$162 Cheap Flights from Philipsburg (SXM) to Chicago (ORD)

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Cheap Flights from Philipsburg to Chicago (SXM-ORD)

Prices were available within the past 7 days and start at $162 for one-way flights and $231 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Jun 1 - Sun, Jun 2
SXM
Philipsburg
ORD
Chicago
$231 Roundtrip, found 6 days ago
$231
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jun 1 from Philipsburg to Chicago, returning Sun, Jun 2, priced at $231 found 6 days ago
Frontier Airlines
Sat, Jun 1 - Tue, Jun 4
SXM
Philipsburg
ORD
Chicago
$262 Roundtrip, found 5 days ago
$262
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Jun 1 from Philipsburg to Chicago, returning Tue, Jun 4, priced at $262 found 5 days ago
Spirit Airlines
Mon, Jun 3 - Wed, Jun 5
SXM
Philipsburg
ORD
Chicago
$302 Roundtrip, found 5 days ago
$302
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Mon, Jun 3 from Philipsburg to Chicago, returning Wed, Jun 5, priced at $302 found 5 days ago
Frontier Airlines
Sat, Jun 1 - Wed, Jun 5
SXM
Philipsburg
ORD
Chicago
$307 Roundtrip, found 6 days ago
$307
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jun 1 from Philipsburg to Chicago, returning Wed, Jun 5, priced at $307 found 6 days ago
Spirit Airlines
Wed, Jun 5 - Wed, Jun 12
SXM
Philipsburg
ORD
Chicago
$311 Roundtrip, found 5 days ago
$311
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Jun 5 from Philipsburg to Chicago, returning Wed, Jun 12, priced at $311 found 5 days ago
Spirit Airlines
Sat, Sep 7 - Sat, Sep 14
SXM
Philipsburg
ORD
Chicago
$319 Roundtrip, found 4 hours ago
$319
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, Sep 7 from Philipsburg to Chicago, returning Sat, Sep 14, priced at $319 found 4 hours ago
Frontier Airlines
Fri, Jun 21 - Fri, Jun 28
SXM
Philipsburg
ORD
Chicago
$322 Roundtrip, found 3 days ago
$322
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Jun 21 from Philipsburg to Chicago, returning Fri, Jun 28, priced at $322 found 3 days ago
Spirit Airlines
Mon, Jun 10 - Tue, Jun 25
SXM
Philipsburg
ORD
Chicago
$326 Roundtrip, found 1 day ago
$326
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Jun 10 from Philipsburg to Chicago, returning Tue, Jun 25, priced at $326 found 1 day ago
Spirit Airlines
Sat, Jun 1 - Tue, Jun 4
SXM
Philipsburg
ORD
Chicago
$329 Roundtrip, found 5 days ago
$329
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, Jun 1 from Philipsburg to Chicago, returning Tue, Jun 4, priced at $329 found 5 days ago
Spirit Airlines
Wed, Jun 5 - Fri, Jun 7
SXM
Philipsburg
ORD
Chicago
$330 Roundtrip, found 5 days ago
$330
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Jun 5 from Philipsburg to Chicago, returning Fri, Jun 7, priced at $330 found 5 days ago
Flights from Philipsburg (SXM) to Chicago (ORD)
Origin airport
Princess Juliana Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Copa, Delta, Frontier Airlines, JetBlue Airways, Spirit Airlines, United
Roundtrip price
$231
Distance
2204 mi
Average flight time
6 hours 44 mins

Philipsburg to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Philipsburg to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Philipsburg to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from SXM to ORD today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is $162 now!

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 $179. 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 May 23 2024 and has not changed since. This airfare is for an Frontier Airlines service, leaving from SXM on June 2 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 Frontier Airlines, which has fares starting from $179. 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 June 2 2024 and arrives at O’Hare Airport. The pricing information was updated on May 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 $179. 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 Frontier Airlines flight leaving Princess Juliana Intl. Airport on June 2 2024 and coming in to land at O’Hare Intl. Airport (ORD). This price was last updated on May 23 2024 and has not changed since.
Can I find cheap nonstop flights from Princess Juliana Intl. Airport (SXM) to ORD in the next three months?
Your next getaway doesn’t have to blow a hole in your budget. We’ve come across a roundtrip nonstop flight from Sint Maarten to Chicago in the next 90 days for $590. This price is based on airfares found on Expedia with a departure date in the next three months and was last updated on May 23 2024. The flight via United departs from SXM on June 1 2024 and arrives at ORD. It has a return date of June 8 2024.If you want to track down nonstop cheap flights leaving from SXM to ORD, use our filters after you’ve hit search. Just click on “Nonstop” under “Filter by” on the left side of the page to browse your options. Your results will be listed from the lowest price, so you’ll see the cheapest nonstop airfares first. You can also check out prices for nearby days by clicking “Flexible dates” located near the top of the page.
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.
$394.34
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