$345 Cheap Flights from Philipsburg (SXM) to Chicago (MDW)

View $345 flight on Wed, Apr 29, 2026Opens in a new window

Popular airlines from Princess Juliana Intl. Airport (SXM) to Chicago Midway Airport (MDW)

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Cheap Flights from Philipsburg to Chicago (SXM-MDW)

Prices were available within the past 7 days and start at $345 for one-way flights and $712 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Jan 30 - Sat, Jan 31
SXM
Saint Martin
MDW
Chicago
$712 Roundtrip, found 4 days ago
$712
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Jan 30 from Saint Martin to Chicago, returning Sat, Jan 31, priced at $712 found 4 days ago
Delta
Fri, Sep 12 - Sun, Sep 14
SXM
Saint Martin
MDW
Chicago
$772 Roundtrip, found 6 days ago
$772
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 12 from Saint Martin to Chicago, returning Sun, Sep 14, priced at $772 found 6 days ago
Delta
Sat, Jan 17 - Sat, Jan 24
SXM
Saint Martin
MDW
Chicago
$777 Roundtrip, found 6 days ago
$777
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Jan 17 from Saint Martin to Chicago, returning Sat, Jan 24, priced at $777 found 6 days ago
Delta
Fri, Oct 17 - Mon, Oct 20
SXM
Saint Martin
MDW
Chicago
$782 Roundtrip, found 3 days ago
$782
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Oct 17 from Saint Martin to Chicago, returning Mon, Oct 20, priced at $782 found 3 days ago
Delta
Fri, Sep 12 - Fri, Sep 19
SXM
Saint Martin
MDW
Chicago
$792 Roundtrip, found 6 days ago
$792
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 12 from Saint Martin to Chicago, returning Fri, Sep 19, priced at $792 found 6 days ago
Delta
Fri, Jan 30 - Sat, Jan 31
SXM
Saint Martin
MDW
Chicago
$832 Roundtrip, found 4 days ago
$832
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Jan 30 from Saint Martin to Chicago, returning Sat, Jan 31, priced at $832 found 4 days ago
Delta
Wed, Sep 10 - Sun, Sep 14
SXM
Saint Martin
MDW
Chicago
$857 Roundtrip, found 6 days ago
$857
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Sep 10 from Saint Martin to Chicago, returning Sun, Sep 14, priced at $857 found 6 days ago
Delta
Sat, Jan 17 - Sat, Jan 24
SXM
Saint Martin
MDW
Chicago
$861 Roundtrip, found 6 days ago
$861
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Jan 17 from Saint Martin to Chicago, returning Sat, Jan 24, priced at $861 found 6 days ago
Delta
Fri, Sep 12 - Sat, Sep 13
SXM
Saint Martin
MDW
Chicago
$877 Roundtrip, found 6 days ago
$877
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 12 from Saint Martin to Chicago, returning Sat, Sep 13, priced at $877 found 6 days ago
Southwest Airlines
Sat, May 9 - Sat, May 16
SXM
Saint Martin
MDW
Chicago
$947 Roundtrip, found 2 days ago
$947
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, May 9 from Saint Martin to Chicago, returning Sat, May 16, priced at $947 found 2 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $603
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $603
Flights from Philipsburg (SXM) to Chicago (MDW)
Origin airport
Princess Juliana Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$712
Distance
2189 mi

Philipsburg to Chicago Flights

The cheapest times to fly from Philipsburg to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Philipsburg to Chicago are during the month of January. You can find some of the cheapest flights from Philipsburg to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Philipsburg to Chicago

Sunday is one of the best days to book for cheap flights from Philipsburg to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Philipsburg to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Philipsburg to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $345 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Philipsburg to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Philipsburg to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Princess Juliana Intl. Airport (SXM) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $345 or cheap return flight from $712 from Princess Juliana Intl. Airport (SXM) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Princess Juliana Intl. Airport (SXM) to Midway Intl. Airport (MDW)?
Planning your getaway for January is a great way to save, as it's the cheapest month for flights between SXM and MDW. You'll typically find the lowest prices during the off-season.
What is the cheapest airline that flies from Princess Juliana Intl. Airport (SXM) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll take you from SXM to MDW. Then, sort your results by "Price (lowest to highest)" to pick up the best deal available.
How many flights per day from Princess Juliana Intl. Airport (SXM) to Midway Intl. Airport (MDW)?
You'll have to take a flight with a layover when traveling from Princess Juliana Intl. Airport (SXM) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, simply filter your search to include one or more stops to find an option that works for you.
What day of the week has the most flights from SXM to MDW?
Usually you'll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* However, this can change depending on the season, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Princess Juliana Intl. Airport (SXM) to Midway Intl. Airport (MDW)?
To land at Midway Intl. Airport (MDW) without delays, choose a flight that leaves from Princess Juliana Intl. Airport (SXM) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Princess Juliana Intl. Airport (SXM)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Princess Juliana Intl. Airport (SXM). Compare the available options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Princess Juliana Intl. Airport (SXM) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from SXM to MDW are usually more expensive. To secure the best rates, start searching for flights as soon as possible. That said, if your travel plans are flexible, you may land a cheap fare right before your trip.
Is it cheaper to book a SXM to MDW flight and hotel package?
You can save money by securing a SXM to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one convenient place. Once you've selected your preferred accommodations and flights, you can add extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Princess Juliana Intl. Airport (SXM) to Midway Intl. Airport (MDW)?
Generally, it's possible to reschedule or cancel your SXM to MDW flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more information on our Customer Service portal.

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*Available to One Key members.