$207 Cheap Flights from Philipsburg (SXM) to Chicago (ORD)

View $207 flight on Fri, May 23, 2025Opens in a new window

Popular airlines from Princess Juliana Intl. Airport (SXM) to Chicago O'Hare Intl. Airport (ORD)

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Find available prices by choosing your travel dates.

Cheap Flights from Philipsburg to Chicago (SXM-ORD)

Prices were available within the past 7 days and start at $207 for one-way flights and $366 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Fri, May 23 - Fri, May 30
SXM
Saint Martin
ORD
Chicago
$366 Roundtrip, found 1 hour ago
$366
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Fri, May 23 from Saint Martin to Chicago, returning Fri, May 30, priced at $366 found 1 hour ago
Spirit Airlines
Fri, May 23 - Fri, May 30
SXM
Saint Martin
ORD
Chicago
$386 Roundtrip, found 1 hour ago
$386
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Fri, May 23 from Saint Martin to Chicago, returning Fri, May 30, priced at $386 found 1 hour ago
Spirit Airlines
Sat, May 17 - Fri, May 23
SXM
Saint Martin
ORD
Chicago
$397 Roundtrip, found 4 days ago
$397
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, May 17 from Saint Martin to Chicago, returning Fri, May 23, priced at $397 found 4 days ago
Spirit Airlines
Fri, May 30 - Mon, Jun 2
SXM
Saint Martin
ORD
Chicago
$402 Roundtrip, found 1 day ago
$402
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, May 30 from Saint Martin to Chicago, returning Mon, Jun 2, priced at $402 found 1 day ago
Frontier Airlines
Sat, May 24 - Fri, Jun 6
SXM
Saint Martin
ORD
Chicago
$403 Roundtrip, found 2 days ago
$403
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 24 from Saint Martin to Chicago, returning Fri, Jun 6, priced at $403 found 2 days ago
Spirit Airlines
Fri, May 23 - Fri, May 30
SXM
Saint Martin
ORD
Chicago
$407 Roundtrip, found 1 hour ago
$407
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Fri, May 23 from Saint Martin to Chicago, returning Fri, May 30, priced at $407 found 1 hour ago
Spirit Airlines
Fri, Jun 6 - Fri, Jun 13
SXM
Saint Martin
ORD
Chicago
$408 Roundtrip, found 5 days ago
$408
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Fri, Jun 6 from Saint Martin to Chicago, returning Fri, Jun 13, priced at $408 found 5 days ago
JetBlue Airways
Wed, May 14 - Sat, May 17
SXM
Saint Martin
ORD
Chicago
$464 Roundtrip, found 5 days ago
$464
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, May 14 from Saint Martin to Chicago, returning Sat, May 17, priced at $464 found 5 days ago
American Airlines
Wed, Jun 18 - Wed, Jun 25
SXM
Saint Martin
ORD
Chicago
$622 Roundtrip, found 1 hour ago
$622
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Jun 18 from Saint Martin to Chicago, returning Wed, Jun 25, priced at $622 found 1 hour ago
Delta
Wed, Jun 18 - Wed, Jun 25
SXM
Saint Martin
ORD
Chicago
$622 Roundtrip, found 1 hour ago
$622
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Jun 18 from Saint Martin to Chicago, returning Wed, Jun 25, priced at $622 found 1 hour ago

Frequently asked questions

How much does a flight from Princess Juliana Intl. Airport (SXM) to O'Hare Intl. Airport (ORD) cost?
Discover the latest flight deals from SXM to ORD by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from SXM to ORD?
The cheapest flights from SXM to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Princess Juliana Intl. Airport (SXM) to O'Hare Intl. Airport (ORD)?
Take a nonstop flight with United Airlines and head straight from Princess Juliana Intl. Airport (SXM) to O’Hare Intl. Airport (ORD).
What is the cheapest airline that flies from SXM to ORD?
At the moment, the cheapest airline offering one-way flights from SXM to ORD is United. You can jet off on this route from $537. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from SXM on April 26 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from Princess Juliana Intl. Airport (SXM) to O'Hare Intl. Airport (ORD)?
On average, Princess Juliana Intl. Airport (SXM) has 2 nonstop flights to O’Hare Intl. Airport (ORD) every week. If you’re looking for more choice, take advantage of Expedia’s filters to look for flights with one or two stops. Squeeze in a visit to another destination or simply break up your journey.
What are the most popular departure times for flights from Princess Juliana Intl. Airport (SXM) to O'Hare Intl. Airport (ORD)?
Flights between SXM and ORD tend to be busiest at 2 PM. If you want a more relaxed atmosphere and potentially cheaper tickets, choose a departure that’s outside typical rush times.
What day of the week has the most flights from SXM to ORD?
If you jet off on a Saturday, you’ll get the greatest range of choices for flights from Princess Juliana Intl. Airport (SXM) to O’Hare Intl. Airport (ORD).
What is the earliest flight from Princess Juliana Intl. Airport (SXM) to O'Hare Intl. Airport (ORD)?
Princess Juliana Intl. Airport (SXM)’s earliest flight to O’Hare Intl. Airport (ORD) departs at approximately 2:46PM UTC-4. With a travel time of 5h 54m, you’ll land at around 6:40PM UTC-6.
How long does it take to fly from Princess Juliana Intl. Airport (SXM) to O'Hare Intl. Airport (ORD)?
Flights from SXM to ORD have an average travel time of 5 hours and 54 minutes. The distance between these two airports is 2,200 mi.
What is the best time to fly from Princess Juliana Intl. Airport (SXM) to O'Hare Intl. Airport (ORD)?
To avoid possible delays on the Princess Juliana Intl. Airport (SXM) to O’Hare Intl. Airport (ORD) route, aim to travel before 3 PM. Later departures have a 22% higher chance of being canceled.**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)?
If you’ve booked a direct flight from Princess Juliana Intl. Airport (SXM) to Chicago, O’Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Princess Juliana Intl. Airport (SXM) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from SXM to ORD are generally more expensive. For the cheapest rates, start searching for flights well ahead of time. That said, if you’re flexible with your travel dates, you may score a cheap ticket right before your journey.
Is it cheaper to book a SXM to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a SXM to ORD flight and hotel package with Expedia could lead to significant savings. What’s more, managing everything in one place will take the stress out of planning your trip. Just pick your flights and choose from our wide range of hotels, then customize your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Princess Juliana Intl. Airport (SXM) to O'Hare Intl. Airport (ORD)?
It’s usually possible to reschedule or cancel your SXM to ORD flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline’s policies in your itinerary to see what changes are allowed and whether any costs are involved. You’ll also find more details on our Customer Service portal.
*Available to One Key members.