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O'Hare Intl

$200+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — ORD
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$373
(Mytrip)

One-way from

$200
(Cheapflightsfares)

Good one-way deal

$399 or less
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 August 14, 2025.

This Mytrip deal was found by Cheapflights users on 8/12. 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.
Sat 9/203:05 pmSXM - ORD
2 stops20h 37mSpirit Airlines
Sat 9/275:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Deal found 8/12$373
This Mytrip deal was found by Cheapflights users on 8/14. 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.
Sat 9/133:05 pmSXM - ORD
2 stops20h 37mSpirit Airlines
Sat 9/205:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Deal found 8/14$378
This Mytrip deal was found by Cheapflights users on 8/13. 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.
Sat 9/63:05 pmSXM - ORD
2 stops20h 37mSpirit Airlines
Sat 9/135:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Deal found 8/13$389
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/223:05 pmSXM - ORD
1 stop20h 47mSpirit Airlines
Mon 9/295:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Deal found 8/11$398
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/83:05 pmSXM - ORD
1 stop20h 47mSpirit Airlines
Sun 9/1411:57 amORD - SXM
1 stop25h 03mSpirit Airlines
Deal found 8/11$425

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 August 14, 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 9/20

3:05 pm-10:42 am

2 stops20h 37m

Chicago O'Hare Intl

Sat 9/27

5:05 am-2:00 pm

1 stop7h 55m

$373

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/13

3:05 pm-10:42 am

2 stops20h 37m

Chicago O'Hare Intl

Sat 9/20

5:05 am-2:00 pm

1 stop7h 55m

$378

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-10:42 am

2 stops20h 37m

Chicago O'Hare Intl

Sat 9/13

5:05 am-2:00 pm

1 stop7h 55m

$389

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 9/22

3:05 pm-10:52 am

1 stop20h 47m

Chicago O'Hare Intl

Mon 9/29

5:05 am-2:00 pm

1 stop7h 55m

$398

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 9/8

3:05 pm-10:52 am

1 stop20h 47m

Chicago O'Hare Intl

Sun 9/14

11:57 am-2:00 pm

1 stop25h 03m

$425

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 10/11

3:05 pm-11:45 pm

1 stop9h 40m

$200

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 11/12

4:28 pm-11:42 pm

1 stop9h 14m

$200

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/13

3:05 pm-10:48 pm

1 stop8h 43m

$215

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/13

3:05 pm-7:44 pm

2 stops29h 39m

$219

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 9/15

3:05 pm-10:48 pm

1 stop8h 43m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 12 results
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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.

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

    On average you can expect to pay $399 for a flight from Simpson Bay to Chicago O'Hare Intl Airport. The cheapest flight overall is $389 while the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl) is currently priced at $425.

  • 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
Beloit
Hoffman Estates
Skokie
Des Plaines
Elgin
Gurnee
Arlington Heights
Racine
Rockford
Great Lakes
Orland Park
Merrillville
Naperville
Waukegan
Elk Grove Village
Downers Grove
Tinley Park
Evanston

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