C$ 144 Find Cheap Flights to Philipsburg – Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Useful Info
Flight Deals

Cheap Flights to Philipsburg

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Philipsburg

Sat, 20 Feb - Sat, 6 Mar
WestJet Logo
6:35 a.m. - 12:30 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mdirect
WestJet Logo
1:30 p.m. - 5:55 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mdirect
C$ 386WestJet
Sun, 22 Nov - Sat, 28 Nov
WestJet Logo
9:30 a.m. - 3:25 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mdirect
WestJet Logo
1:30 p.m. - 5:55 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mdirect
C$ 388WestJet
Wed, 13 Jan - Sun, 17 Jan
Air Canada Logo
9:50 a.m. - 3:45 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mdirect
Air Canada Logo
4:45 p.m. - 9:05 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 20mdirect
C$ 400Air Canada
Mon, 18 Jan - Tue, 2 Mar
Air Canada Logo
9:50 a.m. - 3:45 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 55mdirect
Air Canada Logo
4:40 p.m. - 8:55 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 15mdirect
C$ 400Air Canada
Sat, 24 Oct - Sat, 31 Oct
Multiple Airlines Logo
12:20 p.m. - 5:00 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 40mdirect
Multiple Airlines Logo
1:30 p.m. - 6:55 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mdirect
C$ 406Multiple Airlines
Sat, 16 Jan - Sat, 23 Jan
Air Transat Logo
6:30 a.m. - 12:15 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 45mdirect
Air Transat Logo
1:25 p.m. - 5:50 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mdirect
C$ 407Air Transat
Sat, 24 Oct - Sat, 31 Oct
Multiple Airlines Logo
12:20 p.m. - 5:00 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
4h 40mdirect
Multiple Airlines Logo
1:30 p.m. - 6:55 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mdirect
C$ 407Multiple Airlines
Fri, 11 Dec - Fri, 25 Dec
United Airlines Logo
6:10 a.m. - 3:57 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
32h 47m2 stops Houston George Bush Intcntl Chicago O'Hare Intl
United Airlines Logo
2:10 p.m. - 11:59 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
10h 49m1 stop Chicago O'Hare Intl
C$ 436United Airlines
Fri, 11 Dec - Fri, 25 Dec
United Airlines Logo
7:26 p.m. - 3:57 p.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
19h 31m1 stop Chicago O'Hare Intl
United Airlines Logo
2:52 p.m. - 11:26 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
9h 34m1 stop Newark
C$ 436United Airlines
Tue, 2 Feb - Sat, 6 Mar
Air Transat Logo
8:55 p.m. - 11:55 a.m.YYZ  Toronto Pearson Intl-SXM Simpson Bay Princess Juliana
14h 00m1 stop Montreal Pierre Elliott Trudeau Intl
Air Transat Logo
1:25 p.m. - 5:50 p.m.SXM  Simpson Bay Princess Juliana-YYZ Toronto Pearson Intl
5h 25mdirect
C$ 450Air Transat
Useful Info

Good to know – Book Cheap Philipsburg Plane Tickets

Low season

September

Cheapest flight

C$ 144
Best time to beat the crowds (14% less expensive on average)
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 Toronto Pearson Intl Airport4h 40m
    Flights from Montreal Pierre Elliott Trudeau Intl Airport4h 35m
    Flights from Ottawa7h 25m
    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$ 386 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$ 461 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$ 187 or less one-way and C$ 472 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 575 reviews
7.3Comfort
8.0Boarding
7.1Entertainment
8.5Crew
6.8Food
Airline reviews

Flight was really good, with no middle section on an A321neo for an international flight, from Ottawa directly to London. Staff was friendly. The food was okay, and entertainment amenities could be better.

10.0 ExcellentTony, Aug 2026
Read more Air Transat reviews

Flight was really good, with no middle section on an A321neo for an international flight, from Ottawa directly to London. Staff was friendly. The food was okay, and entertainment amenities could be better.

The flight was terrible based off the temperature in the plane and the air smelled so stale and gross. I have never wanted to hosed lore in my life after I got off. The food was disgusting and seemingly low quality. The staff was friendly. The bathrooms were so gross after a couple of hours. I will definitely never book with them again.

The crew was great. There was no entertainment and the internet wasn't working. We sat in the run way for a LONG time which is always so upsetting. The seats are very close together and the flights are completely full which makes for a tough flight. Flying is just an uncomfortable experience.

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.

The website check in was poor. Baggage fees were in US dollars but registered in Canadian dollars. The site would not accept my credit card. Scanning the passport was the worst. Someone from United needs to try the process. I’m not a novice with tech and I have to say this was a bad experience. Everything else was great.

We boarded the plane and were about to take off when we were notified that the tires had to be checked. Upon inspection, they were found to need replacement, so the entire plane had to be deboarded. After we exited the plane, United staff forced us to stay in the gate area by posting "Do Not Exit" signs on the doors connecting the gate area to the terminal. Many of us had already rebooked our flights and had no checked bags, but they told us we could not leave. This seemed inappropriate to hold people under false pretenses. When the agent told us we could leave, I asked them to please take down the "Do Not Exit" signs, as they were misleading. The agent refused, and I told them that it didn't feel right to hold people like that.

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.

I think I'd sum up my experiences on this flight (Edinburgh to Toronto) by saying that Boeing 737s are simply too small for long-haul, transatlantic flights. The crew were excellent, the food was pretty good and the in-flight Wifi was a bonus. But 7+ hours on a narrow bodied aircraft with a single aisle and no in-built entertainment system, is a tough stretch - queues for the few toilets on board were lengthy at times; plus whilst the crew were doing food/drink service the aisle is blocked. It encourages you to stay in your seat the entire time (not great for those who need to get up and move around regularly) and the legroom is tight anyway. If this was priced as uber-budget, you could perhaps argue that you're getting what you paid for......but it wasn't and the price we paid was pretty standard for such trips (around £500 pp). I'd therefore urge caution and check the aircraft that is being used if booking with Westjet for flights to Canada from smaller regional airports on the Western edge of Europe. They do operate Boeing 787s from London and other major European centres - but it seems that if travelling from Scotland/Ireland the 737 is the aircraft of choice.......

Terrible. I was charged $75 for a checked bag when I only had a carry on. The lady at the desk said she couldn’t refund me the money and that I had to call westjet. I called the next day and they said they couldn’t refund me because there is no way to prove I didn’t have a checked bag.

I'm so frustrated my flight was canceled they give flight on August 5 which is not sure. Its was big mistake I booked my ticket from kayak.

Maybe glass of wine would be nice at no charge

We traveled with a 7 year old that has autism and he is significantly cognitively delayed. Your site makes it known there are no wagons allowed even if they fold down flat and many autistic children cannot travel without one because they are unable to follow directions or cooperate with walking through the airport and are too big for a stroller. Please consider making exceptions for our special needs children. Also it would be very thoughtful if you’d allow seat selection for no fee for special needs families. The autistic child we traveled with must sit behind another adult in our family because he continuously kicks the seat in front of him and is unable to understand why that is disruptive. We had to pay quite a bit extra to have our 4 seats situated with 2 in row 19 and 2 in row 20 directly behind.

It would have been nice to know there was no on flight entertainment

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.

This may have been the hottest cabin temperatures I have experienced on any flight prior to take off lasting for approximately 30 minutes. I am not typically one to complain but I was genuinely worried about the health of several passengers on the flight due to the extreme temperatures including a small toddler.

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.

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

Original flight was canceled by Air Canada and next day they re scheduled and paid by hotel and taxi cost, but it just so tired for waiting and I have some school exam that I couldn't prepare it at all.

Packed very carefully and did a 4 day trip with a 'personal item' only. Much less trouble than a carry on. Only 'entertainment' i need is the flight map. Did not work.

Our family of four were seated separated entirely from one another. We were hopeful to at least be paired up with our children in groups of two. Remember that no food is provided. You will get two beverages and a single Made Good granola bite size bar. Air Canada Bistro menu is available for purchase. Blankets, pillows, and headphones are also available for purchase.

Liked that it wasnt a full flight but we were asked to check carry on luggage as we were told the flight was full so i did, and that was not true. There was tons of empty overhead bins. No entertainment, and only one drinks and snack service when my ladt flight on aircanada in February, Montréal to Victoria had 2 drink service offers in the 5 and a half hour flight. Why only one this time? It felt very "budget" and cheap

Flight attendants are great. Seat was fairly comfortable. WiFi is for a fee unless you happen to enter an Air Canada member number *when booking*. Cannot change this in flight. Vegetarian food was tasty but lacked protein of any kind.

Advertised as free carry on bag for international flights and then I had to pay both ways.

Delayed as usual with Air Canada. Checked the status of the fly online it said took off when the plain was still at the gate.

Not great. Missed my connection flight, due to AC issue. We were sitting on the tarmac for 90 mins before taking off.

The flight from Anchorage to Vancouver was OK, but the seats are quite uncomfortable.

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