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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

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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.
Philipsburg.469 € per passenger.Departing Thu, 2 May, returning Wed, 15 May.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Thu, 2 May, arriving in St Maarten.Inbound indirect flight with Spirit Airlines, departs from St Maarten on Wed, 15 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From 469 €, select.
Philipsburg.580 € per passenger.Departing Thu, 18 Jul, returning Tue, 23 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Thu, 18 Jul, arriving in St Maarten.Inbound indirect flight with Delta, departs from St Maarten on Tue, 23 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From 580 €, select.
Philipsburg.603 € per passenger.Departing Sat, 22 Jun, returning Thu, 27 Jun.Return flight with Spirit Airlines and Air Century.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 22 Jun, arriving in St Maarten.Inbound indirect flight with Air Century, departs from St Maarten on Thu, 27 Jun, arriving in Chicago Midway.Price includes taxes and charges.From 603 €, select.
Philipsburg.688 € per passenger.Departing Sat, 11 Jan, returning Sat, 18 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 11 Jan, arriving in St Maarten.Inbound indirect flight with Delta, departs from St Maarten on Sat, 18 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From 688 €, select.

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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 May.
Apr
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May
from 469 €
Jun
from 603 €
Jul
from 580 €
Aug
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Sep
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Oct
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Nov
from 1.031 €
Dec
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Jan
from 688 €
Feb
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Mar
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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 found469 €
Cheapest month to flyMay
Average flight time5 hrs, 2 mins
Most popular airlineUnited
Average flights per week9

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 469 €. 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 2 minutes is the average flight time from Chicago to St Maarten.
United flies direct from Chicago to St Maarten.
As of April 2024, there are 9 flights per week flying from Chicago to St Maarten.
The cheapest month to fly from Chicago to St Maarten is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to St Maarten Airport on Thursday, 2 May 2024.
Yes – the average flight time is 5 hours and 2 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 St Maarten is around 40 days in advance, so don’t leave your flight to the last minute.

How to find cheap flights to Philipsburg (SXM) from Chicago (CHI)in 2024

Looking for cheap tickets from Chicago to St Maarten? Return tickets start from 469 € and one-way flights to St Maarten from Chicago start from 92 €


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 Chicago to St Maarten. And with us there are no hidden fees - what you see is what you pay.
  • Compare flight deals to Philipsburg from Chicago from over 1,000 providers. Then choose the cheapest or fastest plane tickets. Flight tickets to Philipsburg start from 92 € one-way.
  • Set up a Price Alert. You can easily track the fare of your cheap Chicago-St Maarten 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.
  • Flex your dates to find the best CHI-SXM 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 St Maarten from Chicago.
  • Fly without stops. Only interested in direct flights between Chicago and St Maarten? 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. Airlines that fly direct include: United
  • Find the cheapest Business class flights from Chicago and St Maarten. We scour the internet for the best Business, Premium Economy and First Class flight fares to Philipsburg, 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 Chicago to St Maarten 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.
  • Flexible on when you travel? The cheapest month to fly from Chicago to St Maarten is May.
  • Search for cheap flights regardless of where you are. To get the best flight booking experience when out and about, download the app and search for plane tickets between Chicago and St Maarten whenever you want.

Combine your flight to St Maarten from Chicago with hotels and car hire

Once you've secured your cheap flight ticket from Chicago to St Maarten, discover the best prices and exclusive rates for hotels in Philipsburg 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.


Plan the rest of your trip from Chicago to Philipsburg

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