Cheap Flights from Chicago to St Maarten

Compare Chicago to St Maarten flight deals

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

Book the best St Maarten fare with no extra fees

Flight deals from Chicago to St Maarten

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

Find the cheapest month to fly from Chicago to St Maarten

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

Direct flights from Chicago to St Maarten

Chicago to St Maarten: Alternative routes

Compare routes from Chicago 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 foundRs26,167
Cheapest month to flyMarch
Average flight time5 hrs
Most popular airlineAmerican Airlines
Average flights per week3

Finding cheap flights from Chicago to St Maarten: Frequently asked questions

The best price we found for a return flight from Chicago to St Maarten is Rs82,514. 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 to St Maarten.
American Airlines and United fly direct from Chicago to St Maarten.
As of February 2026, there are 3 flights per week flying from Chicago to St Maarten.
The cheapest month to fly from Chicago to St Maarten is usually March.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to St Maarten Airport on Sunday, 8 March 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.

Flying from Chicago to Princess Juliana International Airport (SXM): What you need to know

  • Book a direct Chicago to Princess Juliana International Airport flight and you'll be in the air for around 5 hours 5 minutes.

  • The timezone in Philipsburg is UTC-4, which is one hour ahead of Chicago. Princess Juliana International Airport is located in Philipsburg.

  • For hassle-free travel, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This ensures you have enough time to catch your flight from Chicago to SXM.

  • In high season, allow for extended wait times and be there earlier. Aim for at least two hours ahead for domestic flights and as much as four hours for international trips.

Airports in Chicago

O'Hare International Airport (ORD)

  • You can book a direct flight from Chicago to Princess Juliana International Airport (SXM) departing from O'Hare International Airport (ORD).

  • United Airlines is a well-known carrier that offers direct flights from Chicago to Princess Juliana International Airport leaving from ORD.

  • United Airlines is the airline with the highest number of bookings for flights from ORD to SXM.

  • The carrier with the top on-time arrival rate on this route is United Airlines.

  • ORD is about 40 kilometres from central Chicago. If you're catching a cab, ride-sharing or driving from the centre, it'll take 35 minutes or so to get there, depending on the traffic. If you're planning to take public transport, expect the travel time to be around 55 minutes.

  • Want a leisurely start to your holiday? Stay near O'Hare International Airport. Whether you're boarding an early flight from Chicago to Princess Juliana International Airport or just don't want to be rushed, these hotels are the answer:

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

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • MDW is about 19 kilometres from central Chicago. It'll take you 20 minutes or so to get to the airport if you're driving from the city centre. Public transport takes roughly 45 minutes.

  • Got an early start? Think about checking in to one of these hotels near Chicago Midway International Airport the day before your Chicago to SXM flight:

  • Chicago Midway International Airport has an on-time performance of 77.88%. This figure highlights how often flights that depart from this airport arrive at their destination on schedule.

  • The address for MDW is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is roughly 137 kilometres from central Chicago. Driving from the city centre to the terminal takes about 1 hour 25 minutes. If you're planning to use public transport, expect a journey time of around 4 hours 15 minutes.

  • Sleep a little longer and still make your Chicago to Princess Juliana International Airport flight with plenty of time to spare. These hotels near Chicago Rockford International Airport make getting to the terminal a breeze if you're flying out first thing:

  • Airports have an on-time performance rating that measures how often flights get to their destinations without delays. At RFD, that rate is 76.19%.

  • You'll find Chicago Rockford International Airport at 2 Airport Cir.

About Princess Juliana International Airport (SXM)

How to find the cheapest flights from Chicago to Princess Juliana International Airport (SXM)

  • Rs26,167 is the best price for a one-way ticket from Chicago to Princess Juliana International Airport. A return flight starts from Rs82,514. These prices may change depending on availability.

  • To score cheap flights from Chicago to SXM, book your ticket four months before your departure date.

  • The best month for landing cheap Chicago to Princess Juliana International Airport tickets is September. Use the 'Whole month' tool to compare prices, then choose the dates offering the lowest fares.

  • Save time looking for cheap flight tickets from Chicago to SXM by creating a Price Alert. We'll send you an email or notification on the app when a lower fare pops up.

  • Tailor your trip using filters. Select your arrival and departure times, airlines and total journey duration. You can also sort the results by 'Fastest,' 'Cheapest' or 'Best' flights from Chicago to Princess Juliana International Airport.

The best time to fly from Chicago to Princess Juliana International Airport (SXM)

  • It's time to decide when to book your flight from Chicago to Princess Juliana International Airport (SXM). July is when most people travel to Philipsburg. If you prefer a quieter vibe, think about going in April.

  • The warmest month in Philipsburg is September, with temperatures ranging between 25ºC and 29ºC. Book your Chicago to SXM flight ticket then if that's your definition of good weather.

  • If you want to travel in cooler conditions, look for a cheap ticket from Chicago to Princess Juliana International Airport in February when temperatures are between 21ºC and 26ºC.

More about Philipsburg

  • Once you've booked your flight from Chicago to Princess Juliana International Airport, find a hotel that offers the right mix of comfort and location. Make one of these accommodation options your base for exploring Philipsburg:

  • Your Philipsburg visit won't be complete without checking out the sights. Big-name attractions worth exploring include Great Bay Beach, Private Yacht Charter N.V. and Wander Route Coastal Trail.

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