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Cheap Flights from Chicago O'Hare International to St Maarten

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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 to St Maarten? Find the lowest prices on one-way and return tickets right here.
Philipsburg.R 2,909 per passenger.Departing Wed, 16 Jul.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Wed, 16 Jul, arriving in St Maarten.Price includes taxes and charges.From R 2,909, select.
Philipsburg.R 3,491 per passenger.Departing Sat, 25 Oct.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 25 Oct, arriving in St Maarten.Price includes taxes and charges.From R 3,491, select.
Philipsburg.R 3,760 per passenger.Departing Sat, 10 May.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 10 May, arriving in St Maarten.Price includes taxes and charges.From R 3,760, select.
Philipsburg.R 3,814 per passenger.Departing Thu, 5 Jun.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Thu, 5 Jun, arriving in St Maarten.Price includes taxes and charges.From R 3,814, select.
Philipsburg.R 4,467 per passenger.Departing Wed, 30 Apr.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Wed, 30 Apr, arriving in St Maarten.Price includes taxes and charges.From R 4,467, select.
Philipsburg.R 4,752 per passenger.Departing Sat, 1 Nov.One-way flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 1 Nov, arriving in St Maarten.Price includes taxes and charges.From R 4,752, select.
Philipsburg.R 9,106 per passenger.Departing Sat, 1 Nov.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 1 Nov, arriving in St Maarten.Price includes taxes and charges.From R 9,106, select.
Philipsburg.R 10,634 per passenger.Departing Sat, 26 Apr.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 26 Apr, arriving in St Maarten.Price includes taxes and charges.From R 10,634, 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 July.
Apr
from R 4,467
May
from R 3,760
Jun
from R 3,814
Jul
from R 2,909
Aug
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Sep
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Oct
from R 3,491
Nov
from R 4,752
Dec
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Jan
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Feb
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Mar
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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.

Chicago to Philipsburg: Flight information

The things to know before you go.
Cheapest flight foundR 2,909
Cheapest month to flyJuly
Average flight time5 hrs, 9 mins
Most popular airlineUnited
Average flights per week2

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 R 7,536. 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 and 9 minutes is the average flight time from Chicago O'Hare International to St Maarten.
United flies direct from Chicago O'Hare International to St Maarten.
As of April 2025, there are 2 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 April 2025.
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 Monday, 2 June 2025.
Yes – the average flight time is 5 hours and 9 minutes.
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, Spirit Airlines offers the cheapest flight tickets to St Maarten.

Travelling from O'Hare International Airport (ORD) to Princess Juliana International Airport (SXM): what you need to know

  • Jump on a direct flight from O'Hare International Airport to Princess Juliana International Airport and you'll be in the air for an average of 5 hours 5 minutes.

  • To ensure you get on your ORD to SXM flight, allow plenty of time for things like baggage drop and finding your gate. Arriving two hours before international departures and one hour before domestic flights is the standard rule.

  • Taking off during a peak period like public or school holidays? Expect longer lines at check-in and security. Give yourself extra leeway and arrive up to four hours before international flights and two hours before domestic departures.

  • United Airlines has the highest passenger demand on this route.

  • United Airlines is the most punctual carrier operating ORD to SXM flights.

  • Consider adding a stopover when booking your ticket from O'Hare International Airport to Princess Juliana International Airport. Just uncheck 'Direct flights only' to break up your trip, or maybe even explore a new city along the way. Here are some options between ORD and SXM:

    • Luis Munoz Marin International Airport

    • Hartsfield-Jackson Atlanta International Airport

    • Orlando International Airport

How to find the cheapest flights from O'Hare International Airport (ORD) to Princess Juliana International Airport (SXM)

  • Currently, R 2,909 is the lowest price we've seen for a one-way O'Hare International Airport to Princess Juliana International Airport flight. The best price for a return ticket is R 7,536. Remember that fares may change due to availability at the time of booking.

  • Book ten months before flying. After crunching the numbers on our calendar, this is how far you should book ahead to secure cheap tickets from ORD to SXM.

  • Plan your trip for September. That's the cheapest month for flights from O'Hare International Airport to Princess Juliana International Airport. If you have flexibility with your dates, use the 'Whole month' tool to find the cheapest price across each month.

  • You won't have to check every day to find out if fares have gone down when you set up a Price Alert. We'll send you an update as soon as there's a change in price on cheap flights from ORD to SXM.

  • Secure the perfect flight for you by using the filters. To see the 'Fastest,' 'Cheapest' or 'Best' flights from O'Hare International Airport to Princess Juliana International Airport, use the 'Sort by' tool. You can also filter by arrival and departure times, airline, and journey duration.

Handy information about O'Hare International Airport (ORD)

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

  • When it comes to O'Hare International Airport's on-time performance, 74.85% of flights stick to their scheduled arrival time.

  • O'Hare International Airport is around 40 kilometres from central Chicago. If you're driving, ride-sharing or catching a cab from the centre, it'll take 35 minutes or so to arrive, depending on the traffic.

  • The trip on public transport typically takes 55 minutes.

  • Get your holiday off to a leisurely start by staying near ORD. Whether you're taking an early flight from O'Hare International Airport to Princess Juliana International Airport or just don't like being rushed, these hotels are the answer:

Arriving at Princess Juliana International Airport (SXM)

Getting from Princess Juliana International Airport (SXM) to central Philipsburg

  • From Princess Juliana International Airport, Philipsburg is approximately 11 kilometres away. It takes around 25 minutes to get to the centre driving.

When to fly to Princess Juliana International Airport (SXM)

  • February is the most popular month for flights from O'Hare International Airport to Princess Juliana International Airport. For smaller crowds, go to Philipsburg in April.

  • Before locking in your flight from O'Hare International Airport to Princess Juliana International Airport, consider the type of weather you enjoy. September is the warmest month in Philipsburg, with temperatures ranging from 25ºC (77ºF) to 29ºC (84ºF).

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

Plan the rest of your trip from Chicago to Philipsburg

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.