C$ 169 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 10/5. 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$ 396
Typical prices: C$ 735-C$ 411
Air Canada
Thu 18/6Thu 25/6
YYZ - SXM • Direct
Cheapest direct flights
C$ 393
Typical prices: C$ 750-C$ 496
WestJet
Mon 22/6Thu 2/7
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
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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

Thu, 18 Jun - Thu, 25 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$ 396Air Canada
Sun, 21 Jun - Thu, 25 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$ 399WestJet
Sun, 7 Jun - Sun, 14 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$ 400WestJet
Thu, 9 Jul - Mon, 13 Jul
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$ 403WestJet
Thu, 9 Jul - Mon, 13 Jul
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$ 404WestJet
Sun, 31 May - Thu, 4 Jun
Air Canada Logo
10:40 a.m. - 2:43 p.m.
YUL
-
SXM
28h 03m
2 stops
Air Canada Logo
6:00 p.m. - 3:24 p.m.
SXM
-
YUL
21h 24m
2 stops
C$ 470Air Canada
Fri, 29 May - Wed, 3 Jun
United Airlines Logo
5:50 p.m. - 12:33 p.m.
YOW
-
SXM
18h 43m
2 stops
United Airlines Logo
3:50 p.m. - 11:54 p.m.
SXM
-
YOW
8h 04m
1 stop
C$ 517United Airlines
Sun, 14 Jun - Thu, 18 Jun
United Airlines Logo
5:50 p.m. - 12:33 p.m.
YOW
-
SXM
18h 43m
2 stops
United Airlines Logo
3:50 p.m. - 11:54 p.m.
SXM
-
YOW
8h 04m
1 stop
C$ 554United Airlines
Wed, 27 May - Fri, 5 Jun
American Airlines Logo
4:11 p.m. - 3:42 p.m.
YQB
-
SXM
23h 31m
2 stops
American Airlines Logo
2:53 p.m. - 3:31 p.m.
SXM
-
YQB
24h 38m
2 stops
C$ 620American Airlines
Wed, 27 May - Fri, 5 Jun
American Airlines Logo
4:11 p.m. - 3:42 p.m.
YQB
-
SXM
23h 31m
2 stops
American Airlines Logo
4:43 p.m. - 1:09 p.m.
SXM
-
YQB
20h 26m
2 stops
C$ 621American Airlines
Useful Info

Good to know – Book Cheap Philipsburg Plane Tickets

Low seasonOctober
Cheapest flightC$ 169
Best time to beat the crowds but there is an average 26% increase in price.
Most popular time to fly (6% more expensive on average)
Flight from Toronto to Simpson Bay

FAQs - booking Philipsburg flights

  • How long is the flight to Philipsburg?

    Flights from Toronto4h 56m
  • 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$ 396 return. The most popular connection is from Montreal to Simpson Bay and KAYAK users have found round-trip deals for as low as C$ 470 in the last 3 days.

  • Which airlines fly to Simpson Bay?

    Many airlines fly to Simpson Bay, the most common ones being WestJet, Air Transat, and Air Canada. 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$ 250 or less one-way and C$ 577 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 537 reviews
7.1Entertainment
7.9Boarding
8.4Crew
7.3Comfort
6.8Food
Airline reviews

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.

4.0 OkayMarcel, Mar 2026
YUL - LIS
Read more Air Transat reviews

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.

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.

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

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.

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.

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.

Access to movies was rather confusing. Apart from that, I have no complaints.

I wasn’t able to book or pay for a seat and they forgot to check me in for my third flight so I spent 24 hours in Toronto waiting for another one.

I wasn’t checked in for the third leg of my flight, my bag was checked through to Dublin but when I went to the gate in Toronto they said I wasn’t on the flight and had given my seat away. I had to wait 24 hours for another flight and instead on the one I had booked it was now 2 flights.

Flight was delayed for 5hours. Food vouchers just aren’t good enough

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

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

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.

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

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.

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

Despite exit row seating, which gave leg room, seating was so narrow, the next passenger spilled over onto my seat. WiFi did not work.

It was okay. The seating didn’t give you much space especially when you book a premium. It was still pretty close. The seats had no screens which was a disappointment. The crew was awesome though. Again I wish the wait between families with children boarding and general boarding was a little longer to give families some time to get situated especially those bringing a stroller like myself or for solo parents travelling like myself who has to do everything. The time between boarding zones especially with chilling is so short, I had to gate check my stroller and did not have enough time to pull it down and transport my luggage inside all while having my infant strapped to me or to even ask a flight attendant to assist as they’re busy with the the general boarding going on

Complimentary food options could be better. There should be a little wait between people boarding with children under 6 and the rest of the boarding. There isn’t enough time to get yourself situated before take off.

Flight itself was not bad at all. However: my checked bag (checked in Calgary) did not make it onto this flight as I found out after I landed at EWR. I still don't have it but it appears that it is on its way to me.

I was tired enough to fall asleep soon after takeoff and slept until "we are starting our descent to Toronto" announcement. That's not bad at all.

Very tight seats - no legroom at all, very tight to the person in front of you. If you have basic fare, you are loading zone 6 regardless of where you are sitting in the plane - meaning even as a middle aisle person at the front of the plane, I had to get people to get up and let me in as they had boarded earlier. Having to pay for a carry on is criminal. I am a frequent flyer, and air Canada has now joined the list of other terrible North American Airlines.

The crew was amazing! I was a bit surprised and disappointed that there was not wifi available for personal use. The only thing I would change would be the seat cushions. They are not comfortable at all for long flights.

Flight and attendance were very good we had 2 hour delay that took the shine of it

Boarding went smoothly and on time. No entertainment system and only a cookie for breakfast.

This was my second leg of my trip and was delayed so was worried about my connection in Montreal. Still hungry so on boarding I asked a flight attendant if I could use my $14.00 voucher on the plane for food as I was starving. She said she would check and let me know but she never came back. So no food again as none was offered. Had to get my bags and check them again and that was ok but don’t understand why I had to go through security and because of them almost missed my flight. No food offered nor possibility to purchase food so still hungry and just watched a movie and hoped I could get food when I landed. Was able to use the $14.00 voucher to buy something and had my family bring food as I was now starving. I’ve been travelling on AC for years and this was my worst experience ever. After our flight got cancelled in SXM and was told the staff there didn’t work for AC so couldn’t do much to help us was not a good experience

Everything you need to know for your flight to Philipsburg