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

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Flight deals from St Maarten to Chicago

Looking for a cheap last-minute deal or the best return flight from St Maarten to Chicago? 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 November.

Direct flights from St Maarten to Chicago

Alternative St Maarten to Chicago routes

Looking for the cheapest, fastest or easiest route from St Maarten to Chicago? You could fly into the following airports instead.

Philipsburg to Chicago: Flight information

The things to know before you go.
Cheapest flight foundSAR 853
Cheapest month to flyNovember
Average flight time5 hrs, 52 mins
Most popular airlineUnited
Average flights per week2

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 SAR 1,916. 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.
United flies direct from St Maarten to Chicago.
As of October 2024, there are 2 flights per week flying from St Maarten to Chicago.
The cheapest month to fly from St Maarten to Chicago is usually October 2024.
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 SAR 1,916.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from St Maarten Airport to Chicago on Sunday, 2 February 2025.
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 October, the average temperature is usually around 11°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, Silver Airways and United offer the cheapest flight tickets to Chicago.

How to find cheap flights to Chicago from St Maarten

Looking for cheap tickets from St Maarten to Chicago? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from St Maarten to Chicago. And with us there are no hidden fees - what you see is what you pay.
  • Compare flight deals to Chicago from St Maarten from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
  • Flex your dates to find the best St Maarten-Chicago ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago from St Maarten.
  • Set up a Price Alert. You can easily track the fare of your cheap St Maarten-Chicago flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Fly without stops. Only interested in direct flights between St Maarten and Chicago? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business class flights from St Maarten and Chicago. We scour the internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for St Maarten to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.
  • Combine your flight to Chicago from St Maarten with hotels and car hire

    Once you've secured your cheap flight ticket from St Maarten to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.


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