On this page, you can find and book flights from Philipsburg to Chicago. The 3,526 km journey is serviced regularly, with an average frequency of about 3 flights per week.
Flights on this route are operated by United Airlines and American Airlines. Ticket prices are dynamic, so use the low-price calendar to find the best deal, and be sure to check how to get to the airport and the most convenient way to reach the city upon arrival.
Below is a calendar of the lowest flight ticket prices for Philipsburg — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 1,385 in y, and the most expensive are around AED 2,204 in a. 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.
Philipsburg → Chicago, average one-way price
| Month | Average price | Level | Month | Average price | Level | Month | Average price | Level |
|---|---|---|---|---|---|---|---|---|
| Jan | AED 2,001 | high | May | AED 1,429 | low | Sep | AED 1,334 | low |
| Feb | AED 1,906 | high | Jun | AED 1,620 | medium | Oct | AED 1,284 | low |
| Mar | AED 1,855 | high | Jul | AED 1,670 | medium | Nov | AED 1,384 | low |
| Apr | AED 1,524 | low | Aug | AED 1,620 | medium | Dec | AED 1,956 | high |
Some values are estimated based on seasonality.
The most pleasant weather in Chicago is typically in July and August, when temperatures reach +26.5°C. January is the coldest month with temperatures as low as -5°C, while rainfall peaks in May and October.
According to current data, the most affordable time to fly is in December, with tickets starting AED 1,451. The most expensive period for booking at the moment is February, when the minimum price starts AED 2,204.
For a balance between price and weather, consider traveling in March, with prices starting AED 1,685. It is recommended to avoid booking for peak dates in February to ensure you don't overpay for your flight during similar weather conditions.
Two major airlines operate on this route — United Airlines and American Airlines. Together, they provide about 3 flights per week, offering both direct options and connecting flights. A detailed flight schedule and route options for each airline can be found in the interactive list below.
Flights Philipsburg — Chicago depart from Princess Juliana International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.
A direct flight on this 3,526 km route takes an average of 4 hours and 15 minutes. Travel time may increase if a connecting flight is chosen.
Regular flights between these cities are operated by the American carriers United Airlines and American Airlines.
Yes, there are direct flights on this route; however, they are infrequent—about 3 flights per week—so it is best to buy tickets in advance.
Flight prices are dynamic and depend on the season. You can check the current minimum price in the low-price calendar and the price trend chart on this page.
Flights from Sint Maarten most often arrive at O'Hare International Airport (ORD), which is the city's main aviation hub.
Where travelers fly most — pick a route and check prices
