Cheap Flights from St Maarten to Chicago O'Hare International

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Flight deals from St Maarten to Chicago O'Hare International

Looking for a cheap last-minute deal or the best return flight from St Maarten to Chicago O'Hare International? Find the lowest prices on one-way and return tickets right here.

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

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like St Maarten to Chicago O'Hare International flights are currently cheapest in February.

Direct flights from St Maarten to Chicago O'Hare International

St Maarten to Chicago O'Hare International: Alternative routes

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

Philipsburg to Chicago: Flight information

The things to know before you go.
Cheapest flight found$368
Cheapest month to flyFebruary
Average flight time5 hrs, 53 mins
Most popular airlineAmerican Airlines
Average flights per week3

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

The best price we found for a return flight from St Maarten to Chicago O'Hare International is $368. 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 53 minutes is the average flight time from St Maarten to Chicago O'Hare International.
American Airlines and United fly direct from St Maarten to Chicago O'Hare International.
As of February 2026, there are 3 flights per week flying from St Maarten to Chicago O'Hare International.
The cheapest month to fly from St Maarten to Chicago O'Hare International is usually February.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from St Maarten Airport to Chicago O'Hare International Airport on Friday, 27 February 2026.
Yes – the average flight time is 5 hours and 53 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 Chicago O'Hare International 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Spirit Airlines and United offer the cheapest flight tickets to Chicago O'Hare International.

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

  • Chicago is one hour behind Philipsburg and is in the UTC-5 timezone.

  • To ensure you catch your SXM to ORD flight, allow plenty of time to check in and drop off your luggage. Turning up two hours before international departures and an hour before domestic flights is the general rule.

  • Flying during a peak month like February? Public holidays and other popular seasons can result in longer lines at airport checkpoints. Play things extra safe and arrive up to four hours ahead of international flights and two hours before a domestic departure.

  • United Airlines has direct flights from Princess Juliana International Airport to O'Hare International Airport. Book with this popular airline, then get ready to check out the sights in Chicago — and maybe even more of United States if you have time.

  • Most travellers choose to travel with United Airlines on this route.

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

  • We make it a breeze to book a flight with a stopover. To see all your options for tickets from Princess Juliana International Airport to O'Hare International Airport, uncheck 'Direct flights only.' Then, choose a flight with a stop long enough to explore the city of your choice. Some great stopovers between SXM and ORD include:

    • Philadelphia International Airport

    • Miami International Airport

    • Orlando International Airport

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

  • Right now, $245 is the lowest price we've found for a one-way Princess Juliana International Airport to O'Hare International Airport flight. The best price for a return ticket is $368. Keep in mind that fares may change due to availability when booking.

  • It's usually best to book in advance if you want to find cheap tickets from SXM to ORD. That's because airlines change prices based on demand, which tends to increase closer to the date of departure.

  • If you can be flexible with your travel dates, try using the 'Whole month' tool. It'll find the cheapest price across the month when looking for a flight from Princess Juliana International Airport to O'Hare International Airport.

  • You won't have to check back in every day to see if fares have dropped when you create a Price Alert. We'll notify you the moment there's a change in price on cheap flights from SXM to ORD.

  • Choose your preferred departure and arrival times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to find the best deals on flights from Princess Juliana International Airport to O'Hare International Airport.

Handy information about Princess Juliana International Airport (SXM)

  • Of all flights departing from Princess Juliana International Airport, 54.17% arrive as scheduled at their destination.

  • To reach Princess Juliana International Airport from central Philipsburg, it'll take about 25 minutes if you're travelling by car. Of course, this depends on traffic conditions. It's approximately 11 kilometres from the airport to the city centre.

  • Get your holiday off to a hassle-free start by staying near SXM. Whether you're catching an early flight from Princess Juliana International Airport to O'Hare International Airport or just don't want to be rushed, these hotels are ideal:

Arriving at O'Hare International Airport (ORD)

Getting from O'Hare International Airport (ORD) to central Chicago

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

  • O'Hare International Airport to central Chicago has a drive time of about 35 minutes. It's approximately 40 kilometres away.

  • Travelling on public transport will take you around 55 minutes.

When to fly to O'Hare International Airport (ORD)

  • The quietest month for a flight from Princess Juliana International Airport to O'Hare International Airport is January, while August is the most popular. Choose the best time to visit Chicago based on whether you prefer a more relaxed vibe or a faster pace.

  • Book your flight from Princess Juliana International Airport to O'Hare International Airport for July if you'd like to explore Chicago during its warmest month. You can expect temperatures of between 15ºC and 29ºC.

  • January has average temperatures of between -12ºC and 3ºC. Look for cheap tickets from SXM to ORD sometime around then if you'd rather travel in cooler conditions.

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be explored after you've experienced Chicago. Around 451 kilometres away to the south-east, its best attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in United States. No visit is complete without checking out The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

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