How often are flights from Chicago to Simpson Bay delayed?

About 34% of weekly flights between Chicago and Simpson Bay have experienced delays in the past year, with the average delay time being 129 minutes.

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 33% of flights being delayed.

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

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

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 $231, 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?

Delta, at $292, was found to be the cheapest airline from Chicago O'Hare Intl Airport to Simpson Bay.Alternate airlines to your destination round-trip include Spirit Airlines and United Airlines. These flights start at 57% 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 $503, 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 $230 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.

$77+ Flights from Chicago O'Hare Intl Airport to Simpson Bay

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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

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 December 12, 2025.

Wed 12/315:00 amORD - SXM

1 stop7h 15mSpirit Airlines

Fri 1/93:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Deal found 12/10

$343

Sun 12/141:52 pmORD - SXM

2 stops22h 23mSpirit Airlines

Sat 12/203:20 pmSXM - ORD

1 stop11h 10mSpirit Airlines

Deal found 12/10

$442

Mon 12/225:00 amORD - SXM

1 stop7h 15mMultiple Airlines

Mon 12/293:20 pmSXM - ORD

2 stops29h 13mMultiple Airlines

Deal found 12/11

$488

Tue 12/2312:32 pmORD - SXM

2 stops23h 43mMultiple Airlines

Fri 12/263:20 pmSXM - ORD

1 stop11h 10mMultiple Airlines

Deal found 12/10

$493

Mon 12/225:00 amORD - SXM

1 stop7h 15mSpirit Airlines

Wed 12/313:20 pmSXM - ORD

1 stop21h 54mSpirit Airlines

Deal found 12/11

$497

Sun 12/217:59 pmORD - SXM

1 stop16h 51mDelta

Wed 12/311:45 pmSXM - ORD

1 stop12h 17mDelta

Deal found 12/11

$501

Thu 12/255:25 amORD - SXM

2 stops30h 50mMultiple Airlines

Wed 12/313:20 pmSXM - ORD

1 stop21h 54mMultiple Airlines

Deal found 12/11

$514

Sun 12/145:00 amORD - SXM

1 stop6h 58mAmerican Airlines

Sat 12/203:04 pmSXM - ORD

Nonstop5h 54mAmerican Airlines

Deal found 12/10

$518

Sun 12/217:30 amORD - SXM

1 stop28h 45mMultiple Airlines

Mon 12/293:20 pmSXM - ORD

2 stops29h 13mMultiple Airlines

Deal found 12/11

$520

Mon 12/295:00 amORD - SXM

1 stop7h 15mMultiple Airlines

Tue 1/62:30 pmSXM - ORD

1 stop29h 13mMultiple Airlines

Deal found 12/9

$522

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 December 12, 2025.

Mon 2/95:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Wed 2/183:15 pmSXM - ORD

1 stop11h 03mSpirit Airlines

Deal found 12/10

$231

Sun 2/15:15 amORD - SXM

1 stop6h 55mMultiple Airlines

Sun 2/15:36 pmSXM - ORD

2 stops26h 07mMultiple Airlines

Deal found 12/10

$336

Sat 3/75:05 amORD - SXM

1 stop8h 35mFrontier

Sat 3/143:40 pmSXM - ORD

1 stop9h 21mFrontier

Deal found 12/10

$446

Sun 1/2510:07 amORD - SXM

2 stops26h 03mSpirit Airlines

Fri 1/303:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Deal found 12/10

$350

Wed 2/113:35 pmORD - SXM

1 stop21h 05mMultiple Airlines

Wed 2/183:15 pmSXM - ORD

1 stop11h 03mMultiple Airlines

Deal found 12/10

$360

Sat 1/245:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Mon 2/23:15 pmSXM - ORD

2 stops19h 57mSpirit Airlines

Deal found 12/10

$399

Tue 2/109:23 amORD - SXM

2 stops21h 07mMultiple Airlines

Tue 2/173:15 pmSXM - ORD

1 stop22h 12mMultiple Airlines

Deal found 12/10

$448

Thu 1/1510:07 amORD - SXM

2 stops26h 03mSpirit Airlines

Sun 1/183:15 pmSXM - ORD

2 stops19h 57mSpirit Airlines

Deal found 12/11

$421

Sat 1/245:52 pmORD - SXM

1 stop18h 48mMultiple Airlines

Sun 2/15:36 pmSXM - ORD

1 stop28h 00mMultiple Airlines

Deal found 12/10

$455

Thu 1/297:45 amORD - SXM

2 stops30h 36mMultiple Airlines

Mon 2/25:00 pmSXM - ORD

2 stops20h 06mMultiple Airlines

Deal found 12/11

$466

Mon 3/307:41 pmORD - SXM

1 stop16h 27mMultiple Airlines

Fri 4/34:00 pmSXM - ORD

1 stop24h 48mMultiple Airlines

Deal found 12/11

$472

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 December 12, 2025 and is based on user searches.

Sat 1/35:00 amORD - SXM

1 stop7h 15mSpirit Airlines

Fri 1/93:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Deal found 12/10

$251

Thu 1/88:43 pmORD - SXM

1 stop15h 27mSpirit Airlines

Thu 1/153:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Deal found 12/10

$230

Thu 1/158:43 pmORD - SXM

1 stop15h 27mSpirit Airlines

Sun 1/183:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Deal found 12/9

$271

Sun 1/185:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Sun 1/253:15 pmSXM - ORD

1 stop30h 23mSpirit Airlines

Deal found 12/11

$265

Fri 1/238:43 pmORD - SXM

1 stop15h 27mSpirit Airlines

Sat 1/313:15 pmSXM - ORD

1 stop8h 48mSpirit Airlines

Deal found 12/11

$231

Sat 1/245:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Sat 1/313:15 pmSXM - ORD

1 stop8h 48mSpirit Airlines

Deal found 12/11

$253

Sat 1/245:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Mon 2/23:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Deal found 12/11

$262

Sun 1/255:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Fri 1/303:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Deal found 12/10

$254

Mon 1/265:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Mon 2/23:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Deal found 12/11

$241

Thu 1/298:43 pmORD - SXM

1 stop15h 27mSpirit Airlines

Mon 2/23:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Deal found 12/11

$239

Fri 1/305:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Mon 2/23:15 pmSXM - ORD

1 stop10h 31mSpirit Airlines

Deal found 12/11

$260

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 December 12, 2025.

Mon 2/95:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/10

$77

Thu 2/265:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/11

$78

Wed 1/75:00 amORD - SXM

1 stop7h 15mSpirit Airlines

Deal found 12/10

$83

Sun 2/83:00 pmORD - SXM

1 stop21h 10mMultiple Airlines

Deal found 12/10

$95

Fri 1/305:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/9

$98

Wed 3/45:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/9

$99

Sat 1/175:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/9

$101

Sat 1/105:50 amORD - SXM

1 stop7h 16mFrontier

Deal found 12/10

$103

Thu 1/88:43 pmORD - SXM

1 stop15h 27mSpirit Airlines

Deal found 12/11

$104

Sun 3/15:15 amORD - SXM

1 stop6h 55mSpirit Airlines

Deal found 12/9

$106

Find flight deals from O'Hare Intl to Simpson Bay

Most accurate provider	CheapOair 3 stars
Most trusted provider	CheapOair 3 stars
Round-trip from	$230 (Super.com)
One-way from	$77 (Super.com)
Popular in	March
Cheapest in	September
Average price	$735
Good round-trip deal	$556 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.

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. 14% potential increase in price ($117 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Price to beat on a round-trip flight from Chicago O'Hare Intl to Simpson Bay Princess Juliana.

Search Deals

Price to beat on a one-way flight from Chicago O'Hare Intl to Simpson Bay Princess Juliana.

Search Deals

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

Mon 2/9

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Wed 2/18

3:15 pm-12:18 am

1 stop11h 03m

$231

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/1

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sun 2/1

5:36 pm-5:43 pm

2 stops26h 07m

$336

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/25

10:07 am-2:10 pm

2 stops26h 03m

Simpson Bay Princess Juliana

Fri 1/30

3:15 pm-11:46 pm

1 stop10h 31m

$350

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 2/11

3:35 pm-2:40 pm

1 stop21h 05m

Simpson Bay Princess Juliana

Wed 2/18

3:15 pm-12:18 am

1 stop11h 03m

$360

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/24

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Mon 2/2

3:15 pm-9:12 am

2 stops19h 57m

$399

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 1/15

10:07 am-2:10 pm

2 stops26h 03m

Simpson Bay Princess Juliana

Sun 1/18

3:15 pm-9:12 am

2 stops19h 57m

$421

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 3/7

5:05 am-3:40 pm

1 stop8h 35m

Simpson Bay Princess Juliana

Sat 3/14

3:40 pm-12:01 am

1 stop9h 21m

$446

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 2/10

9:23 am-8:30 am

2 stops21h 07m

Simpson Bay Princess Juliana

Tue 2/17

3:15 pm-11:27 am

1 stop22h 12m

$448

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/24

5:52 pm-2:40 pm

1 stop18h 48m

Simpson Bay Princess Juliana

Sun 2/1

5:36 pm-7:36 pm

1 stop28h 00m

$455

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 1/29

7:45 am-4:21 pm

2 stops30h 36m

Simpson Bay Princess Juliana

Mon 2/2

5:00 pm-11:06 am

2 stops20h 06m

$466

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

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 December.

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
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 49% 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

8,008 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

8,008 reviews

Delta

7.9

Good

8,008 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

United Airlines

7.4

Good

9,095 reviews

Delta

7.9

Good

8,008 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

American Airlines

7.2

Good

11,050 reviews

Delta

7.9

Good

8,008 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

JetBlue

7.2

Good

2,899 reviews

Delta

7.9

Good

8,008 reviews

Reviews

1 / 20

6.0

Good

Jim,Nov 2025

AVL - ATL

Spirit Airlines

6.3

Okay

8,179 reviews

Delta

7.9

Good

8,008 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 $231, 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?
Delta, at $292, was found to be the cheapest airline from Chicago O'Hare Intl Airport to Simpson Bay.Alternate airlines to your destination round-trip include Spirit Airlines and United Airlines. These flights start at 57% 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 $503, 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 $230 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
Delta	Cheapest$292	Average$755	FlexibilityNo cancel fee	On-timeN/A
Spirit Airlines	Cheapest$315	Average$399	FlexibilityNo cancel fee	On-time65%
United Airlines	Cheapest$410	Average$815	FlexibilityNo cancel fee	On-time69%
JetBlue	Cheapest$535	Average$711	FlexibilityNo cancel fee	On-time62%
American Airlines	Cheapest$540	Average$704	FlexibilityNo cancel fee	On-time71%

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$77+ 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 2/9. 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

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 December 12, 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 December 12, 2025.

Find 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

Cheapflights Fare Finder

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

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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?

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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 December 12, 2025.