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Simpson Bay

$142+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 August, booked 17 days in advance, depart on a Monday or Thursday and return on a Monday

Cheap 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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$317
(Copa Airlines)

One-way from

$142
(Priceline)

Popular in

March

Cheapest in

September

Average price

$637

Good round-trip deal

$584 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Simpson Bay Princess Juliana flights.
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From Chicago O'Hare Intl to Simpson Bay Princess Juliana
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One-way flight from Chicago O'Hare Intl to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 14% potential increase in price ($125 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Simpson Bay Princess Juliana.
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Find 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 October 14, 2025.

This Frontier deal was found by Cheapflights users on 10/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:10 amORD - SXM
1 stop8h 10mFrontier
Sat 12/134:30 pmSXM - ORD
1 stop9h 38mFrontier
Deal found 10/13$365
This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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 11/85:10 amORD - SXM
1 stop7h 05mSpirit Airlines
Fri 11/143:20 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Deal found 10/12$370
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Tue 12/93:21 pmORD - SXM
1 stop20h 49mSpirit Airlines
Wed 12/173:15 pmSXM - ORD
1 stop10h 19mSpirit Airlines
Deal found 10/12$374
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:53 pmORD - SXM
1 stop16h 35mDelta
Wed 12/173:53 pmSXM - ORD
1 stop8h 50mDelta
Deal found 10/13$375
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:53 pmORD - SXM
1 stop16h 35mDelta
Thu 12/184:15 pmSXM - ORD
2 stops26h 33mDelta
Deal found 10/13$380
This American Airlines deal was found by Cheapflights users on 10/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/137:07 pmORD - SXM
1 stop19h 18mAmerican Airlines
Fri 12/191:39 pmSXM - ORD
1 stop13h 54mAmerican Airlines
Deal found 10/12$385
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 12/107:41 pmORD - SXM
2 stops37h 47mMultiple Airlines
Wed 12/173:15 pmSXM - ORD
1 stop10h 19mMultiple Airlines
Deal found 10/12$388
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Tue 12/97:00 amORD - SXM
2 stops26h 28mMultiple Airlines
Wed 12/173:15 pmSXM - ORD
1 stop10h 19mMultiple Airlines
Deal found 10/12$389
This American Airlines deal was found by Cheapflights users on 10/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:39 pmORD - SXM
1 stop17h 19mAmerican Airlines
Sat 12/203:04 pmSXM - ORD
Nonstop5h 54mAmerican Airlines
Deal found 10/13$390
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Sun 11/910:52 amORD - SXM
1 stop25h 23mSpirit Airlines
Fri 11/143:20 pmSXM - ORD
1 stop21h 52mSpirit Airlines
Deal found 10/12$392
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:30 pmORD - SXM
1 stop17h 30mDelta
Fri 12/191:45 pmSXM - ORD
1 stop10h 58mDelta
Deal found 10/13$400

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 October 14, 2025.
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

Mon 2/23

6:10 pm-12:15 pm

1 stop16h 05m

Simpson Bay Princess Juliana

Fri 2/27

4:26 pm-10:09 am

1 stop19h 43m

$329

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/25

6:05 am-3:51 pm

1 stop7h 46m

Simpson Bay Princess Juliana

Thu 1/29

2:52 pm-10:59 pm

1 stop10h 07m

$329

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/22

5:50 am-2:56 pm

1 stop7h 06m

Simpson Bay Princess Juliana

Thu 2/26

4:26 pm-10:09 am

1 stop19h 43m

$329

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 1/12

3:50 pm-12:15 pm

2 stops18h 25m

Simpson Bay Princess Juliana

Fri 1/16

4:26 pm-12:41 pm

2 stops22h 15m

$334

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/22

6:10 pm-12:15 pm

1 stop16h 05m

Simpson Bay Princess Juliana

Fri 2/27

4:26 pm-1:23 pm

2 stops22h 57m

$334

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/24

2:13 pm-11:24 am

1 stop19h 11m

Simpson Bay Princess Juliana

Mon 2/2

12:25 pm-12:04 am

1 stop13h 39m

$347

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/9

6:10 pm-12:15 pm

1 stop16h 05m

Simpson Bay Princess Juliana

Thu 1/15

4:26 pm-10:09 am

1 stop19h 43m

$354

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 12/8

7:53 pm-2:28 pm

1 stop16h 35m

Simpson Bay Princess Juliana

Fri 12/19

1:45 pm-10:43 pm

1 stop10h 58m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 11/24

5:23 am-2:55 pm

1 stop7h 32m

Simpson Bay Princess Juliana

Thu 11/27

4:20 pm-10:30 pm

1 stop8h 10m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/17

7:50 pm-1:45 pm

1 stop15h 55m

Simpson Bay Princess Juliana

Sat 1/24

2:03 pm-11:09 pm

1 stop11h 06m

$379

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 20 results
1
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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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
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 October 10, 2025.

The best time to book flights from Chicago O'Hare Intl Airport to Simpson Bay is 17 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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Simpson Bay (average of $312). Flying from Chicago O'Hare Intl Airport to Simpson Bay in June is currently the most expensive (average of $595). 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 October 14, 2025.

It’s optimal to fly from Chicago O'Hare Intl Airport to Simpson Bay at noon. By choosing this option you can save up to 52% on the cost of your flight, compared to a flight in the morning.

How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Simpson Bay?

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 October 14, 2025.
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
8.0
Very good
7,975 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
8.0
Very good
7,975 reviews
Delta
8.0
Very good
7,975 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,976 reviews
Delta
8.0
Very good
7,975 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,042 reviews
Delta
8.0
Very good
7,975 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Spirit Airlines
6.3
Okay
8,096 reviews
Delta
8.0
Very good
7,975 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 4 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 $329, Delta can have you in Simpson Bay from Chicago O'Hare Intl Airport in 7h 46m. There are 2204 mi between Chicago O'Hare Intl Airport and Simpson Bay. This flight may include one or multiple stops.

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

    Spirit Airlines, at $316, 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 55% 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 $713, our data shows the cheapest flight currently is $480. When looking at the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana), you can expect to pay $329 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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Simpson Bay (average of $312). Flying from Chicago O'Hare Intl Airport to Simpson Bay in June is currently the most expensive (average of $595). 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

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Midway to Simpson Bay flights

Top 4 airlines flying from O'Hare Intl to Simpson Bay

Discover the top 4 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$318Average$806FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$597Average$929FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$618Average$713FlexibilityNo cancel feeOn-time71%

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