$264 Cheap Flights from Philipsburg (SXM) to Chicago (ORD)

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Cheap flights from Philipsburg (SXM) to Chicago (ORD)

Prices were available within the past 7 days and start at $264 for one-way flights and $370 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Fri, Oct 25 - Tue, Nov 12
SXM
Saint Martin
ORD
Chicago
$370 Roundtrip, found 6 days ago
$370
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Fri, Oct 25 from Saint Martin to Chicago, returning Tue, Nov 12, priced at $370 found 6 days ago
Spirit Airlines
Wed, Oct 23 - Wed, Oct 30
SXM
Saint Martin
ORD
Chicago
$384 Roundtrip, found 6 days ago
$384
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Oct 23 from Saint Martin to Chicago, returning Wed, Oct 30, priced at $384 found 6 days ago
Spirit Airlines
Mon, Oct 21 - Tue, Nov 12
SXM
Saint Martin
ORD
Chicago
$391 Roundtrip, found 6 days ago
$391
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Mon, Oct 21 from Saint Martin to Chicago, returning Tue, Nov 12, priced at $391 found 6 days ago
Spirit Airlines
Fri, Oct 25 - Sat, Nov 9
SXM
Saint Martin
ORD
Chicago
$400 Roundtrip, found 6 days ago
$400
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Fri, Oct 25 from Saint Martin to Chicago, returning Sat, Nov 9, priced at $400 found 6 days ago
Spirit Airlines
Wed, Oct 23 - Mon, Nov 4
SXM
Saint Martin
ORD
Chicago
$403 Roundtrip, found 6 days ago
$403
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Oct 23 from Saint Martin to Chicago, returning Mon, Nov 4, priced at $403 found 6 days ago
Spirit Airlines
Sat, Oct 26 - Tue, Nov 12
SXM
Saint Martin
ORD
Chicago
$408 Roundtrip, found 6 days ago
$408
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Sat, Oct 26 from Saint Martin to Chicago, returning Tue, Nov 12, priced at $408 found 6 days ago
Spirit Airlines
Mon, Oct 21 - Mon, Nov 4
SXM
Saint Martin
ORD
Chicago
$410 Roundtrip, found 6 days ago
$410
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Mon, Oct 21 from Saint Martin to Chicago, returning Mon, Nov 4, priced at $410 found 6 days ago
Spirit Airlines
Wed, Oct 23 - Sat, Nov 9
SXM
Saint Martin
ORD
Chicago
$414 Roundtrip, found 6 days ago
$414
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Oct 23 from Saint Martin to Chicago, returning Sat, Nov 9, priced at $414 found 6 days ago
Spirit Airlines
Mon, Oct 21 - Sat, Nov 9
SXM
Saint Martin
ORD
Chicago
$421 Roundtrip, found 6 days ago
$421
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Mon, Oct 21 from Saint Martin to Chicago, returning Sat, Nov 9, priced at $421 found 6 days ago
Spirit Airlines
Wed, Oct 23 - Fri, Nov 8
SXM
Saint Martin
ORD
Chicago
$433 Roundtrip, found 6 days ago
$433
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Oct 23 from Saint Martin to Chicago, returning Fri, Nov 8, priced at $433 found 6 days ago
Flight from Philipsburg to Chicago (SXM - ORD) route information
Origin airport
Princess Juliana Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Copa, Delta, JetBlue Airways, United
Roundtrip price
$370
Distance
2204 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 October. 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 2024. You can also book with separate airlines for your outbound and return journeys, from $264 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 is a one-way flight from SXM to O'Hare Airport?
You can score one-way Sint Maarten flights to Chicago starting from just $285. This is based on the best fare found on Expedia for this route with a departure date in the next three months and was last updated on September 23 2024 and has not changed since. This airfare is for an Air Canada service, leaving from SXM on December 18 2024 and arriving at ORD.
Is it cheaper to buy a plane ticket from Princess Juliana Intl. Airport to ORD last minute?
Being the spontaneous type is a fabulous way to discover the world, but it’s not necessarily the ideal way to score a cheap airfare. Think about booking your SXM to O’Hare Airport journey ahead of time instead of waiting till the last minute. Based on flight pricing and demand studies in 2022, we have found that the best time to book domestic flights is between 28 – 35 days ahead of the departure date, and international flights three to four months in advance. We recommend saving that spontaneity for when you get to O’Hare Airport!
What is the cheapest airline flying from Princess Juliana Intl. Airport (SXM) to O'Hare Intl. Airport (ORD) in the next 90 days?
The cheapest carrier flying from Sint Maarten to Chicago found on Expedia is Air Canada, which has fares starting from $285. This price is based on fares found on Expedia with a departure date within the next 90 days. The flight jets off from Princess Juliana Intl. Airport (SXM) on December 18 2024 and arrives at O’Hare Airport. The pricing information was updated on September 23 2024 and has not changed since.
What's the cheapest price for a flight from Princess Juliana Intl. Airport to ORD next month?
The best price for a flight from Sint Maarten to Chicago within the next month is $308. If you’re planning to take off soon, now’s the time to reel in this fare. This ticket price was found after searching all available flights on Expedia with a departure date within the next 30 days. This airfare is for a one-way JetBlue Airways flight leaving Princess Juliana Intl. Airport on October 4 2024 and coming in to land at O’Hare Intl. Airport (ORD). This price was last updated on September 23 2024 and has not changed since.
What airports do you fly into for Chicago from Simpson Bay?
From Simpson Bay, you can travel to Chicago through O’Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT). It’s a good idea to check which airport is the right option for you before you make a decision. If you settle on O’Hare Intl. Airport (ORD), it’s roughly 16 mi northwest of the center of the city. Use the dough you save when booking your airfare with Expedia to uncover the city’s awesome sights, such as Wrigley Field and Millennium Park.
Can I change the date of my flight from Princess Juliana Intl. Airport (SXM) to O'Hare Airport?
It’s easy to make changes to your Princess Juliana Intl. Airport (SXM) to O’Hare Airport journey yourself. Simply go to the Expedia Trips portal and choose “change flight.” Look around for new flights and lock in the one that fits your plans. You’ll see an estimate of any flight change costs. You can also find your way to our Customer Service portal to connect with our Virtual Agent and get answers to all your questions.
Chicago nearby Airports

Chicago

Philipsburg to Midway Intl.
$300.63
*Available to One Key members.