Cheap Flights from St Maarten to Chicago Midway

Compare St Maarten to Chicago Midway flight deals

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

Book the best Chicago Midway fare with no extra fees

Flight deals from St Maarten to Chicago Midway

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

Find the cheapest month to fly from St Maarten to Chicago Midway

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

St Maarten to Chicago Midway: Alternative routes

Compare routes from St Maarten to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Philipsburg to Chicago: Flight information

The things to know before you go.
Cheapest flight foundAED 2,525
Cheapest month to flyApril

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

The best price we found for a round-trip flight from St Maarten to Chicago Midway is AED 2,525. 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.
Currently, there are no airlines that fly direct from St Maarten to Chicago Midway. But we found flights with one or more stops from AED 2,525.
There are no flights flying from St Maarten to Chicago Midway, as of November 2024.
The cheapest month to fly from St Maarten to Chicago Midway is usually November 2024.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from St Maarten Airport to Chicago Midway Airport on Thursday, April 17, 2025.
No airlines currently offer direct flights between St Maarten Airport and Chicago Midway Airport. Most routes have one or more stops.
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 Midway 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.
Currently, Delta offers the cheapest flight tickets to Chicago Midway.

How to find cheap flights from St Maarten to Chicago Midway

Looking for cheap flight tickets from St Maarten to Chicago Midway? Skyscanner compares flight prices across more than 1,200 airlines and travel providers.

Regardless of whether you're looking for a one-way ticket to Chicago Midway or a return flight, here are some tips to secure the best flight price and make planning your journey as smooth as possible.

  • Simply hit search. From Emirates and Etihad to international carriers like Air India and Wizz Air, we compare all major airlines with the most popular online travel agents to find the cheapest plane tickets from St Maarten to Chicago Midway. And with us there are no hidden fees - what you see is what you pay.

  • Flex your dates to find the cheapest SXM - MDW flight tickets on Skyscanner. Search for flights but don’t enter the departure date and instead click ‘whole month’. This tool will find the cheapest month and dates to fly to Chicago Midway from St Maarten.

  • Set up a Price Alert for St Maarten-Chicago Midway flight tickets. You can easily track the fare of flights by creating an alert. Whenever prices go down or up, you'll get an email to help make sure you get the best possible flight deal. Or download our app and get price alerts straight to your phone.

  • Fly without stops. Only interested in direct flights between St Maarten and Chicago Midway? Make sure to tick 'Non-stop flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.

Hotels in Chicago Midway

Looking for a hotel in Chicago Midway? Whether you’re looking for a local hotel or a global brand, discover the best prices and exclusive rates for hotels in Chicago Midway by comparing the biggest names in travel.

Car hire in Chicago Midway

If you’re looking for car rental in Chicago Midway, we can help you uncover the best car hire deals. We search hundreds of car hire companies allowing you to instantly compare prices and then book.

Book flight tickets from St Maarten to Chicago Midway with extra peace of mind

Back in 2020, most airlines introduced policies to make travel during COVID-19 as easy as possible. The worst of the pandemic is now over, but some of these policies remain in place for you to take advantage of as you step back out into the world.

  • Find flexible getaways. Some airlines introduced flexible booking policies in 2020 – and many of these are still available. If you book a flexible plane ticket from St Maarten to Chicago Midway, it means your money is still safe if your flights are changed or cancelled due to COVID-19.

  • Get insured. Choose travel cost protection that covers COVID-19, too. It's available at the checkout as you book your flight from St Maarten to Chicago Midway with us.

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