C$ 199 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 20/6. 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$ 415
Typical prices: C$ 705-C$ 415
WestJet
Mon 15/6Sun 21/6
YYZ - SXM • Direct
Cheapest one-way flights
C$ 199
Typical prices: C$ 341-C$ 401
Air Canada
Sat 20/6
YUL - SXM • 1 stop
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

Mon, 15 Jun - Sun, 21 Jun
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$ 415WestJet
Sat, 13 Jun - Sat, 20 Jun
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$ 419Air Canada
Mon, 15 Jun - Sun, 21 Jun
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$ 422WestJet
Fri, 12 Jun - Sat, 20 Jun
Air Canada Logo
8:05 p.m. - 5:00 p.m.
YOW
-
SXM
20h 55m
1 stop
Air Canada Logo
6:00 p.m. - 5:15 p.m.
SXM
-
YOW
23h 15m
1 stop
C$ 448Air Canada
Mon, 8 Jun - Fri, 12 Jun
United Airlines Logo
3:10 p.m. - 2:43 p.m.
YOW
-
SXM
23h 33m
1 stop
United Airlines Logo
1:35 p.m. - 10:03 a.m.
SXM
-
YOW
20h 28m
2 stops
C$ 459United Airlines
Tue, 9 Jun - Sat, 13 Jun
United Airlines Logo
7:00 p.m. - 12:33 p.m.
YYZ
-
SXM
17h 33m
2 stops
United Airlines Logo
3:50 p.m. - 9:54 a.m.
SXM
-
YYZ
18h 04m
2 stops
C$ 459United Airlines
Sat, 22 Aug - Thu, 27 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$ 516American Airlines
Sun, 2 Aug - Sun, 9 Aug
American Airlines Logo
4:12 p.m. - 12:34 p.m.
YQB
-
SXM
20h 22m
1 stop
American Airlines Logo
4:39 p.m. - 1:12 p.m.
SXM
-
YQB
20h 33m
2 stops
C$ 647American Airlines
Sun, 6 Sep - Thu, 10 Sep
Delta Logo
6:40 a.m. - 1:53 p.m.
YWG
-
SXM
30h 13m
2 stops
Delta Logo
3:20 p.m. - 11:34 a.m.
SXM
-
YWG
21h 14m
2 stops
C$ 1,437Delta
Sun, 6 Sep - Thu, 10 Sep
Delta Logo
3:58 p.m. - 1:53 p.m.
YWG
-
SXM
20h 55m
2 stops
Delta Logo
3:20 p.m. - 8:09 p.m.
SXM
-
YWG
29h 49m
2 stops
C$ 1,439Delta
Useful Info

Good to know – Book Cheap Philipsburg Plane Tickets

Low seasonOctober
Cheapest flightC$ 199
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly (6% more expensive on average)
Flight from Montreal 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
  • 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$ 415 return. The most popular connection is from Toronto to Simpson Bay and KAYAK users have found round-trip deals for as low as C$ 415 in the last 3 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$ 219 or less one-way and C$ 552 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 553 reviews
7.9Boarding
7.3Comfort
8.5Crew
7.1Entertainment
6.8Food
Airline reviews

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

6.0 GoodJanice, May 2026
YYZ - OPO
Read more Air Transat reviews

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

Arm rests are too small and too close. No screens, movie selection was very limited and poor. Food is pretty much overpriced cheap convenience store food.

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.

Crew was good, helpful. Flight ran on time.would have liked to take airtransat home to MTL. But the price back from San Jose Costa Rica was MUCH more expensive than the flight from MTL to San Jose c.r.

i was not able to take my flight because the information i needed to book my dog correctly was not provided

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.

They never sent me a confirmation to say my flight time had changed so I cut my holiday short by 6 hours Had to pay over 50 American for my luggage to be checked on the way home and that’s more that it cost on the way there. Arbitrarily charging more for the same thing when the passenger has no options is shady The cabin was an icebox going there and back, if all the passengers have their gloves on and their hoods up that should be an obvious sign to turn up the heat

I was very nice to arrive earlier than scheduled. Very much appreciated. No issues with flight. All was good.

The on-board crew were professional and friendly and made the trip feel like we were taken care of well. The gate for the flight departure changed three times...not great but not terrible. Considering it was the day of the New Jalisco Cartel mayhem, we can't really complain.

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.

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.

Given I (and I’m assuming most people) have both carry in and a personal item included in their fare, I find it very unfair that on neither of my flights I was able to use the overhead for my small backpack because they were completely rammed with luggage, people personal items, jackets, hats and other items. So the only item I brought in had to be stuffed under my seat while they had their leg room and sat comfortable with all of their items in the overhead. This has to stop because I was uncomfortable on both flights when I only had one smaller item that could not be checked due to its contents (medication etc). Plenty of people could have checked theirs but chose not to and then took up the space allotment for 2 people.

Flight attendants had a little attitude. Food tastes no good.

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

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.

Could not make the flight. No one would help us at all

Decent entertainment although my wife was not offered any ear buds so couldn’t enjoy. Real issue was the appalling food. Presentation was unacceptable with cheap hard to open packaged bread, plastic cheese again in hard to open shrink wrap, main course in small cardboard box again hard to open, wooden utensils which lack substance making the whole experience poor. Surprised I didn’t cover myself or neighbour as the food moved all over the place. Breakfast calzone was dry and unappealing with the staff basically throwing them around. Very disappointed

Better movie options. More diligence on the size and amount of bags people bring on board. Lady across aisle from me had a bucket style bag that would only go so far under the seat in front of her. She was not told once that the whole bag is supposed to be under the seat. Crew is very hardworking however.

I didn’t have any food but my Prosecco hit the spot. We left on time and the crew was friendly.

The pricing was split into an ultra basic fare with a comfort seat upgrade. This is misleading. Never were we shown an ultra basic fare. What this did because the fare category was ultra basic we could not bid on an upgrade first class seat. All e mails from WestJet were for ultra basic category with my wife and I upset as we could not confirm this with anyone from your firm.The check in counter were not going to allow our carry on but after some checking saw we had ultra basic and a comfort seat upgrade. They could not figure out how this was done. Now we have to go through this again at the gate in Mexico. Unless I missed it - please let customers know the billing in future. Respectfully. Gary & Nancy Moughtin

Flight didn’t happen because both my connections were lost and Toronto wouldn’t let me board. I was checked in to all 3 flights at the check-in fest in Dublin.

The flight didn’t happen because they apparently lost my check in and wouldn’t let me board.

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

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.

The crew was very kind, but no in-flight entertainment monitors and a 2 hour and 30 minute delay was extremely frustrating.

American flight was diverted and delayed but app didn’t show that information so I wasn’t able to change my connection until the last min.

Flight boarded from Gate 159B, the farthest gate in the LAX Bradley Terminal. While the flight operated on time, the first class cabin attendant made no recognition of my being an Advantage Executive Platinum member.

Ceiling fell down and had to have maintenance come and duct tape it up. No WiFi on the flight.

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.

Snow delayed boarding several times, which I understand happens. Issue I had was that after we did board, pilot told us we were going to roll out to be de-iced, then on our way. We were de-iced once, taxied to the tarmac and then stopped. Sat for another 30 minutes or so, the another de-icing. Then we rolled out to a parking spot, only to sit for another hour due to a traffic stop in DCA, which I'm confident they knew would happen before we boarded. Pilot gave no updates other than we had to hold, attendants did speak to the crew, but when asked, said the pilot would be updating us. We on the ground in the plane waiting for over 2 hours. They did communicate that bathrooms would be open, but no other news until we left. Would have been better to be up front about status.

We missed our flight and got stranded in Miami where we had to rent a hotel we could not afford. they would not work with us because they said it was weather related even though the gate attendant said it was not. I could go on but trying to get satisfaction has wore me down, which I believe is the intent. My only solution is to never fly AA again.

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

The flight was smooth, the plane was spacious and clean, the staff was kind and the food was decent.

Pretzels were a bit dry and dusty, however it is nice to have a choice between sweet and savory snacks.

The pretzels were rather dry and dusty. I do appreciate having a choice between sweet and savory snack.

Staff were very friendly. Plane left on time and arrived on time.

Delays. Poor support booking a hotel after a diverted flight.

The TV screen at my seat was not functioning for the entire duration of the flight. I informed a flight attendant about the issue, and I was told that I would receive a voucher as compensation. However, I never received this voucher afterward. I therefore kindly request to still receive the voucher that was promised to me.

The staff were helpful with good relationships at all levels.- check in,in flight. BUT 1. The food provided was OK but inadequate supply. 2.in selecting my seat during the preboarding check in,I requested Change of seat which I did BUT without advice was charge $$ for this change!!

Flight crew was great, and even the crew for checking bags! I had a question for a friend of mine flying tomorrow and the man I talked to was awesome and answered my questions and looked up things for me when he didn’t have to! I was able to give her current & accurate info for her flight and she was so appreciative too!!

The Air Canada AC1 flight from Toronto to Tokyo on May 16 was great overall. Service, crew, food and entertainment were all excellent and everything ran smoothly. We had emergency exit seats so legroom was amazing, but the seats themselves weren’t very comfortable and the plane feels like it could use an upgrade for a long-haul flight. Aside from that, everything else was perfect.

Air traffic delay meant boarding started, then plane was evacuated and passengers sent back to the terminal for 1 hour. Very little information shared.

Everything you need to know for your flight to Philipsburg