174 € Cheap Flights from St Maarten to Chicago

Compare St Maarten to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

Flight deals from St Maarten Airport to Chicago

Looking for a cheap last-minute deal or the best return flight from St Maarten Airport to Chicago? If you want to travel next month, return fares start from 203 €. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from St Maarten to Chicago

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

Direct flights from St Maarten to Chicago

Philipsburg to Chicago: Flight information

The things to know before you go.
Cheapest flight found174 €
Cheapest month to flyFebruary
Average flight time5 hrs, 52 mins
Most popular airlineAmerican Airlines
Average flights per week3

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from St Maarten to Chicago is 174 €. 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 52 minutes is the average flight time from St Maarten to Chicago.
American Airlines and United fly direct from St Maarten to Chicago.
As of February 2026, there are 3 flights per week flying from St Maarten to Chicago.
The cheapest month to fly from St Maarten to Chicago is usually February.
If you're flying from St Maarten Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from 174 €.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from St Maarten Airport to Chicago on Friday, 20 February 2026.
Yes – the average flight time is 5 hours and 52 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 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.
In February, the average temperature is usually around -2°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Spirit Airlines and United offer the cheapest flight tickets to Chicago.

Travelling from Princess Juliana International Airport (SXM) to Chicago: what you need to know

  • The average length of a direct flight from Princess Juliana International Airport to Chicago is 5 hours 5 minutes.

  • Chicago is one hour behind Philipsburg, where Princess Juliana International Airport is located. Chicago runs on the UTC-5 timezone.

  • Leave plenty of time to make your SXM to Chicago flight. Generally, it's best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • You can book a direct Princess Juliana International Airport to Chicago ticket. Begin your journey at SXM and land at O'Hare International Airport (ORD).

  • Check out the deals with United Airlines. This airline has direct flights from Princess Juliana International Airport to Chicago.

  • Central Philipsburg to SXM is around 6 kilometres. Depending on traffic, it'll take about 25 minutes to get there if you're catching a cab, ride-sharing or driving.

  • Want an easy start to your trip? Stay near SXM. Whether you have an early flight from Princess Juliana International Airport to Chicago or want to avoid feeling rushed, these hotels are a convenient choice:

  • 54.17% of flights leaving from Princess Juliana International Airport land at their destination on time.

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

  • 127 € is currently the lowest price for a one-way Princess Juliana International Airport to Chicago flight. Return plane tickets start at 174 €. These prices may change based on availability.

  • To find cheap flights from SXM to Chicago, book as early as possible. Airlines tend to offer their most competitively priced fares when tickets first go on sale.

  • The 'Whole month' tool will show you the cheapest tickets from Princess Juliana International Airport to Chicago across the entire month. It's a great way to find a bargain if your travel plans are flexible.

  • Finding a cheap flight from SXM to Chicago is easy with Price Alerts. All you need to do is set up one of these automatic notifications and we'll notify you as soon as a deal gets even better.

  • Find a cheap flight from Princess Juliana International Airport to Chicago with the help of our filters. Select your ideal duration, departure time and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It takes around 35 minutes to reach the centre driving.

  • If you're using public transport, expect a journey time of around 55 minutes.

  • The last thing you want is a lengthy journey to your hotel if you're landing late on a flight from Princess Juliana International Airport to Chicago. Stay at one of these accommodation options near ORD instead:

  • Get on the fast track to adventure by picking up an O'Hare International Airport rental car. Grab a set of wheels from Routes Car Rentals, Dollar or Budget and explore beyond Chicago's usual tourist stops.

  • To secure the lowest price, book your vehicle from O'Hare International Airport around four weeks ahead of your flight from SXM to Chicago.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • The centre of Chicago is about 19 kilometres from Chicago Midway International Airport (MDW). After your flight from Princess Juliana International Airport to Chicago has hit the runway and you've made your way through the terminal, expect a drive of about 20 minutes.

  • Public transport will get you there in about 45 minutes.

  • After stepping off your SXM to Chicago flight, settle in at a hotel close to MDW. These are some comfortable options that'll help you get into relaxation mode:

  • The quickest way to reach your destination is with a Chicago Midway International Airport rental car. Grab a set of wheels from Dollar, Hertz or Budget and make a speedy getaway.

  • Avoid potential price surges. Reserving your ride four weeks ahead of your arrival at MDW will help you save.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 137 kilometres from central Chicago. It takes about 1 hour 25 minutes to get to the city centre by cab or ride-share once you've hopped off your flight from Princess Juliana International Airport to Chicago.

  • The journey takes roughly 4 hours 15 minutes if you use public transport.

  • Enjoy a low-stress, comfortable start to your trip by checking in to a hotel near RFD after your SXM to Chicago flight. Recover from your travel day or simply give yourself time to find your footing in a new city at:

  • Start your trip without stressing about how to get to where you're going with a Chicago Rockford International Airport rental car. Find your perfect set of wheels with trusted suppliers here like Budget, Alamo and National.

  • Rental agencies sometimes offer deals on early bookings, so secure your vehicle from RFD a few weeks in advance of your flight from Princess Juliana International Airport to Chicago. A little prep work can make a big difference in cost.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

  • Before booking your flights from Princess Juliana International Airport to Chicago, consider which time of year works best for you. Peak season in Chicago offers a bustling atmosphere and plenty of things to do, while low season brings better deals on hotels and smaller crowds.

  • Book a Princess Juliana International Airport to Chicago plane ticket with a departure in July if you're eager to explore the city during its warmest month. You can expect temperatures to range from 15ºC (59ºF) to 29ºC (84ºF).

  • Search for cheap tickets from SXM to Chicago in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

  • When it comes to searching for somewhere to lay your head, you'll find the most popular stays in Chicago right here. Explore these hotels as soon as you've booked your flight from Princess Juliana International Airport to Chicago:

  • There are so many things to do and see in this city it can be tricky to work out where to begin. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are top sights which should feature on any good Chicago itinerary.

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be explored once you've taken in the sights of 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. Experience major highlights starting with 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.