C$ 228 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 31/8. 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$ 471
Typical prices: C$ 609-C$ 881
WestJet
Thu 20/8Thu 27/8
YYZ - SXM • Direct
Cheapest one-way flights
C$ 228
Typical prices: C$ 366-C$ 438
WestJet
Mon 31/8
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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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

Thu, 20 Aug - Thu, 27 Aug
WestJet Logo
9:20 a.m. - 2:10 p.m.
YYZ
-
SXM
4h 50mdirect
WestJet Logo
3:10 p.m. - 8:15 p.m.
SXM
-
YYZ
5h 05mdirect
C$ 471WestJet
Thu, 20 Aug - Thu, 27 Aug
WestJet Logo
9:20 a.m. - 2:10 p.m.
YYZ
-
SXM
4h 50mdirect
WestJet Logo
3:10 p.m. - 8:15 p.m.
SXM
-
YYZ
5h 05mdirect
C$ 478WestJet
Fri, 14 Aug - Thu, 27 Aug
American Airlines Logo
7:29 a.m. - 1:33 p.m.
YUL
-
SXM
30h 04m
1 stop
American Airlines Logo
4:39 p.m. - 11:26 p.m.
SXM
-
YUL
30h 47m
1 stop
C$ 546American Airlines
Tue, 7 Jul - Fri, 10 Jul
United Airlines Logo
11:23 a.m. - 2:43 p.m.
YUL
-
SXM
27h 20m
1 stop
United Airlines Logo
3:50 p.m. - 9:26 p.m.
SXM
-
YUL
29h 36m
2 stops
C$ 548United Airlines
Wed, 8 Jul - Wed, 15 Jul
United Airlines Logo
11:00 a.m. - 2:43 p.m.
YYZ
-
SXM
27h 43m
2 stops
United Airlines Logo
3:50 p.m. - 11:54 p.m.
SXM
-
YYZ
8h 04m
1 stop
C$ 548United Airlines
Sat, 15 Aug - Tue, 25 Aug
American Airlines Logo
1:30 p.m. - 1:42 p.m.
YUL
-
SXM
24h 12m
1 stop
American Airlines Logo
4:39 p.m. - 11:43 a.m.
SXM
-
YUL
19h 04m
2 stops
C$ 562American Airlines
Thu, 29 Oct - Sat, 7 Nov
Air Canada Logo
5:45 a.m. - 1:10 p.m.
YOW
-
SXM
7h 25m
1 stop
Air Canada Logo
3:10 p.m. - 7:51 p.m.
SXM
-
YOW
29h 41m
2 stops
C$ 651Air Canada
Thu, 29 Oct - Sat, 7 Nov
Air Canada Logo
8:50 a.m. - 1:35 p.m.
YOW
-
SXM
28h 45m
2 stops
Air Canada Logo
3:10 p.m. - 7:51 p.m.
SXM
-
YOW
29h 41m
2 stops
C$ 663Air Canada
Sun, 20 Sep - Sat, 26 Sep
Multiple Airlines Logo
3:05 p.m. - 1:25 p.m.
YTZ
-
SXM
22h 20m
2 stops
Multiple Airlines Logo
12:30 p.m. - 8:57 a.m.
SXM
-
YTZ
20h 27m
2 stops
C$ 1,261Multiple Airlines
Thu, 20 Aug - Thu, 27 Aug
Multiple Airlines Logo
6:50 a.m. - 11:30 a.m.
YTZ
-
SXM
28h 40m
3 stops
Multiple Airlines Logo
11:30 a.m. - 8:57 a.m.
SXM
-
YTZ
21h 27m
2 stops
C$ 1,318Multiple Airlines
Useful Info

Good to know – Book Cheap Philipsburg Plane Tickets

Low seasonSeptember
Cheapest flightC$ 228
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 Toronto10h 52m
  • 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$ 471 return. The most popular connection is from Montreal to Simpson Bay and KAYAK users have found round-trip deals for as low as C$ 508 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$ 304 or less one-way and C$ 651 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 559 reviews
8.0Boarding
7.3Comfort
7.1Entertainment
8.5Crew
6.8Food
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

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.

Hopped on time for the flight only to get deplaned and delayed another 2.5 hours.

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 loved the fact it was on time and it was a smooth flight to my destination.

I like that we landed safely and that my dog was safe underneath as well. Outside of that, we were 45 mins late for a direct flight that is 1.5 hours long. And 2 of my 3 bags did not make the flight. Only my dog was onboard.

Service was okay except attendant over served alcohol to passenger and passenger got tipsy and made me uncomfortable

Food was not inspired but was satisfying. Same for infotainment selection. You’d think business class would come with complimentary WiFi. Crew was uniformly attentive and excellent.

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

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

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

O’Hare is a joke of a decrepit old airport. The amount of times I’ve circled that stupid place in an airplane is ridiculous. Wait in the air for a runway, wait on the tarmac for a gate…give up on O’Hare as a hub already. It can’t handle air traffic on a warm, clear, June day

check in for premium economy very nice. Friendly attendants. Best security video ever. Seriously. That's about it. Not a good bang for the premium economy buck, to be truthful. I had hoped/expected for a little more.

Delayed 2 and a half hours Middle seat next to a majorly overweight guy who took up most of my seat

The meal options were ok but the actual food was terrible. On my return journey, they simply said that there was no vegetarian option and somehow struggled to give me dinner and did not give me any breakfast at all which in my opinion was terrible. Not having ANY vegetarian meal was surprising and never had such an experience in the recent years.

Every flight was canceled and they didn’t care much about their passengers

Smooth ride but I wish they have better food selections.

Flight got delayed But satisfied with the pricing of tickets

Aircraft is designed with all 3 washrooms at the back of the plane, meaning that when there is service underway, there are no washrooms available and it gets very crowded at the back of the plane.

I was through check-in right away and on the plane before I knew it perfect in every way

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