C$ 159 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 24/3. 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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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

Tue, 21 Apr - Thu, 23 Apr
United Airlines Logo
2:40 p.m. - 12:33 p.m.
YOW
-
SXM
21h 53m
1 stop
United Airlines Logo
1:35 p.m. - 10:05 p.m.
SXM
-
YOW
8h 30m
1 stop
C$ 429United Airlines
Sat, 21 Feb - Sat, 14 Mar
United Airlines Logo
5:48 p.m. - 1:50 p.m.
YOW
-
SXM
19h 02m
2 stops
United Airlines Logo
1:20 p.m. - 10:26 a.m.
SXM
-
YOW
21h 06m
1 stop
C$ 448United Airlines
Sat, 25 Apr - Wed, 29 Apr
United Airlines Logo
7:43 p.m. - 12:33 p.m.
YYZ
-
SXM
16h 50m
2 stops
United Airlines Logo
3:50 p.m. - 9:54 a.m.
SXM
-
YYZ
18h 04m
2 stops
C$ 454United Airlines
Wed, 4 Mar - Wed, 11 Mar
Air Canada Logo
12:10 p.m. - 2:40 p.m.
YYZ
-
SXM
25h 30m
2 stops
Air Canada Logo
1:52 p.m. - 11:40 a.m.
SXM
-
YYZ
21h 48m
2 stops
C$ 455Air Canada
Mon, 2 Mar - Wed, 11 Mar
Air Canada Logo
8:05 p.m. - 1:50 p.m.
YYZ
-
SXM
16h 45m
1 stop
Air Canada Logo
1:52 p.m. - 11:40 a.m.
SXM
-
YYZ
21h 48m
2 stops
C$ 456Air Canada
Tue, 10 Mar - Tue, 17 Mar
WestJet Logo
5:40 a.m. - 2:17 p.m.
YOW
-
SXM
8h 37m
1 stop
WestJet Logo
3:20 p.m. - 12:39 a.m.
SXM
-
YOW
9h 19m
1 stop
C$ 458WestJet
Thu, 9 Apr - Fri, 17 Apr
WestJet Logo
5:40 a.m. - 2:17 p.m.
YOW
-
SXM
8h 37m
1 stop
WestJet Logo
3:20 p.m. - 12:39 a.m.
SXM
-
YOW
9h 19m
1 stop
C$ 462WestJet
Mon, 2 Mar - Wed, 11 Mar
American Airlines Logo
7:10 p.m. - 2:16 p.m.
YYZ
-
SXM
18h 06m
1 stop
American Airlines Logo
4:01 p.m. - 10:18 a.m.
SXM
-
YYZ
18h 17m
1 stop
C$ 463American Airlines
Wed, 11 Mar - Mon, 16 Mar
American Airlines Logo
6:00 a.m. - 1:16 p.m.
YYZ
-
SXM
7h 16m
1 stop
American Airlines Logo
4:01 p.m. - 10:18 a.m.
SXM
-
YYZ
18h 17m
1 stop
C$ 467American Airlines
Tue, 3 Mar - Tue, 10 Mar
Air Transat Logo
6:30 a.m. - 12:15 p.m.
YYZ
-
SXM
4h 45mdirect
Air Transat Logo
12:25 p.m. - 5:50 p.m.
SXM
-
YYZ
5h 25mdirect
C$ 471Air Transat
Useful Info

Good to know – Book Cheap Philipsburg Plane Tickets

Low seasonOctober
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly (3% more expensive on average)

FAQs - booking Philipsburg flights

  • How long is the flight to Philipsburg?

    Flights from Montreal4h 48m
    Flights from Toronto5h 02m
  • 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$ 227 or less one-way and C$ 570 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 509 reviews
7.9Boarding
7.0Entertainment
8.4Crew
7.3Comfort
6.8Food
Airline reviews

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.

8.0 ExcellentJanice, Feb 2026
YYZ - RIH
Read more Air Transat reviews

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.

The Turkish was good . I had a problem with air Transat terrible experience for me

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.

From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.

Very poor. The flight was delayed from Toronto because some forget to do there job . I got to my connecting gate in San Francisco 10 minutes before the departure.but this didn’t let me board even though the flight was still there for an other 30 minutes. The the gentleman at the unite airline desk told me that they usually wait for passengers but air Canada called and told them not to we I been rerouted to Manila instead of Hong Kong . In San Francisco they mad me check in my carryon bag . I was told the it will directly go yo ho chi minn cuyt but I was told that by the Vietnams airline desk that’s not there I’m 10 hours behind my scheduled flight and looks like I I’m going without baggage. I don’t have a chance of catching ..

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Reliable, nice crew, I fly often on that flight and I like it all.

l really enjoy very much the flight was very pleasant

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

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

The smell from the bathroom kept wafting through the cabin. It made people sick.

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 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.

No kiosk to help pre boarding unlike other airlines, still lost the luggage despite its own crew/TSA or security tagging it, poor handling of lost luggage and possibly compensation is likely poor too.

Waited at airport from 10 am till 4 pm and no flight due to fog. Ugh.

As someone who never flies WestJet unless there is no other viable option I have to give this crew credit where credit is due. Extremely well done everyone.

Everything was great until we had to get our bags. The bags came out in several different batches over 90 minutes after we landed maybe more we got our bags. So much for the old West Jet where they promised bags in 20 minutes. I Next time I will pack lighter and go with a carry-on.

Flight left on time. The crew was very friendly. I had to buy a proper meal. Small cookie and a drink just doesn’t cut it for a 4.5 hours flight.

The flight was full and good as could be expected. We arrived early which is always a good thing.

Experience was good, the wifi hook up is somewhat tough

Plane was one hour late. Hardly any space for our carry-ons. Stressful to catch connections.

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.

My experience was good with United too But only not so good thing was that at Calgary airport I was not given lounge access despite of flying business. Aspire lounge denied it to me, which was unfair I feel

Short flight, you can't do much. On nice days, announce the islands they're flying over.

on the longer legs, maybe a little healthy snack instead of a Celebration cookie. A second coffee would be nice. Air Canada = Second Cup. My father-in-law, Gordon White (CALPA #4) was a captain with Air Canada from age 18 to 58 on all the biggest planes. He bragged about extra treats they gave out.

The only good part was what we paid for, we travelled premium economy, good comfort travelling with a baby. Flight with AirCanada was again delayed for more than 4 hours, service level is horrible and they don't care. They deliver the bare minimum for a world class price. If you can avoid canadian air lines, do so, oligopoly does not help them to strive for any service level.

Delayed for 15 min due to maintenance. We were asked to wait to board as a family, but took longer than if we were not asked anything.

We left over 2 hours late and they didn't even give us a complimentary snack, when getting to the desk I asked if I could be put in a row with only 1 other person or an empt y one I was told the flight was full when the last two rows were empty. All around over it

there was no food or entertainment on that short 1.5 hour flight unless you mean the cookie and the overhead announcements... Those Q-400's are the workhorse of the rugged coast and mountains for sure.

they were super helpful. Agents at the desk got me on an earlier flight and I was able to get home several hours earlier.

Delayed on tarmac and missed next Air Canada flight by few minutes. Theh should have waited for me.

This is a great non-stop YVR-MIA. Very comfortable plane, and no transfer through a city that gets major winter weather!

Everything you need to know for your flight to Philipsburg