What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Simpson Bay flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 36% of flights being delayed.

How often are flights from Chicago to Simpson Bay delayed?

About 37% of weekly flights between Chicago and Simpson Bay have experienced delays in the past year, with the average delay time being 129 minutes.

What is the most punctual flight time for Chicago to Simpson Bay flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

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

For as low as $259, Spirit Airlines can have you in Simpson Bay from Chicago O'Hare Intl Airport in 6h 55m. 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 $315, 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 54% 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 $522, our data shows the cheapest flight currently is $291. When looking at the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana), you can expect to pay $259 for that flight.

What are the most popular airlines that fly from Chicago O'Hare Intl Airport to Simpson Bay?

Before booking your flight from Chicago O'Hare Intl Airport to Simpson Bay check out the most popular airlines for this route: American Airlines, United Airlines or Spirit Airlines.

Most accurate provider : When it comes to deals on Chicago O'Hare Intl Airport-Simpson Bay flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Chicago O'Hare Intl Airport-Simpson Bay flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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.

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.

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.

$94+ Flights from Chicago O'Hare Intl Airport to Simpson Bay

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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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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

Most accurate provider	CheapOair 3 stars
Most trusted provider	CheapOair 3 stars
Round-trip from	$259 (Super.com)
One-way from	$94 (Cheapflightsfares)
Popular in	March
Cheapest in	September
Average price	$674
Good round-trip deal	$542 or less
Good one-way deal	$313 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

Search Deals

Highest demand for flights based on searches. 15% potential increase in price ($126 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average RT price).

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Average for round-trip flights in November 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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Price to beat on a one-way 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 November 29, 2025.

Mon 12/155:00 amORD - SXM

1 stop7h 15mSpirit Airlines

Mon 12/223:20 pmSXM - ORD

1 stop11h 10mSpirit Airlines

Deal found 11/27

$291

Sun 12/149:14 pmORD - SXM

2 stops15h 01mSpirit Airlines

Sat 12/203:20 pmSXM - ORD

1 stop11h 10mSpirit Airlines

Deal found 11/29

$326

Thu 12/1812:39 pmORD - SXM

2 stops23h 36mMultiple Airlines

Mon 12/223:20 pmSXM - ORD

1 stop11h 10mMultiple Airlines

Deal found 11/28

$333

Mon 12/152:00 pmORD - SXM

2 stops22h 40mMultiple Airlines

Mon 12/223:20 pmSXM - ORD

1 stop11h 10mMultiple Airlines

Deal found 11/27

$341

Mon 12/85:00 amORD - SXM

1 stop7h 15mSpirit Airlines

Fri 12/123:20 pmSXM - ORD

1 stop10h 49mSpirit Airlines

Deal found 11/28

$348

Tue 12/237:01 pmORD - SXM

2 stops17h 14mMultiple Airlines

Sat 12/273:20 pmSXM - ORD

1 stop11h 10mMultiple Airlines

Deal found 11/27

$367

Thu 12/183:26 pmORD - SXM

1 stop20h 49mSpirit Airlines

Mon 12/223:20 pmSXM - ORD

1 stop11h 10mSpirit Airlines

Deal found 11/28

$372

Wed 12/245:00 amORD - SXM

1 stop7h 15mSpirit Airlines

Mon 12/293:20 pmSXM - ORD

1 stop11h 10mSpirit Airlines

Deal found 11/29

$379

Best flights from O'Hare Intl to Simpson Bay
Discover carefully curated flight deals from O'Hare Intl to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 29, 2025.

Sun 1/255:15 amORD - SXM

1 stop6h 59mSpirit Airlines

Thu 1/293:09 pmSXM - ORD

1 stop10h 37mSpirit Airlines

Deal found 11/26

$300

Fri 1/164:41 pmORD - SXM

2 stops19h 33mMultiple Airlines

Mon 1/193:15 pmSXM - ORD

1 stop22h 07mMultiple Airlines

Deal found 11/28

$344

Thu 12/118:00 amORD - SXM

1 stop30h 00mAir Canada

Tue 12/163:40 pmSXM - ORD

1 stop30h 30mAir Canada

Deal found 11/28

$411

Sun 1/255:59 pmORD - SXM

2 stops16h 31mDelta

Thu 1/291:55 pmSXM - ORD

1 stop12h 01mDelta

Deal found 11/26

$506

Wed 1/145:32 pmORD - SXM

1 stop18h 42mSpirit Airlines

Sun 1/183:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Deal found 11/27

$343

Sat 1/1010:48 amORD - SXM

3 stops25h 22mSpirit Airlines

Sat 1/173:15 pmSXM - ORD

3 stops28h 37mSpirit Airlines

Deal found 11/29

$423

Fri 2/136:00 pmORD - SXM

1 stop19h 20mMultiple Airlines

Sat 2/213:15 pmSXM - ORD

1 stop11h 03mMultiple Airlines

Deal found 11/28

$496

Sun 3/298:20 pmORD - SXM

2 stops40h 15mAir Canada

Sun 4/52:40 pmSXM - ORD

2 stops23h 20mAir Canada

Deal found 11/26

$502

Fri 1/2312:44 pmORD - SXM

3 stops23h 26mSpirit Airlines

Sat 1/313:15 pmSXM - ORD

3 stops25h 02mSpirit Airlines

Deal found 11/27

$427

Sun 12/217:57 pmORD - SXM

2 stops16h 18mSpirit Airlines

Sat 12/273:20 pmSXM - ORD

1 stop11h 10mSpirit Airlines

Deal found 11/27

$460

Last-minute flights from O'Hare Intl to Simpson Bay
Discover last-minute flight deals from O'Hare Intl to Simpson Bay. Data last updated November 29, 2025 and is based on user searches.

Mon 12/85:00 amORD - SXM

1 stop7h 15mSpirit Airlines

Fri 12/123:20 pmSXM - ORD

1 stop10h 49mSpirit Airlines

Deal found 11/28

$348

Sun 12/149:14 pmORD - SXM

2 stops15h 01mSpirit Airlines

Sat 12/203:20 pmSXM - ORD

1 stop11h 10mSpirit Airlines

Deal found 11/29

$326

Mon 12/155:00 amORD - SXM

1 stop7h 15mSpirit Airlines

Mon 12/223:20 pmSXM - ORD

1 stop11h 10mSpirit Airlines

Deal found 11/27

$291

Mon 12/152:00 pmORD - SXM

2 stops22h 40mMultiple Airlines

Mon 12/223:20 pmSXM - ORD

1 stop11h 10mMultiple Airlines

Deal found 11/27

$341

Thu 12/1812:39 pmORD - SXM

2 stops23h 36mMultiple Airlines

Mon 12/223:20 pmSXM - ORD

1 stop11h 10mMultiple Airlines

Deal found 11/28

$333

Thu 12/183:26 pmORD - SXM

1 stop20h 49mSpirit Airlines

Mon 12/223:20 pmSXM - ORD

1 stop11h 10mSpirit Airlines

Deal found 11/28

$372

Tue 12/237:01 pmORD - SXM

2 stops17h 14mMultiple Airlines

Sat 12/273:20 pmSXM - ORD

1 stop11h 10mMultiple Airlines

Deal found 11/27

$367

Wed 12/245:00 amORD - SXM

1 stop7h 15mSpirit Airlines

Mon 12/293:20 pmSXM - ORD

1 stop11h 10mSpirit Airlines

Deal found 11/29

$379

One-way flights from O'Hare Intl to Simpson Bay
Search for one-way flight options from O'Hare Intl to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated November 29, 2025.

Mon 1/265:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 11/27

$94

Sat 2/287:59 pmORD - SXM

1 stop16h 11mSpirit Airlines

Deal found 11/29

$104

Thu 1/292:52 pmORD - SXM

1 stop21h 22mMultiple Airlines

Deal found 11/28

$105

Wed 1/285:32 pmORD - SXM

1 stop18h 42mSpirit Airlines

Deal found 11/28

$106

Sat 1/175:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 11/27

$110

Thu 2/265:15 amORD - SXM

1 stop7h 01mSpirit Airlines

Deal found 11/29

$111

Thu 2/2611:42 amORD - SXM

1 stop24h 28mMultiple Airlines

Deal found 11/29

$128

Sun 1/2512:21 pmORD - SXM

2 stops23h 53mMultiple Airlines

Deal found 11/27

$130

Fri 1/306:05 amORD - SXM

2 stops30h 05mMultiple Airlines

Deal found 11/28

$131

Cheapflights Fare Finder

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

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/25

5:15 am-2:14 pm

1 stop6h 59m

Simpson Bay Princess Juliana

Thu 1/29

3:09 pm-11:46 pm

1 stop10h 37m

$300

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 1/14

5:32 pm-2:14 pm

1 stop18h 42m

Simpson Bay Princess Juliana

Sun 1/18

3:15 pm-11:46 pm

1 stop10h 31m

$343

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/16

4:41 pm-2:14 pm

2 stops19h 33m

Simpson Bay Princess Juliana

Mon 1/19

3:15 pm-11:22 am

1 stop22h 07m

$344

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/11

8:00 am-4:00 pm

1 stop30h 00m

Simpson Bay Princess Juliana

Tue 12/16

3:40 pm-8:10 pm

1 stop30h 30m

$411

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/10

10:48 am-2:10 pm

3 stops25h 22m

Simpson Bay Princess Juliana

Sat 1/17

3:15 pm-5:52 pm

3 stops28h 37m

$423

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/23

12:44 pm-2:10 pm

3 stops23h 26m

Simpson Bay Princess Juliana

Sat 1/31

3:15 pm-2:17 pm

3 stops25h 02m

$427

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 12/21

7:57 pm-2:15 pm

2 stops16h 18m

Simpson Bay Princess Juliana

Sat 12/27

3:20 pm-12:30 am

1 stop11h 10m

$460

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 2/13

6:00 pm-3:20 pm

1 stop19h 20m

Simpson Bay Princess Juliana

Sat 2/21

3:15 pm-12:18 am

1 stop11h 03m

$496

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/29

8:20 pm-1:35 pm

2 stops40h 15m

Simpson Bay Princess Juliana

Sun 4/5

2:40 pm-1:00 pm

2 stops23h 20m

$502

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/25

5:59 pm-12:30 pm

2 stops16h 31m

Simpson Bay Princess Juliana

Thu 1/29

1:55 pm-11:56 pm

1 stop12h 01m

$506

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/27

Showing 1-10 of 20 results

Compare providers for flights from O'Hare Intl to Simpson Bay

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 November.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust Score*3 stars
JustAirTicket	Price Accuracy-	Trust Score*1 star
CheapOair	Price Accuracy3 stars	Trust Score*3 stars
AranGrant	Price Accuracy2 stars	Trust Score*3 stars
CheapTicketsDeal	Price Accuracy3 stars	Trust 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 CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Chicago O'Hare Intl Airport-Simpson Bay flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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

Prices

Delays

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

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?

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 51% on the cost of your flight, compared to a flight in the morning.

Reviews of airlines servicing Simpson Bay

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

8,011 reviews

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

8,011 reviews

Delta

7.9

Good

8,011 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

United Airlines

7.4

Good

9,057 reviews

Delta

7.9

Good

8,011 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

American Airlines

7.2

Good

11,042 reviews

Delta

7.9

Good

8,011 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

JetBlue

7.2

Good

2,904 reviews

Delta

7.9

Good

8,011 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

Spirit Airlines

6.3

Okay

8,160 reviews

Delta

7.9

Good

8,011 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

Related info for your journey

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 $259, Spirit Airlines can have you in Simpson Bay from Chicago O'Hare Intl Airport in 6h 55m. 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 $315, 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 54% 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 $522, our data shows the cheapest flight currently is $291. When looking at the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana), you can expect to pay $259 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

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

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$315	Average$399	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$318	Average$774	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$420	Average$878	FlexibilityNo cancel fee	On-time69%
JetBlue	Cheapest$535	Average$711	FlexibilityNo cancel fee	On-time62%
American Airlines	Cheapest$550	Average$702	FlexibilityNo cancel fee	On-time71%

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$94+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from O'Hare Intl to Simpson Bay with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from O'Hare Intl to Simpson Bay

Cheapest flights from O'Hare Intl to Simpson BayExplore 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 November 29, 2025.

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 November 29, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Simpson Bay that are best for you.

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 November.

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.

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?

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

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

How often are flights from Chicago to Simpson Bay delayed?

What is the most punctual flight time for Chicago to Simpson Bay flights?

What day of the week experiences the fewest flight delays on this route?

Which airline has the best punctuality record on Chicago to Simpson Bay flights?

Reviews of airlines servicing Simpson Bay

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?

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

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

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

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

How can I 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?

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

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Alternative routes for O'Hare Intl to Simpson Bay

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

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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 November 29, 2025.