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O'Hare Intl

$163+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — ORD
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap 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 December 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
Wed 12/313:20 pmSXM - ORD
2 stops25h 01mMultiple Airlines
Sun 1/44:44 pmORD - SXM
1 stop19h 31mMultiple Airlines
Deal found 12/26$464
This Expedia deal was found by Cheapflights users on 12/26. 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.
Wed 12/315:00 pmSXM - ORD
2 stops51h 53mAir Canada
Sun 1/46:00 pmORD - SXM
2 stops42h 40mAir Canada
Deal found 12/26$519
This United Airlines deal was found by Cheapflights users on 12/26. 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.
Wed 12/314:55 pmSXM - ORD
1 stop8h 49mUnited Airlines
Sun 1/48:45 amORD - SXM
Nonstop5h 12mUnited Airlines
Deal found 12/26$715
This Delta deal was found by Cheapflights users on 12/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/275:22 pmSXM - ORD
1 stop8h 40mDelta
Sat 1/35:30 amORD - SXM
1 stop8h 27mDelta
Deal found 12/27$805
This United Airlines deal was found by Cheapflights users on 12/27. 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.
Sat 12/272:52 pmSXM - ORD
1 stop10h 43mUnited Airlines
Sat 1/38:45 amORD - SXM
Nonstop5h 12mUnited Airlines
Deal found 12/27$861
This Air Canada deal was found by Cheapflights users on 12/27. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/275:00 pmSXM - ORD
1 stop22h 01mAir Canada
Sat 1/38:40 pmORD - SXM
2 stops16h 00mAir Canada
Deal found 12/27$986

Find 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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$265
(Cheapflightsfares)

One-way from

$163
(Super.com)
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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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 December 28, 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

Sat 1/17

3:15 pm-11:46 pm

1 stop10h 31m

Chicago O'Hare Intl

Sat 1/24

5:32 pm-2:10 pm

1 stop18h 38m

$304

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 2/9

3:20 pm-11:47 pm

1 stop10h 27m

Chicago O'Hare Intl

Mon 2/16

5:15 am-2:15 pm

1 stop7h 00m

$305

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 2/9

3:20 pm-11:22 am

1 stop22h 02m

Chicago O'Hare Intl

Mon 2/16

9:41 pm-2:15 pm

2 stops14h 34m

$344

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/17

3:43 pm-7:36 pm

1 stop29h 53m

Chicago O'Hare Intl

Sat 1/24

9:40 am-4:21 pm

1 stop28h 41m

$351

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/17

5:00 pm-11:06 am

2 stops20h 06m

Chicago O'Hare Intl

Sat 1/24

10:35 am-2:40 pm

1 stop26h 05m

$405

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 2/28

3:20 pm-10:39 pm

1 stop9h 19m

$168

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/24

3:10 pm-10:44 pm

1 stop9h 34m

$168

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 2/27

3:20 pm-7:50 pm

1 stop30h 30m

$176

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 1/22

3:15 pm-10:36 pm

1 stop9h 21m

$176

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 2/26

3:20 pm-11:05 pm

1 stop9h 45m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 15 results
1
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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 December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Simpson Bay-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

Cheapflights Insights

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

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

Find hourly flight availability from Simpson Bay to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 28, 2025.

When flying from Simpson Bay to Chicago O'Hare Intl Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 $304, Spirit Airlines can have you in Chicago O'Hare Intl Airport from Simpson Bay in 10h 31m. The distance from Simpson Bay to Chicago O'Hare Intl Airport is about 2204 mi.

  • 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.

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
Gurnee
Elgin
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Lake Geneva
Bridgeview
Kenosha
Warrenville
Waukegan
Aurora
Evanston

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