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O'Hare Intl

$148+ 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
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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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 November 13, 2025.

This Mytrip deal was found by Cheapflights users on 11/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/213:20 pmSXM - ORD
2 stops23h 36mSpirit Airlines
Fri 11/285:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Deal found 11/11$418
This Priceline deal was found by Cheapflights users on 11/11. 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.
Fri 11/215:00 pmSXM - ORD
1 stop24h 10mMultiple Airlines
Fri 11/285:00 amORD - SXM
1 stop7h 15mMultiple Airlines
Deal found 11/11$421
This Gotogate deal was found by Cheapflights users on 11/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/283:40 pmSXM - ORD
2 stops29h 48mAir Canada
Sun 1/48:15 pmORD - SXM
2 stops40h 25mAir Canada
Deal found 11/11$513
This Mytrip deal was found by Cheapflights users on 11/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2811:30 amSXM - ORD
3 stops25h 44mMultiple Airlines
Sun 1/412:09 pmORD - SXM
3 stops24h 06mMultiple Airlines
Deal found 11/11$604
This Kissandfly.com deal was found by Cheapflights users on 11/11. 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 12/282:20 pmSXM - ORD
Nonstop6h 01mLufthansa
Sun 1/48:45 amORD - SXM
Nonstop5h 12mLufthansa
Deal found 11/11$623
This Vliegwinkel deal was found by Cheapflights users on 11/11. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/153:20 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Sat 11/225:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Deal found 11/11$729

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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$377
(United Airlines)

One-way from

$148
(Super.com)

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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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 November 13, 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

Fri 3/6

4:55 pm-11:43 pm

1 stop8h 48m

Chicago O'Hare Intl

Tue 3/10

6:05 am-2:51 pm

1 stop7h 46m

$377

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 2/14

3:00 pm-6:54 pm

Nonstop5h 54m

Chicago O'Hare Intl

Sat 2/21

6:48 pm-2:19 pm

1 stop17h 31m

$397

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 3/6

5:33 pm-11:00 am

2 stops19h 27m

Chicago O'Hare Intl

Tue 3/10

7:00 pm-3:10 pm

2 stops19h 10m

$437

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 12/28

3:40 pm-7:28 pm

2 stops29h 48m

Chicago O'Hare Intl

Sun 1/4

8:15 pm-2:40 pm

2 stops40h 25m

$513

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/13

3:20 pm-12:09 am

1 stop10h 49m

$187

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 2/9

3:09 pm-8:54 pm

1 stop31h 45m

$191

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 1/7

3:20 pm-7:24 pm

1 stop30h 04m

$198

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 1/9

3:09 pm-11:35 am

2 stops22h 26m

$206

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 12/12

3:20 pm-12:09 am

1 stop10h 49m

$213

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 12/12

3:20 pm-11:54 am

2 stops22h 34m

$214

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 12 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 November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 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 November 13, 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 $397, United Airlines can have you in Chicago O'Hare Intl Airport from Simpson Bay in 5h 54m. 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 $515 for a flight from Simpson Bay to Chicago O'Hare Intl Airport. The cheapest flight overall is $381 while the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl) is currently priced at $377.

  • 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
Skokie
Des Plaines
Gurnee
Hoffman Estates
Beloit
Delavan
Elgin
Oak Brook
Elk Grove Village
Downers Grove
Rockford
Naperville
Orland Park
Bridgeview
Warrenville
Waukegan
Aurora
Racine

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