MDW to SXM (Chicago to Philipsburg) Flights

Last Minute Flights from MDW to SXM

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
MDWSimpson BayMarch 14 to March 21$1,261
*Prices include taxes and fees

Cheapest MDW to SXM Flights

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
MDWSimpson BayApril 11 to April 21$368
MDWSimpson BayMay 25 to May 30$413
MDWSimpson BayApril 11 to April 21$417
MDWSimpson BayApril 22 to April 28$665
*Prices include taxes and fees
MDW to SXM Flight Details
Origin airport
Midway Intl.
Origin airport IATA code
MDW
Destination airport
Princess Juliana Intl.
Destination airport IATA code
SXM
Distance
2189 mi

Frequently asked questions

What airlines fly direct from MDW to Princess Juliana Intl. Airport (SXM)?
No air carriers fly straight from MDW to Princess Juliana Intl. Airport (SXM). To reach Simpson Bay, book a flight with one stop at least.
How many flights are there from MDW to SXM?
There are approximately 3 flights per day from Chicago, IL (MDW-Midway Intl.) to Philipsburg (SXM-Princess Juliana Intl.), so you have no shortage of ways to get to Simpson Bay. Just select a time and date that works best for you and lock in your airfare.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Philipsburg (SXM-Princess Juliana Intl.)?
Around 5 hours and 48 minutes. Booked on a daytime flight? Request a window seat and stare out at the views below. Or, if you're traveling from Chicago, IL (MDW-Midway Intl.) to Philipsburg (SXM-Princess Juliana Intl.) at nighttime, close your eyes and land in Simpson Bay feeling well rested.
What is the flight distance from Chicago, IL (MDW-Midway Intl.) to Philipsburg (SXM-Princess Juliana Intl.)?
At a distance of 2,200 miles (3,500 1), you'll be cruising the skies for some time during this medium-haul journey. Need legroom? Purchase an aisle seat. Otherwise, go for the window and enjoy the scenery between Chicago and Simpson Bay.
How many morning flights are there from MDW to SXM?
Jet from MDW to SXM with one of the 7 morning flights that are available every week. Delta Air Lines (DL) operates 7 of these services, with the first departing at 6:00AM.
How many afternoon flights are there from MDW to SXM?
Pick one of the 15 weekly afternoon and evening flights from MDW to SXM and sneak in some more sleep. Well-known carrier Delta Air Lines (DL) offers 15 of these later flights departing from 12:45PM.
What is the earliest departure time out of Chicago to Simpson Bay?
The earliest flight flies from MDW at 6:00AM and hits the runway at 1:55PM at SXM. Don't forget to allow yourself ample time in the morning to get to your departure gate.
What is the latest departure time out of Chicago to Simpson Bay?
Reserve a seat on the 6:50PM flight out of MDW, landing at 1:40PM at SXM, and give yourself time to complete those last-minute vacation preparations. This is the latest flight available on this route.
What is the average price from Chicago to Simpson Bay?
Round-trip journeys from MDW to SXM start from around $368. Killer deals don't hang around forever, so have your credit card ready when you spot a bargain. This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Chicago to Philipsburg Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from Chicago to Philipsburg to attend your cousin’s wedding, to pitch a business idea to your boss, or simply treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find our cheapest flights from MDW to SXM, we’ve got you covered here at Flights.com.

We present you with some of the most affordable deals on airfare, so stop that Google flights search. We want you to spend less on your flight from Chicago to Philipsburg, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.

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