HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$128+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Nov 4 — Nov 111
1 adult
Mon 11/4
Mon 11/11
We work with more than 300 partners to bring you better travel deals

...and more

Find cheap flights from O'Hare Intl to Simpson Bay with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Chicago O'Hare Intl to Simpson Bay Princess Juliana are usually found in September or May, booked 64 days in advance, depart on a Monday or Wednesday 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 October 30, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

September

Round-trip from

$361
(Kiwi.com)

One-way from

$128
(Cheapflightsfares)
Provider with most accurate pricing for Chicago O'Hare Intl-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Simpson Bay Princess Juliana flights.
Search Deals
High demand for flights, 20% potential price rise
Search Deals
Best time to find cheap flights, 19% potential price drop
Search Deals
From Chicago O'Hare Intl to Simpson Bay Princess Juliana
Search Deals
One-way flight from Chicago O'Hare Intl to Simpson Bay Princess Juliana
Search Deals

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 October 30, 2024.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/156:35 amORD - SXM
2 stops32h 04mMultiple Airlines
Mon 11/183:25 pmSXM - ORD
1 stop29h 16mMultiple Airlines
Deal found 10/28$361
This CheapOair deal was found by Cheapflights users on 10/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/127:46 pmORD - SXM
1 stop16h 44mSpirit Airlines
Fri 11/153:25 pmSXM - ORD
1 stop20h 10mSpirit Airlines
Deal found 10/29$426
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/79:50 amORD - SXM
2 stops28h 05mAir Canada
Sat 12/145:45 pmSXM - ORD
1 stop17h 12mAir Canada
Deal found 10/29$539
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:40 amORD - SXM
1 stop7h 31mDelta
Tue 1/214:40 pmSXM - ORD
1 stop9h 17mDelta
Deal found 10/29$620
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Sat 12/76:45 pmORD - SXM
1 stop17h 45mAmerican Airlines
Tue 12/173:30 pmSXM - ORD
1 stop10h 28mAmerican Airlines
Deal found 10/30$630
This United deal was found by Cheapflights users on 10/30. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/78:45 amORD - SXM
Nonstop5h 07mUnited Airlines
Tue 12/172:53 pmSXM - ORD
1 stop10h 07mUnited Airlines
Deal found 10/30$740
This CheapOair deal was found by Cheapflights users on 10/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/318:29 pmORD - SXM
2 stops43h 05mFrontier
Sat 11/95:49 pmSXM - ORD
2 stops24h 07mFrontier
Deal found 10/29$973

Find flights from O'Hare Intl to Simpson Bay within your budget

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 2,570,725 searches. Data last updated October 30, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$361 - $715

Route

Depart

Return

Price

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 11/15

2 stops32h 04m

Simpson Bay Princess Juliana

Mon 11/18

1 stop29h 16m

$361

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 1/22

1 stop7h 16m

Simpson Bay Princess Juliana

Wed 1/29

1 stop9h 26m

$394

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/24

2 stops19h 07m

Simpson Bay Princess Juliana

Sat 2/1

2 stops17h 23m

$427

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 12/7

2 stops28h 05m

Simpson Bay Princess Juliana

Sat 12/14

1 stop17h 12m

$539

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 12/31

1 stop7h 31m

Simpson Bay Princess Juliana

Tue 1/21

1 stop9h 17m

$620

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 12/7

1 stop17h 45m

Simpson Bay Princess Juliana

Tue 12/17

1 stop10h 28m

$630

Chicago O'Hare IntlSimpson Bay Princess Juliana

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/5

Nonstop5h 07m

Simpson Bay Princess Juliana

Mon 1/13

1 stop10h 04m

$715

Flights are sorted by cheapest first

Deals found on 10/28

Compare providers for flights from O'Hare Intl to Simpson Bay

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 O'Hare Intl to Simpson Bay in October.
ProviderPrice AccuracyTrust Score*Cancellation Policy
ExpediaPrice Accuracy1 starTrust Score*3 starsCancellation PolicyAirline Policy
FlightHubPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
eDreamsPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
MytripPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy

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

Travel insights for flights from O'Hare Intl to Simpson Bay

Get recent, data-driven insights about flights from O'Hare Intl to Simpson Bay including ideal travel times, pricing trends, and more.

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 October 25, 2024.

The best time to book flights from Chicago O'Hare Intl Airport to Simpson Bay is 64 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.

Find deals

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 $462). Flying from Chicago O'Hare Intl Airport to Simpson Bay in July is currently the most expensive (average of $684). 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 October 30, 2024.

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 40% 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 October 30, 2024.
See what other customers who have flown with American Airlines, Air Canada and Spirit Airlines from Chicago to Simpson Bay have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,836 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Delta
8.0
Very good
8,836 reviews
Delta
8.0
Very good
8,836 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

JetBlue
7.5
Good
3,520 reviews
Delta
8.0
Very good
8,836 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

United Airlines
7.4
Good
9,240 reviews
Delta
8.0
Very good
8,836 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

WestJet
7.3
Good
2,804 reviews
Delta
8.0
Very good
8,836 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

American Airlines
7.3
Good
10,000 reviews
Delta
8.0
Very good
8,836 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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.

  • Can I find flights from Chicago O'Hare Intl Airport to Simpson Bay for under $400 on Cheapflights?

    Yes, there are multiple flights from Chicago O'Hare Intl Airport to Simpson Bay for under $400. The cheapest flight booked recently is on Multiple Airlines for just $361, but on average you can expect to pay $526.

  • Are there nonstop flights from Chicago O'Hare Intl Airport to Simpson Bay for under $700 on Cheapflights?

    Cheapflights has at least 1 direct flight from Chicago O'Hare Intl Airport to Simpson Bay under $700. A good price for a nonstop flight from Chicago O'Hare Intl Airport to Simpson Bay is less than $665.

  • Are there last-minute flights available from Chicago O'Hare Intl Airport to Simpson Bay for under $500?

    There are currently 5+ open flights from Chicago O'Hare Intl Airport to Simpson Bay within the next 7 days for less than $500.

  • What days are nonstop flights available from Chicago O'Hare Intl Airport to Simpson Bay?

    Days when nonstop flights are available for this flight are: Friday.

  • How many flights depart from Chicago O'Hare Intl Airport to Simpson Bay on average per day?

    Travelers can expect 1 flight from Chicago O'Hare Intl Airport to Simpson Bay on average per day.
    Morning (6am - Noon) - 100% of flight departures

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

    For as low as $394, Spirit Airlines can have you in Simpson Bay from Chicago O'Hare Intl Airport in 7h 16m. There are 2217 mi between Chicago O'Hare Intl Airport and Simpson Bay. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Simpson Bay round-trip?

    Spirit Airlines, at $394, was found to be the cheapest airline from Chicago O'Hare Intl Airport to Simpson Bay.Alternate airlines to your destination round-trip include Frontier and Air Canada. These flights start at 45% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Simpson Bay one-way?

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Simpson Bay are Spirit Airlines ($128), JetBlue ($197), and Air Canada ($248).

  • 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 $852, our data shows the cheapest flight currently is $327. When looking at the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana), you can expect to pay $361 for that flight.

  • What does ORD to SXM mean?

    Chicago O'Hare Intl Airport is ORD and Simpson Bay Princess Juliana Airport is SXM. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service.

  • Can I find deals for flights from O'Hare Intl to Simpson Bay that include extra baggage allowance?

    The amount of baggage you can bring on your O'Hare Intl to Simpson Bay flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from O'Hare Intl to Simpson Bay with specific airlines?

    Yes, Cheapflights allows you to browse and filter O'Hare Intl to Simpson Bay flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from O'Hare Intl to Simpson Bay that allow pets onboard?

    Many airlines flying from O'Hare Intl to Simpson Bay offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from O'Hare Intl to Simpson Bay?

    Yes, you can often find last-minute deals on O'Hare Intl to Simpson Bay flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago O'Hare Intl Airport to Simpson Bay flight deals updated?

    The Chicago O'Hare Intl Airport to Simpson Bay flight deals you see on this page were last updated on 10/30.

  • 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 $462). Flying from Chicago O'Hare Intl Airport to Simpson Bay in July is currently the most expensive (average of $684). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 2,570,725 searches. Data last updated October 30, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$270Average$481FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$551Average$716FlexibilityNo cancel feeOn-time71%
DeltaCheapest$554Average$709FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$613Average$855FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines