GLA
Read more Air Transat reviews

Very kind crew. Vegetarian food better than usual. Prompt take off. Entertainment worked well. Could always do with more room!

I liked the reliability. I liked less the chair comfort...

The dinner was bland and boring, but the economy seats were surprisingly comfortable. The flight was very packed.

I didn't have any problems during my flight. My main issue is with airlines in general, they keep offering less and less every year, AirTransat is no different.

We are a senior couple (70+) and chose emergency exit seats so we would have 2 seats together and neither of us had to sit in a middle seat. My husband is type 1 diabetic on an insulin pump and I monitor his blood sugar levels. I am 5'9" and 250 lbs and found the seats extremely uncomfortable. Toward the end of the flight I developed diarrhea which lasted a full 24 hours.

We were treated well by the staff at the airport and on board aircraft. Delay was uncontrollable due to the weather. Had to wait for another gate as we were late landing in Fort Lauderdale.

I was supose to have a carrey on incluided for each passenger and they made me paid 75$ each at the gate.

Great crew and entertaining Captain. Seats were not what we had expected based on my booking but things worked out in the end. Of course, like all airlines these days not enough leg or elbow room.

The entertainment system was down; food by purchase only; several people did not receive their luggage. No one answers at the local office or online about the luggage.

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

Friendly crew, but we were delayed for more than an hour and had to change planes due to maintenance issues.

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Boarding was smooth and efficient. The only food was some pretzels, but it was a short flight. Not much to order if you were hungry.

Crew were welcoming, accommodating and they worked hard to find places for all carry on.

Seats very comfortable; service efficient and pleasant; flight was on-time; boarding organized.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

Good but airlines getting smaller. I didn't like the meal but the service was fine. Flight was fine and luggage arrived. So good.

They were fast and I like how they used to entertainment system to play video about the safety.

Flight delayed. Connecting to night flight was stressful but made it. Jusr in time. Ran.88Flight was fine.

Our itinerary included a 1 hour and 30 minute layover, which should have been sufficient under normal circumstances. However, our original flight was delayed. Before we even deplaned, we were instructed to collect our checked bags from baggage claim, clear immigration and customs, and then recheck our bags for the connecting flight. The airline knew—or should have known—that this was impossible. Checked baggage acceptance closes one hour before departure, meaning there was no realistic way for passengers from the delayed flight to recheck their bags in time. Despite this, the airline gave us misleading instructions instead of informing us that we would likely miss our connection. We completed immigration and customs in approximately 10 minutes, but our checked bags did not arrive at the carousel for more than 30 minutes. After collecting them, we had another 10-minute walk to the baggage drop area, only to find that no airline attendant was present. We then went to another airline counter, where an employee told us this had happened before and that there was nothing they could do because the baggage acceptance window had already closed. At that point, there were still 40 minutes remaining before our flight's departure, yet no one was willing to assist or offer a practical solution. When we asked to be rebooked, we were simply told to call the airline's 800 number ourselves. There was no accountability or customer support at the airport, leaving us stranded in a foreign country with no immediate assistance. After finally reaching an agent on the 800 number, we were rebooked on a flight for the following day. However, we were initially told that the airline would not provide any hotel accommodation and that we would have to arrange and pay for it ourselves. Only after making multiple calls and speaking with several different agents did one representative finally issue a hotel voucher. The entire experience was an exhausting and frustrating ordeal. What should have been a 20-hour journey ultimately became more than 30 hours due to the airline's poor planning, misleading instructions, lack of accountability, and inadequate customer service. The unnecessary delays, confusion, and absence of meaningful assistance caused significant physical exhaustion and severe mental stress. This experience fell far below the level of service passengers should reasonably expect.

Switching flights in Halifax was a nightmare. There was no agent waiting us when we disembarked to provide my mom with gate to gate assistance as we arranged. Our flight was delayed so our window to catch the other flight was very tight. The airport was poorly marked as to where to go. The plane was fairly crowded and space available was cramped.

Good flight. We were all boarded in good time for departure time but baggage loading had barely begun. So left late. No food just snacks and basic drinks for free (food also for purchase). No entertainment as again, unable to connect with wifi on WestJet despite being a rewards member.

Average flight, comfort was as expected for a 10 hour flight. The service was fine.

Everyone was extremely friendly and nice, from the front desk to the cabin crew!

I like the idea of a non-overnight flight to Europe.

The food was very good. I was nit expecting a meal on a red eye trip. I was pleasantly surprised! Plus we arrived a few minutes earlier than expected!

The crew was excellent. The turbulence was very bad and they were unable to serve our dinner. The captain informed the passengers that we were going to get water and snack instead. They provided us ample snacks instead. Otherwise the trip was good.

Despite travelling ultra basic for the first time due to such increased rates we both managed with one bag each. Even boarding last wasn’t SO bad.

There was no food but a singular cookie for a flight that was over 5hours??? Yeah not fun I was starving and again super cramped plane and you guys need to get planes with screens too, WiFi is nice but common we need more

I got bumped by Qantas to American Airlines incurring a 6 hr layover at lax. I was not happy

Air conditioning was out for about 15 minutes that made it uncomfortable. WiFi went out halfway into the flight. Flight was about 45 minutes late.

Delayed due to weather in Dallas (arriving flight arrived late), then boarded the plane only to deboard immediately afterwards, tire needed to be replaced. Flight supposed to depart at 6:15pm but departed at 9:35pm.

Meals were not so good. Snack between the meals was very bad. Like Japan Airlines, they could eliminate the snack and make the second meal much better.

Baggage allowances are terrible and the experience of only being allowed one bag and paying so much to take sporting equipment to a known ski area should be addressed.

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

Baggage claim took too long and priority bags were not delivered first.

Horrible! Rude flight attendant, barely any service on such a long flight. I wouldn't recommend Air Canada to anyone.

I really enjoyed the delicious food and the delicious breakfast; I also liked the seat—it was very comfortable—and the service was absolutely wonderful. The trip was smooth.

The trip was very smooth; the seat was quite comfortable, and the food was excellent and tasty.

The flight from Vancouver to Victoria is a fun little hop. The crew are friendly and helpful.

The food was awful. It had more than 2 hours delay. It was too expensive

Bluetooth to use earphones with the onboard entertainment system failed. WiFi worked at least.

I was notified 8 hours before that my flight was cancelled due to mechanical issues and they would let me know when they put me on a new flight. Didn’t hear back for 6 hours and was never notified and had to log into the app to find out I was put on a new flight. First time flying with air Canada and won’t fly with them again.

They are offering less and less for more and more. They changed our seat that we paid extra to select at the last minute. The seats are way too narrow and my elbows went numb.

My original flight was canceled the day before due to mechanical issues. I had to rebook and spend $129 for a night at the airport Comfort Inn.

Overall a good experience as this leg I was in Business Class. The Lounge was amazing with a view of the planes. The flight attendant spoke way to quickly when giving the information for take off and landing and it would be of no use to a first time traveler. Overall a great airline to travel on.

Everything you need to know for your flight to Philipsburg