What is the cheapest airline to fly from Chicago O'Hare Intl Airport to Simpson Bay round-trip?

Spirit Airlines, at $357, was found to be the cheapest airline from Chicago O'Hare Intl Airport to Simpson Bay.. This flight start at 51% lower than the current average price 3 months from now.

What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Simpson Bay one-way?

The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Simpson Bay are Spirit Airlines ($156), Delta ($293), and American Airlines ($294).

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Simpson Bay?

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Simpson Bay flight should consider departing on Tuesday mornings when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 $752, our data shows the cheapest flight currently is $607. When looking at the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana), you can expect to pay $357 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, Delta or Spirit Airlines.

What is the cheapest day to fly round-trip from Chicago O'Hare Intl Airport to Simpson Bay?

Travelers have found that booking a Monday departure is the best way to save up to 29% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

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

September can be a great time to fly to Simpson Bay from Chicago O'Hare Intl Airport with a flight ticket averaging about $719. Cheapflights users have found deals in the month of September for as cheap as $237. The most expensive prices can be found in the month of March.

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.

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.

$156+ Flights from Chicago O'Hare Intl Airport to Simpson Bay

Q: How far in advance should I book a flight from Chicago O'Hare Intl Airport to Simpson Bay?

To save on the cost of your flight from Chicago O'Hare Intl Airport to Simpson Bay, book at least 26 days before your planned departure. Booking around this time can save you about 74% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $389 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $1,114.

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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”

2. Select your favorite providers

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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Simpson Bay Princess Juliana are usually found in May or July, booked 17 days in advance, depart on a Monday or Tuesday and return on a Monday

Cheap flight deals from O'Hare Intl to Simpson Bay

Round-trip from	$357 (Cheapflightsfares)
One-way from	$156 (Booking.com)
Popular in	December
Cheapest in	May
Average price	$672
Good round-trip deal	$707 or less

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. 7% potential increase in price ($63 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 July 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 July 3, 2025.

Wed 8/135:05 amORD - SXM

1 stop7h 55mSpirit Airlines

Wed 8/203:05 pmSXM - ORD

1 stop9h 54mSpirit Airlines

Deal found 7/2

$357

Fri 7/114:26 pmORD - SXM

1 stop18h 02mMultiple Airlines

Wed 7/233:05 pmSXM - ORD

1 stop9h 08mMultiple Airlines

Deal found 7/2

$370

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 July 3, 2025.

Wed 8/135:05 amORD - SXM

1 stop7h 55mSpirit Airlines

Wed 8/203:05 pmSXM - ORD

1 stop9h 54mSpirit Airlines

Deal found 7/1

$357

Fri 7/114:26 pmORD - SXM

1 stop18h 02mMultiple Airlines

Wed 7/233:05 pmSXM - ORD

1 stop9h 08mMultiple Airlines

Deal found 7/2

$370

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 July 3, 2025 and is based on user searches.

Tue 7/81:07 amORD - SXM

1 stop9h 17mCopa Airlines

Sun 7/1312:23 pmSXM - ORD

1 stop12h 57mCopa Airlines

Deal found 7/2

$1,132

Fri 7/114:26 pmORD - SXM

1 stop18h 02mMultiple Airlines

Wed 7/233:05 pmSXM - ORD

1 stop9h 08mMultiple Airlines

Deal found 7/2

$370

Fri 7/114:36 pmORD - SXM

2 stops20h 24mSpirit Airlines

Wed 7/233:05 pmSXM - ORD

2 stops25h 26mSpirit Airlines

Deal found 7/2

$553

Wed 8/135:05 amORD - SXM

1 stop7h 55mSpirit Airlines

Wed 8/203:05 pmSXM - ORD

1 stop9h 54mSpirit Airlines

Deal found 7/1

$357

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 July 3, 2025.

Sat 8/25:05 amORD - SXM

1 stop7h 55mSpirit Airlines

Deal found 7/2

$156

Sat 8/26:02 pmORD - SXM

3 stops24h 28mMultiple Airlines

Deal found 7/2

$258

Wed 9/105:45 amORD - SXM

1 stop7h 00mDelta

Deal found 7/2

$293

Sat 8/1610:10 pmORD - SXM

2 stops15h 59mAmerican Airlines

Deal found 7/2

$294

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

Wed 8/13

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Wed 8/20

3:05 pm-11:59 pm

1 stop9h 54m

$357

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 7/19

5:01 am-5:21 pm

2 stops11h 20m

Simpson Bay Princess Juliana

Sat 8/2

3:05 pm-11:53 pm

1 stop9h 48m

$378

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 8/2

5:05 am-2:00 pm

1 stop7h 55m

$156

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 8/2

6:02 pm-7:30 pm

3 stops24h 28m

$258

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 9/10

5:45 am-1:45 pm

1 stop7h 00m

$293

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 8/16

10:10 pm-3:09 pm

2 stops15h 59m

$294

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 12/28

8:45 am-3:52 pm

Nonstop5h 07m

$608

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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?

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 $459). Flying from Chicago O'Hare Intl Airport to Simpson Bay in March is currently the most expensive (average of $656). 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 54% 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

Peruse reviews from past customers who have flown with Delta, American Airlines, and Spirit 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

7,970 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Delta

8.0

Very good

7,970 reviews

Delta

8.0

Very good

7,970 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,970 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Spirit Airlines

6.3

Okay

8,094 reviews

Delta

8.0

Very good

7,970 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 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.
What is the cheapest airline to fly from Chicago O'Hare Intl Airport to Simpson Bay round-trip?
Spirit Airlines, at $357, was found to be the cheapest airline from Chicago O'Hare Intl Airport to Simpson Bay.. This flight start at 51% lower than the current average price 3 months from now.
What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Simpson Bay one-way?
The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Simpson Bay are Spirit Airlines ($156), Delta ($293), and American Airlines ($294).
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 $752, our data shows the cheapest flight currently is $607. When looking at the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana), you can expect to pay $357 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 $459). Flying from Chicago O'Hare Intl Airport to Simpson Bay in March is currently the most expensive (average of $656). 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 4 airlines flying from O'Hare Intl to Simpson Bay

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$330	Average$400	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$564	Average$807	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$614	Average$708	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$654	Average$895	FlexibilityNo cancel fee	On-time69%

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$156+ 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 8/2. 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 May or July, booked 17 days in advance, depart on a Monday or Tuesday and return on a Monday

Cheap flight deals from O'Hare Intl to Simpson Bay

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip 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 July 3, 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 July 3, 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.

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?

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 June 27, 2025.

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?

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 July 3, 2025.

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

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?

What is the cheapest airline to fly from Chicago O'Hare Intl Airport to Simpson Bay round-trip?

What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Simpson Bay one-way?

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?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for O'Hare Intl to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 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 July 3, 2025.