Skyscanner home

Cheap Flights from Chicago (CHIA) to Philipsburg (SXM)

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 Airport? If you want to travel next month, return fares start from $587. Find the lowest prices on one-way and return tickets right here.
Philipsburg.$550 per passenger.Departing Fri, 21 Aug, returning Thu, 27 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 21 Aug, arriving in St Maarten.Inbound indirect flight with Southwest Airlines, departs from St Maarten on Thu, 27 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $550, select.
Philipsburg.$550 per passenger.Departing Fri, 28 Aug, returning Thu, 10 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Fri, 28 Aug, arriving in St Maarten.Inbound indirect flight with Southwest Airlines, departs from St Maarten on Thu, 10 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $550, select.
Philipsburg.$587 per passenger.Departing Sat, 3 Oct, returning Thu, 8 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 3 Oct, arriving in St Maarten.Inbound indirect flight with Southwest Airlines, departs from St Maarten on Thu, 8 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $587, select.
Philipsburg.$587 per passenger.Departing Thu, 3 Sep, returning Mon, 7 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 3 Sep, arriving in St Maarten.Inbound indirect flight with Southwest Airlines, departs from St Maarten on Mon, 7 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $587, select.
Philipsburg.$587 per passenger.Departing Mon, 13 Jul, returning Tue, 14 Jul.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 13 Jul, arriving in St Maarten.Inbound indirect flight with Southwest Airlines, departs from St Maarten on Tue, 14 Jul, arriving in Chicago Midway.Price includes taxes and charges.From $587, select.
Philipsburg.$587 per passenger.Departing Tue, 30 Jun, returning Thu, 2 Jul.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 30 Jun, arriving in St Maarten.Inbound indirect flight with Southwest Airlines, departs from St Maarten on Thu, 2 Jul, arriving in Chicago Midway.Price includes taxes and charges.From $587, select.
Philipsburg.$701 per passenger.Departing Fri, 24 Jul, returning Sat, 1 Aug.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Fri, 24 Jul, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Sat, 1 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $701, select.
Philipsburg.$802 per passenger.Departing Fri, 12 Jun, returning Sat, 20 Jun.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Fri, 12 Jun, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Sat, 20 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $802, select.
Philipsburg.$832 per passenger.Departing Fri, 27 Nov, returning Sat, 5 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 Sat, 5 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From $832, select.
Philipsburg.$837 per passenger.Departing Sun, 25 Oct, returning Sun, 1 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 Sun, 1 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $837, select.
Philipsburg.$840 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 $840, select.
Philipsburg.$842 per passenger.Departing Sat, 14 Nov, returning Sat, 21 Nov.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Sat, 14 Nov, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Sat, 21 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $842, select.
Philipsburg.$889 per passenger.Departing Fri, 15 Jan, returning Sat, 23 Jan.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Fri, 15 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 $889, select.
Philipsburg.$902 per passenger.Departing Sat, 26 Sep, returning Sat, 10 Oct.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 26 Sep, arriving in St Maarten.Inbound indirect flight with Southwest Airlines, departs from St Maarten on Sat, 10 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $902, select.
Philipsburg.$970 per passenger.Departing Sat, 10 Apr, returning Fri, 16 Apr.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Sat, 10 Apr, arriving in St Maarten.Inbound indirect flight with Copa, departs from St Maarten on Fri, 16 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From $970, select.
Philipsburg.$1,035 per passenger.Departing Fri, 5 Mar, returning Wed, 10 Mar.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Fri, 5 Mar, arriving in St Maarten.Inbound indirect flight with Air Canada, departs from St Maarten on Wed, 10 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,035, select.

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 August.
Jun
from $802
Jul
from $587
Aug
from $550
Sep
from $587
Oct
from $587
Nov
from $842
Dec
from $840
Jan
from $889
Feb
from $1,062
Mar
from $1,035
Apr
from $970
May
Find prices

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.

St Maarten

7km from central Philipsburg
ClosestCheapest
from $550
Search flights

Chicago to Philipsburg: Flight information

The things to know before you go.
Cheapest flight found$550
Cheapest month to flyAugust
Average flight time4 hrs, 59 mins
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 $550. 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.
4 hours and 59 minutes is the average flight time from Chicago to St Maarten.
American Airlines and United fly direct from Chicago to St Maarten.
As of June 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 August.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to St Maarten Airport on Friday, 21 August 2026.
Yes – the average flight time is 4 hours and 59 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.

Travelling from Chicago to Sint Maarten Princess Juliana Intl Airport (SXM): What you need to know

  • The average duration of a direct Chicago to Sint Maarten Princess Juliana Intl Airport flight is 5 hours 10 minutes.

  • Sint Maarten Princess Juliana Intl Airport is located in Philipsburg. The city is in the UTC-4 timezone and is two hours ahead of Chicago.

  • Give yourself enough time to make your flight from Chicago to SXM. A good rule of thumb is to arrive two hours before international departures and an hour ahead for domestic flights.

  • Getting away during a peak time like July? High seasons (like Thanksgiving, Christmas and New Year) can add another hour at security. Be extra safe and arrive up to four hours before an international flight and two hours before a domestic departure.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) is a convenient option for travelling directly to your destination. Nonstop flights from Chicago to Sint Maarten Princess Juliana Intl Airport (SXM) depart from this terminal.

  • When departing from ORD, you can take a direct flight from Chicago to Sint Maarten Princess Juliana Intl Airport with United Airlines.

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

  • Among carriers on this route, United has the highest rate of on-time arrivals.

  • ORD is around 27 kilometres from central Chicago. If you're driving, catching a taxi or ride-sharing from the centre, it'll take 30 minutes or so to get there, depending on traffic conditions. If you're taking public transport, expect the trip time to be around 45 minutes.

  • In search of a convenient hotel near Chicago O'Hare International Airport? If you're catching an early flight from Chicago to Sint Maarten Princess Juliana Intl Airport, these accommodation options will put you moments from your departure lounge:

  • When it comes to the on-time performance of Chicago O'Hare International Airport, data shows 70% of flights meet their scheduled arrival time.

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

Chicago Midway International Airport (MDW)

  • You can arrive at MDW from the centre of Chicago in about 25 minutes by car (depending on traffic). The ride on public transport will take roughly 30 minutes to travel the 16 kilometres or so.

  • Start your holiday sooner with an additional night away from home. Before your Chicago to SXM flight, kick back in one of these hotels close to Chicago Midway International Airport:

  • Chicago Midway International Airport has an on-time performance of 76%. This figure provides insight into how often flights that leave from this airport make it to their destination on time.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • From central Chicago, RFD is around 145 kilometres away. It takes roughly 1 hour 40 minutes to reach the airport by car and 2 hours or so if you're on public transport.

  • Rest a little longer, move a little slower, and still make your Chicago to Sint Maarten Princess Juliana Intl Airport flight without having to rush. These accommodation options near Chicago Rockford International Airport make departure day effortless if you're setting off early:

  • Flights departing from RFD arrive at their final stop within the scheduled time frame 71% of the time.

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

About Sint Maarten Princess Juliana Intl Airport (SXM)

Getting from Sint Maarten Princess Juliana Intl Airport (SXM) to central Philipsburg

  • Sint Maarten Princess Juliana Intl Airport to central Philipsburg is roughly 6 kilometres. If you're getting a taxi or renting a car, do some research to make your trip as smooth as possible. Journey times may vary based on the time of day and traffic conditions.

  • It takes around 20 minutes if you're using public transport.

How to find the cheapest flights from Chicago to Sint Maarten Princess Juliana Intl Airport (SXM)

  • $211 is the lowest price for a one-way ticket from Chicago to Sint Maarten Princess Juliana Intl Airport. Return flights start from $550. These fares can change depending on availability and demand.

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

  • September is when you're most likely to land a good deal on a Chicago to Sint Maarten Princess Juliana Intl Airport ticket. If you want to travel during a different time of year, the 'Whole month' tool will show you the lowest prices for every month.

  • Never miss a deal on plane tickets from Chicago to SXM by creating a Price Alert. We'll send you an email or notification through the app when a new discounted fare appears.

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

The best time to fly from Chicago to Sint Maarten Princess Juliana Intl Airport (SXM)

  • December is the quietest month for flights from Chicago to Sint Maarten Princess Juliana Intl Airport (SXM), while March is the busiest. Find the ideal time to go to Philipsburg based on whether you like a laid-back vibe or a more bustling atmosphere.

  • The warmest month in Philipsburg is September, with temperatures ranging between 25ºC (77ºF) and 29ºC (84ºF). Book your Chicago to SXM plane ticket then if that's your definition of good weather.

  • Look for cheap tickets from Chicago to Sint Maarten Princess Juliana Intl Airport in February if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between 21ºC (70ºF) and 26ºC (79ºF).

More about Philipsburg

  • When it comes to searching for somewhere to rest your head, you'll find the most popular stays in Philipsburg right here. Browse these options as soon as you've booked your flight from Chicago to Sint Maarten Princess Juliana Intl Airport:

  • Your Philipsburg trip wouldn't be complete without a bit of sightseeing. Leading attractions that are worth your time include Great Bay Beach, Guana Bay Beach and Yoda Guy Movie Exhibit.

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.