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397 € Cheap Flights from Chicago O'Hare International to St Maarten

Compare Chicago O'Hare International to St Maarten flight deals

Find the cheapest month or even day of the year to fly to St Maarten

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Flight deals from Chicago O'Hare International to St Maarten

Looking for a cheap last-minute deal or the best return flight from Chicago O'Hare International Airport to St Maarten Airport? If you want to travel next month, return fares start from 507 €. Find the lowest prices on one-way and return tickets right here.
Philipsburg.397 € per passenger.Departing Fri, 11 Sep, returning Sat, 19 Sep.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Fri, 11 Sep, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Sat, 19 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 397 €, select.
Philipsburg.408 € per passenger.Departing Sun, 25 Oct, returning Mon, 2 Nov.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Sun, 25 Oct, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Mon, 2 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From 408 €, select.
Philipsburg.409 € per passenger.Departing Sun, 4 Oct, returning Wed, 14 Oct.Return flight with Frontier Airlines and Arajet.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sun, 4 Oct, arriving in St Maarten.Inbound indirect flight with Arajet, departs from St Maarten on Wed, 14 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 409 €, select.
Philipsburg.434 € per passenger.Departing Mon, 28 Sep, returning Sat, 3 Oct.Return flight with jetBlue and Air Canada.Outbound indirect flight with jetBlue, departs from Chicago O'Hare International on Mon, 28 Sep, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Sat, 3 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From 434 €, select.
Philipsburg.442 € per passenger.Departing Thu, 12 Nov, returning Tue, 17 Nov.Return flight with Frontier Airlines and jetBlue.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 12 Nov, arriving in St Maarten.Inbound indirect flight with jetBlue, departs from St Maarten on Tue, 17 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From 442 €, select.
Philipsburg.442 € per passenger.Departing Thu, 27 Aug, returning Sun, 6 Sep.Return flight with Frontier Airlines and Arajet.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 27 Aug, arriving in St Maarten.Inbound indirect flight with Arajet, departs from St Maarten on Sun, 6 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 442 €, select.
Philipsburg.507 € per passenger.Departing Sat, 22 Aug, returning Thu, 27 Aug.Return flight with Frontier Airlines and jetBlue.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 22 Aug, arriving in St Maarten.Inbound indirect flight with jetBlue, departs from St Maarten on Thu, 27 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 507 €, select.
Philipsburg.514 € per passenger.Departing Fri, 9 Apr, returning Thu, 15 Apr.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Fri, 9 Apr, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Thu, 15 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From 514 €, select.
Philipsburg.518 € per passenger.Departing Wed, 3 Mar, returning Sun, 7 Mar.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Wed, 3 Mar, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Sun, 7 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From 518 €, select.
Philipsburg.518 € per passenger.Departing Sat, 16 Jan, returning Sat, 23 Jan.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Sat, 16 Jan, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Sat, 23 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From 518 €, select.
Philipsburg.540 € per passenger.Departing Fri, 27 Nov, returning Fri, 4 Dec.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Fri, 27 Nov, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Fri, 4 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From 540 €, select.
Philipsburg.540 € per passenger.Departing Sat, 5 Dec, returning Sat, 12 Dec.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Sat, 5 Dec, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Sat, 12 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From 540 €, select.
Philipsburg.571 € per passenger.Departing Sat, 28 Nov, returning Sat, 5 Dec.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 28 Nov, arriving in St Maarten.Inbound direct flight with United departs from St Maarten on Sat, 5 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From 571 €, select.
Philipsburg.583 € per passenger.Departing Mon, 25 Jan, returning Mon, 1 Feb.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Mon, 25 Jan, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Mon, 1 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From 583 €, select.
Philipsburg.585 € per passenger.Departing Sat, 12 Dec, returning Sat, 19 Dec.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 12 Dec, arriving in St Maarten.Inbound direct flight with United departs from St Maarten on Sat, 19 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From 585 €, select.
Philipsburg.587 € per passenger.Departing Sat, 16 Jan, returning Sat, 23 Jan.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 16 Jan, arriving in St Maarten.Inbound direct flight with United departs from St Maarten on Sat, 23 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From 587 €, select.

Find the cheapest month to fly from Chicago O'Hare International to St Maarten

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago O'Hare International to St Maarten flights are currently cheapest in September.
Jul
Find prices
Aug
from 507 €
Sep
from 397 €
Oct
from 409 €
Nov
from 442 €
Dec
from 540 €
Jan
from 518 €
Feb
from 589 €
Mar
from 518 €
Apr
from 514 €
May
from 662 €
Jun
Find prices

Direct flights from Chicago O'Hare International to St Maarten

Chicago O'Hare International to St Maarten: Alternative routes

Compare routes from Chicago O'Hare International to Philipsburg below. You may find an airport to fly into that's cheaper, faster, or easier than St Maarten.

St Maarten

7km from central Philipsburg
ClosestCheapest
from 397 €
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Chicago to Philipsburg: Flight information

The things to know before you go.
Cheapest flight found397 €
Cheapest month to flySeptember
Average flight time5 hrs
Most popular airlineAmerican Airlines
Average flights per week3

Finding cheap flights from Chicago O'Hare International to St Maarten: Frequently asked questions

The best price we found for a return flight from Chicago O'Hare International to St Maarten is 397 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
5 hours is the average flight time from Chicago O'Hare International to St Maarten.
American Airlines and United fly direct from Chicago O'Hare International to St Maarten.
As of July 2026, there are 3 flights per week flying from Chicago O'Hare International to St Maarten.
The cheapest month to fly from Chicago O'Hare International to St Maarten is usually September.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago O'Hare International Airport to St Maarten Airport on Friday, 11 September 2026.
Yes – the average flight time is 5 hours.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to St Maarten but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Philipsburg is around 40 days in advance, so don’t leave your flight to the last minute.

Currently, Air Canada and United offer the cheapest flight tickets to St Maarten.

Flying from Chicago O'Hare International Airport (ORD) to St Maarten Airport (SXM): what you need to know

  • Take a direct flight from Chicago O'Hare International Airport to St Maarten Airport and you'll be travelling for an average of 5 hours 5 minutes.

  • Leave enough time to make your ORD to SXM flight. As a general rule, arrive two hours before international departures and an hour ahead for domestic flights.

  • Heading away during a peak time like school or public holidays? Expect longer queues at check-in and security. To play it safe, arrive up to four hours before international flights and two hours before domestic departures.

  • United tops the list for bookings on this route.

  • The most punctual carrier that operates ORD to SXM flights is United. Its services arrive without delay 66.67% of the time.

  • Think about adding a stopover when booking your ticket from Chicago O'Hare International Airport to St Maarten Airport. Just uncheck 'Direct flights only' to break up your journey, or perhaps see a new city along the way. Here's where you can stop between ORD and SXM:

    • Atlanta Hartsfield-Jackson Airport

    • Miami International Airport

    • Orlando International Airport

How to find the cheapest flights from Chicago O'Hare International Airport (ORD) to St Maarten Airport (SXM)

  • The cheapest price we've found for a one-way Chicago O'Hare International Airport to St Maarten Airport flight is 162 €. A round-trip ticket is currently 397 €. Depending on the availability and when you book, these fares may change.

  • Book four months before flying. After looking at the numbers on our calendar, this is how far you'll want to book ahead to find cheap tickets from ORD to SXM.

  • September is the cheapest month for flights from Chicago O'Hare International Airport to St Maarten Airport. If you'd like to fly at a different time of year, the 'Whole month' tool will show you the lowest airfares for each month.

  • You won't have to check every day to find out if fares have dropped when you set up a Price Alert. We'll update you the moment a special offer becomes available on cheap flights from ORD to SXM.

  • Tailor your flights using filters. Pick your preferred arrival and departure times, airlines and total journey duration. You can also sort the results by 'Best,' 'Fastest' or 'Cheapest' flights from Chicago O'Hare International Airport to St Maarten Airport.

Handy information about Chicago O'Hare International Airport (ORD)

  • You'll find ORD at 10000 West O'Hare.

  • 70% of flights that leave from Chicago O'Hare International Airport touch down at their destination on time.

  • Central Chicago to Chicago O'Hare International Airport is around 27 kilometres. Depending on traffic, it'll take you about 30 minutes to get there if you're ride-sharing, catching a taxi or driving.

  • Planning to catch public transport? Expect a journey time of around 45 minutes.

  • Get your trip off to a stress-free start by staying near ORD. Whether you're taking an early flight from Chicago O'Hare International Airport to St Maarten Airport or just don't want to be rushed, these stays are the answer:

Arriving at St Maarten Airport (SXM)

When to fly to St Maarten Airport (SXM)

  • April is the busiest month for flights from Chicago O'Hare International Airport to St Maarten Airport. To escape the crowds, travel to Philipsburg in March.

  • When booking your flight from Chicago O'Hare International Airport to St Maarten Airport, consider the type of weather you enjoy. September is the warmest month in Philipsburg, with the temperature ranging from 25ºC (77ºF) to 29ºC (84ºF).

  • February has average temperatures of between 21ºC (70ºF) and 26ºC (79ºF). Search for cheap tickets from ORD to SXM sometime around then if you'd rather travel in cooler conditions.

More travel options

Plan the rest of your trip from Chicago to Philipsburg

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.