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Simpson Bay

$139+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
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 August or September, 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 August 20, 2025.

Round-trip from

$296
(Cheapflightsfares)

One-way from

$139
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$585

Good round-trip deal

$797 or less

Good one-way deal

$353 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. 9% potential increase in price ($73 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 August 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 August 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 9/65:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 9/133:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/17$296
This Cheapflightsfares deal was found by Cheapflights users on 8/19. 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 9/275:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 10/43:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/19$337
This Cheapflightsfares deal was found by Cheapflights users on 8/19. 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.
Fri 9/195:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Mon 9/293:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/19$350
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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.
Fri 10/245:05 amORD - SXM
1 stop7h 54mSpirit Airlines
Fri 10/313:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Deal found 8/17$362
This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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.
Tue 11/115:59 pmORD - SXM
1 stop19h 11mSpirit Airlines
Sat 11/154:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 8/20$369
This FlightHub deal was found by Cheapflights users on 8/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:29 pmORD - SXM
1 stop17h 30mSpirit Airlines
Mon 10/203:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 8/20$371
This FlightHub deal was found by Cheapflights users on 8/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/185:05 amORD - SXM
1 stop7h 54mSpirit Airlines
Sat 10/253:05 pmSXM - ORD
1 stop20h 42mSpirit Airlines
Deal found 8/19$390
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 12/65:05 amORD - SXM
1 stop8h 05mSpirit Airlines
Sat 12/134:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 8/17$394
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Sat 10/115:05 amORD - SXM
1 stop7h 54mSpirit Airlines
Sat 10/183:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 8/18$400
This Priceline deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 10/113:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 8/20$402

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 August 20, 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

Sat 9/6

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 9/13

3:05 pm-10:48 pm

1 stop8h 43m

$296

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/11

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Sat 10/18

3:05 pm-11:45 pm

1 stop9h 40m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/20

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 9/27

3:05 pm-10:48 pm

1 stop8h 43m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/27

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 10/4

3:05 pm-10:48 pm

1 stop8h 43m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/18

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Sat 10/25

3:05 pm-11:45 pm

1 stop9h 40m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 9/19

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Mon 9/29

3:05 pm-10:48 pm

1 stop8h 43m

$350

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 10/24

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Fri 10/31

3:05 pm-1:03 am

1 stop10h 58m

$362

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 11/11

5:59 pm-3:10 pm

1 stop19h 11m

Simpson Bay Princess Juliana

Sat 11/15

4:28 pm-11:42 pm

1 stop9h 14m

$369

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 10/16

7:29 pm-1:59 pm

1 stop17h 30m

Simpson Bay Princess Juliana

Mon 10/20

3:05 pm-11:45 pm

1 stop9h 40m

$371

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/31

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sat 2/7

4:28 pm-11:42 pm

1 stop9h 14m

$379

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 21 results
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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 August 8, 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 $459). Flying from Chicago O'Hare Intl Airport to Simpson Bay in March is currently the most expensive (average of $654). 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 August 20, 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 53% on the cost of your flight, compared to a flight in the morning.

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 August 20, 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
7,982 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

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
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

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!
United Airlines
7.4
Good
8,928 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

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
7,982 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

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
8,039 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Boarding

8.2

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

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 $296, Spirit Airlines can have you in Simpson Bay from Chicago O'Hare Intl Airport in 7h 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 $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 American Airlines. These flights start at 56% 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 $625, our data shows the cheapest flight currently is $313. When looking at the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana), you can expect to pay $337 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 $654). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Simpson Bay?

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

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Alternative routes for O'Hare Intl to Simpson Bay

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

Top 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$564Average$806FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$616Average$711FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$654Average$894FlexibilityNo cancel feeOn-time69%

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