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O'Hare Intl

$203+ Cheap flights from Simpson Bay (SXM) to O'Hare Intl (ORD)

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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — ORD
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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Cheap flight deals from Simpson Bay to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Simpson Bay (SXM) to O'Hare Intl (ORD). 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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$497
(American Airlines)

One-way from

$203
(Cheapflightsfares)

Good one-way deal

$389 or less
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago O'Hare Intl flights.
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From Simpson Bay Princess Juliana to Chicago O'Hare Intl
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One-way flight from Simpson Bay Princess Juliana to Chicago O'Hare Intl
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Price to beat on a one-way flight from Simpson Bay Princess Juliana to Chicago O'Hare Intl.
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Find flight deals from Simpson Bay to O'Hare Intl

Cheapest flights from Simpson Bay to O'Hare Intl
Explore the most affordable flight options available from Simpson Bay to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2025.

This Trip.com deal was found by Cheapflights users on 9/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/233:00 pmSXM - ORD
Nonstop6h 00mUnited Airlines
Sun 11/308:45 amORD - SXM
Nonstop5h 12mUnited Airlines
Deal found 9/29$390
This United Airlines deal was found by Cheapflights users on 9/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/261:20 pmSXM - ORD
Nonstop6h 01mUnited Airlines
Sun 11/28:45 amORD - SXM
Nonstop5h 12mUnited Airlines
Deal found 9/29$436
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Sun 11/235:24 pmSXM - ORD
2 stops23h 33mAmerican Airlines
Sun 11/305:00 amORD - SXM
1 stop7h 00mAmerican Airlines
Deal found 9/29$489
This Kissandfly.com deal was found by Cheapflights users on 9/29. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2611:30 amSXM - ORD
2 stops22h 52mMultiple Airlines
Sun 11/28:28 amORD - SXM
2 stops27h 47mMultiple Airlines
Deal found 9/29$547
This Cheapflightsfares deal was found by Cheapflights users on 9/28. 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 10/43:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Fri 10/107:43 pmORD - SXM
1 stop17h 17mSpirit Airlines
Deal found 9/28$633
This Expedia deal was found by Cheapflights users on 9/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/264:45 pmSXM - ORD
1 stop29h 07mJetBlue
Sun 11/25:45 amORD - SXM
1 stop7h 53mJetBlue
Deal found 9/29$644

Cheapflights Fare Finder

 
Customize your flight search to find flights from Simpson Bay to O'Hare Intl 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 September 29, 2025.
Use the filters below to find and compare flights from Simpson Bay to Chicago O'Hare Intl Airport that are best for you.

Fly from

Simpson Bay

Fly to

O'Hare Intl

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 11/23

3:00 pm-7:00 pm

Nonstop6h 00m

Chicago O'Hare Intl

Sun 11/30

8:45 am-3:57 pm

Nonstop5h 12m

$390

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 10/26

1:20 pm-6:21 pm

Nonstop6h 01m

Chicago O'Hare Intl

Sun 11/2

8:45 am-3:57 pm

Nonstop5h 12m

$436

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 11/23

5:24 pm-2:57 pm

2 stops23h 33m

Chicago O'Hare Intl

Sun 11/30

5:00 am-2:00 pm

1 stop7h 00m

$489

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 2/14

2:40 pm-6:40 pm

Nonstop6h 00m

Chicago O'Hare Intl

Sat 2/21

1:00 pm-1:50 pm

1 stop22h 50m

$537

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 10/26

11:30 am-9:22 am

2 stops22h 52m

Chicago O'Hare Intl

Sun 11/2

8:28 am-2:15 pm

2 stops27h 47m

$547

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 3/6

4:55 pm-11:12 pm

1 stop8h 17m

Chicago O'Hare Intl

Tue 3/10

9:13 pm-12:51 pm

1 stop14h 38m

$587

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/6

4:28 pm-11:42 pm

1 stop9h 14m

$203

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 10/24

3:05 pm-6:38 pm

1 stop28h 33m

$230

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 12/24

5:00 pm-3:10 pm

1 stop24h 10m

$262

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 10/27

3:05 pm-6:38 pm

1 stop28h 33m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

Showing 1-10 of 14 results
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Compare providers for flights from Simpson Bay to O'Hare Intl

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 Simpson Bay to O'Hare Intl in September.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice 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 Simpson Bay-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Simpson Bay-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Simpson Bay-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Simpson Bay-Chicago O'Hare Intl Airport 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 Simpson Bay-Chicago O'Hare Intl Airport 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 Simpson Bay to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Simpson Bay 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.

Related info for your journey

Find useful and relevant information for your journey from Simpson Bay to O'Hare Intl. 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 from for flights from Simpson Bay to Chicago O'Hare Intl?

    Most people fly from Simpson Bay Princess Juliana (SXM) if they book a flight from Simpson Bay to Chicago O'Hare Intl. On average, Princess Juliana has 0 outbound flights to Chicago O'Hare Intl per day from 0 airlines. Simpson Bay Princess Juliana is conveniently located just 0.5 mi from Simpson Bay’s city center.

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

    For as low as $390, United Airlines can have you in Chicago O'Hare Intl Airport from Simpson Bay in 6h. The distance from Simpson Bay to Chicago O'Hare Intl Airport is about 2204 mi. This flight may include one or multiple stops.

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

    On average you can expect to pay $479 for a flight from Simpson Bay to Chicago O'Hare Intl Airport. The cheapest flight overall is $226 while the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl) is currently priced at $537.

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

    Yes. In addition to deals on Simpson Bay to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Simpson Bay to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Simpson Bay to O'Hare Intl.

  • Can I find deals for business class flights from Simpson Bay to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Simpson Bay to O'Hare Intl 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 Simpson Bay to Chicago O'Hare Intl Airport?

    Currently, August is the cheapest month in which you can book a flight from Simpson Bay to Chicago O'Hare Intl Airport (average of $245). Flying from Simpson Bay to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Skokie
Gurnee
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Elgin
Arlington Heights
Orland Park
Beloit
Racine
Rockford
Oak Brook
Elk Grove Village
Downers Grove
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Bridgeview
Warrenville
Joliet

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