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Simpson Bay

$72+ Cheap flights from O'Hare Intl (ORD) to Simpson Bay (SXM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Mar 16 — Mar 231
Mon 3/16
Mon 3/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Simpson Bay Princess Juliana are usually found in September or February, booked 19 days in advance, depart on a Tuesday or Monday and return on a Monday

Cheap flight deals from O'Hare Intl to Simpson Bay

Cheapest flights from O'Hare Intl to Simpson Bay
Explore the most affordable flight options available from O'Hare Intl to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 14, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Sat 3/73:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/10$237
This Priceline deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/88:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Wed 3/112:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/11$238
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/175:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Thu 2/193:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/10$268
This Cheapflightsfares deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Thu 3/122:20 pm
SXM
-
ORD
1 stop9h 57m
Spirit Airlines
Deal found 2/11$269
This Super.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Thu 3/122:20 pm
SXM
-
ORD
1 stop9h 57m
Spirit Airlines
Deal found 2/11$272
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:19 am
ORD
-
SXM
2 stops25h 56m
Spirit Airlines
Sat 3/73:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/10$277
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Tue 3/33:20 pm
SXM
-
ORD
1 stop22h 02m
Spirit Airlines
Deal found 2/11$285
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Tue 3/33:20 pm
SXM
-
ORD
1 stop22h 02m
Spirit Airlines
Deal found 2/11$286
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:15 am
ORD
-
SXM
1 stop7h 00m
Multiple Airlines
Mon 3/92:20 pm
SXM
-
ORD
1 stop21h 16m
Multiple Airlines
Deal found 2/11$287
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/185:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Wed 2/253:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/10$289

Find flight deals from O'Hare Intl to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Cheapflightsfares)

One-way from

$72
(Cheapflightsfares)

Popular in

May

Cheapest in

September

Average price

$578

Good round-trip deal

$612 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Simpson Bay Princess Juliana flights.
Search Deals
From Chicago O'Hare Intl to Simpson Bay Princess Juliana
Search Deals
One-way flight from Chicago O'Hare Intl to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Simpson Bay Princess Juliana.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 14, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Simpson Bay that are best for you.

Fly from

O'Hare Intl

Fly to

Simpson Bay

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 3/5

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Sat 3/7

3:20 pm-11:47 pm

1 stop10h 27m

$288

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/1

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Tue 3/10

2:20 pm-11:47 pm

1 stop10h 27m

$290

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/4

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Mon 3/9

2:20 pm-11:47 pm

1 stop10h 27m

$292

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/4

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sat 3/7

3:20 pm-11:47 pm

1 stop10h 27m

$304

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 3/10

8:16 pm-1:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Tue 3/17

2:20 pm-11:17 pm

1 stop9h 57m

$305

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 4/10

5:05 am-1:30 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Wed 4/15

2:11 pm-11:41 pm

1 stop10h 30m

$308

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 3/5

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Mon 3/9

2:20 pm-11:47 pm

1 stop10h 27m

$324

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 4/29

5:05 am-1:16 pm

1 stop7h 11m

Simpson Bay Princess Juliana

Mon 5/4

2:35 pm-9:17 pm

1 stop31h 42m

$338

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 3/2

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Tue 3/10

2:20 pm-8:23 am

2 stops19h 03m

$340

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/28

10:44 am-2:15 pm

2 stops25h 31m

Simpson Bay Princess Juliana

Sat 3/7

3:20 pm-11:47 pm

1 stop10h 27m

$341

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Showing 1-10 of 22 results
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Compare providers for flights from O'Hare Intl to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Simpson Bay in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from O'Hare Intl to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Simpson Bay

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Simpson Bay?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Simpson Bay. Price data was last updated on February 6, 2026.

The best time to book flights from Chicago O'Hare Intl Airport to Simpson Bay is 18 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Simpson Bay?

Currently, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Simpson Bay (average of $231). Flying from Chicago O'Hare Intl Airport to Simpson Bay in June is currently the most expensive (average of $597). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to SXM?

Find hourly flight availability from O'Hare Intl to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 14, 2026.

When flying from Chicago O'Hare Intl Airport to Simpson Bay, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated February 14, 2026.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Chicago O'Hare Intl Airport to Simpson Bay to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,203 reviews

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,203 reviews
Delta
7.9
Good
8,203 reviews

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,289 reviews
Delta
7.9
Good
8,203 reviews

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,288 reviews
Delta
7.9
Good
8,203 reviews

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,898 reviews
Delta
7.9
Good
8,203 reviews

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,451 reviews
Delta
7.9
Good
8,203 reviews

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Simpson Bay from Chicago O'Hare Intl?

    Simpson Bay Princess Juliana (SXM) is the airport you will fly into if you book a flight from Chicago O'Hare Intl to Simpson Bay. You should not have trouble finding flights to Princess Juliana from Chicago O'Hare Intl; the airport handles an average of 0 inbound flights from Chicago O'Hare Intl per day. You should also have plenty of airline options to choose from since 5 airlines have flights to the Simpson Bay airport from Chicago O'Hare Intl. It is only a 0.5 mi journey from Princess Juliana (SXM) to Simpson Bay’s city center.

  • How long is the flight from Chicago O'Hare Intl Airport to Simpson Bay?

    For as low as $288, Spirit Airlines can have you in Simpson Bay from Chicago O'Hare Intl Airport in 15h 59m. There are 2204 mi between Chicago O'Hare Intl Airport and Simpson Bay.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Simpson Bay round-trip?

    Spirit Airlines, at $231, was found to be the cheapest airline from Chicago O'Hare Intl Airport to Simpson Bay.Alternate airlines to your destination round-trip include Delta and United Airlines. These flights start at 63% lower than the current average price 3 months from now.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Simpson Bay?

    While on average a flight from Chicago O'Hare Intl Airport to Simpson Bay is generally $726, our data shows the cheapest flight currently is $554. When looking at the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana), you can expect to pay $286 for that flight.

  • Can I find deals for flights from O'Hare Intl to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Simpson Bay.

  • Can I find deals for business class flights from O'Hare Intl to Simpson Bay?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Simpson Bay?

    Currently, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Simpson Bay (average of $231). Flying from Chicago O'Hare Intl Airport to Simpson Bay in June is currently the most expensive (average of $597). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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Alternative routes for O'Hare Intl to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
Midway to Simpson Bay flights

Top 5 airlines flying from O'Hare Intl to Simpson Bay

Discover the top 5 airlines that operate flights from O'Hare Intl to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$231Average$393FlexibilityNo cancel feeOn-time65%
DeltaCheapest$290Average$408FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$410Average$752FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$501Average$681FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$568Average$731FlexibilityNo cancel feeOn-time62%

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