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Cheap flights from Chicago to Philipsburg

Chicago
CHI
Sint Maarten
SXM

Flight deals from Chicago to Philipsburg

Below you can see the best deals on flights Chicago — Philipsburg for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is $267.

Top 10 cheap flights from Chicago to Philipsburg

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AC
AC
$ 266

Chicago — Philipsburg

07:09—17:00
25 Jul 2026
8 h 51 m
1 stop
AC
AC
$ 304

Chicago — Philipsburg

20:40—17:00
31 Jul 2026
19 h 20 m
1 stop
F9
F9
B6
$ 380

Chicago — Philipsburg

13:50—12:37
1 Aug 2026
21 h 47 m
2 stops
F9
F9
B6
$ 387

Chicago — Philipsburg

13:50—12:37
1 Aug 2026
21 h 47 m
2 stops
F9
DL
DL
$ 391

Chicago — Philipsburg

08:05—13:55
28 Jul 2026
28 h 50 m
2 stops
F9
DL
$ 410

Chicago — Philipsburg

13:50—13:55
1 Aug 2026
23 h 5 m
1 stop
F9
DL
$ 410

Chicago — Philipsburg

07:05—13:55
1 Aug 2026
29 h 50 m
1 stop
F9
DL
$ 416

Chicago — Philipsburg

12:11—13:55
1 Aug 2026
24 h 44 m
1 stop
F9
DL
$ 416

Chicago — Philipsburg

06:05—13:55
1 Aug 2026
30 h 50 m
1 stop
AC
AC
$ 418

Chicago — Philipsburg

17:35—17:00
31 Jul 2026
22 h 25 m
1 stop
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Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Chicago — Philipsburg flight

On this page, you can find and purchase flight tickets from Chicago to Philipsburg. Flights cover a distance of 3,526 km and operate approximately 3 times a week, allowing you to choose a convenient departure time.

Flights are operated by airlines such as UA and AA. Ticket prices change constantly, so use the low-price calendar and price trend chart provided to find the best deal. You can also find information on how to get to Chicago airport and how to arrange a transfer once you arrive in Philipsburg.

Flight ticket prices by day: Chicago — Philipsburg

Below is a calendar of the lowest flight ticket prices for Chicago — Philipsburg by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $267 in n, and the most expensive are around $318 in b. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Chicago → Philipsburg, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$339highMay$269mediumSep$229low
Feb$359highJun$249lowOct$239low
Mar$359highJul$239lowNov$289medium
Apr$299mediumAug$239lowDec$329high

Some values are estimated based on seasonality.

When to fly

Climatic conditions at the destination are fairly stable; however, September is the hottest and rainiest month, with temperatures reaching 28.3°C and rainfall exceeding 200 mm. The most comfortable and dry weather for visiting the islands occurs in March and April.

According to price statistics, March is the most cost-effective month for flying, with ticket prices starting $266. October sees a seasonal increase in fares, with the minimum price starting $316.

We recommend choosing March as the optimal time for your trip — it is a great compromise between low prices and the dry season. It is advisable to avoid September due to the high probability of heavy tropical rain.

Temperature · Philipsburg

Dry and wet days · Philipsburg

Wind speed and direction · Philipsburg

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How to get the best deal on a Chicago — Philipsburg ticket

  • Book tickets with United Airlines or American Airlines 6–8 weeks before departure to secure the lowest price for this route.
  • Use the low-price calendar on this page: mid-week departures (Tuesday or Wednesday) are often cheaper than weekend flights.
  • Consider baggage allowances when comparing fares, as airport fees for a suitcase on flights from Chicago can start $64.
  • If direct flights are unavailable for your dates, consider connecting flights through major US hubs — this can save you money and offer a wider choice of departure times.

Airlines

Flights from Chicago to Philipsburg are served by 2 airlines, with United Airlines and American Airlines being the primary carriers. Direct service is not available daily, as the total number of flights is approximately 3 per week, so it is worth planning your trip in advance. Detailed information on departure times and connection options can be found in the interactive list below.

  • United AirlinesUA
    2x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → SXM2x/week
    66.7%Open →
  • American AirlinesAA
    1x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → SXM1x/week
    33.3%Open →

Cities and airports on the Chicago — Philipsburg route

Flights Chicago — Philipsburg depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Princess Juliana International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Philipsburg

SXM
Sint Maarten
About the cityHow to get thereWeatherAll about the country Sint Maarten
Departure airports
Arrival airports

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Frequently asked questions about the Chicago — Philipsburg flight

How long is the flight from Chicago to Philipsburg?

The approximate travel time for a direct flight is about 4 hours and 15 minutes, as the distance between the cities is 3,526 km.

Which airlines fly this route?

United Airlines and American Airlines operate regular flights from Chicago to Philipsburg.

Are there direct flights?

Yes, direct flights are available, but they operate with limited frequency — approximately 3 times a week.

How much is the cheapest ticket?

Flight prices change constantly depending on demand and the season. You can check current prices for your dates in the low-price calendar above on this page.

Which airport does the flight arrive at?

All flights on this route arrive at Princess Juliana International Airport (SXM), which serves Philipsburg.

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

Where else you can fly from Philipsburg

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GustaviaNew York CityBasseterreTorontoMiamiParisMontrealAtlantaWashington, D.C.CharlotteSt. John'sFort LauderdaleDominicaPhiladelphiaPanama CitySanto DomingoWillemstadPort of SpainSan JuanTortolaOrlandoAmsterdamBridgetownBostonCharlestownKingstonBradesMinneapolisCastriesKingstown

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