HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$119+ 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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Feb 9 — Feb 161
Sun 2/9
Sun 2/16
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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 21 days in advance, depart on a Monday or Tuesday 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 February 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$405
(Cheapflightsfares)

One-way from

$119
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$702

Good round-trip deal

$945 or less

Good one-way deal

$378 or less
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
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
Highest demand for flights based on searches. 9% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Simpson Bay Princess Juliana.
Search Deals
Price to beat on a 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 February 4, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 4/195:10 amORD - SXM
1 stop7h 17mSpirit Airlines
Fri 4/252:33 pmSXM - ORD
1 stop11h 08mSpirit Airlines
Deal found 2/4$405
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Tue 3/117:42 pmORD - SXM
1 stop16h 46mMultiple Airlines
Mon 3/246:35 pmSXM - ORD
1 stop15h 31mMultiple Airlines
Deal found 2/3$408
This Travelocity deal was found by Cheapflights users on 2/3. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/238:30 pmORD - SXM
1 stop17h 45mAir Canada
Sun 3/303:55 pmSXM - ORD
2 stops27h 35mAir Canada
Deal found 2/3$570
This Frontier deal was found by Cheapflights users on 2/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/306:01 pmORD - SXM
2 stops15h 57mFrontier
Sat 6/1412:18 pmSXM - ORD
1 stop12h 20mFrontier
Deal found 2/4$602
This American Airlines deal was found by Cheapflights users on 2/4. 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.
Wed 3/55:10 amORD - SXM
2 stops9h 10mAmerican Airlines
Wed 3/122:10 pmSXM - ORD
2 stops11h 02mAmerican Airlines
Deal found 2/4$627
This Delta deal was found by Cheapflights users on 2/3. 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.
Sun 9/146:00 amORD - SXM
1 stop6h 50mDelta
Wed 9/243:15 pmSXM - ORD
1 stop9h 40mDelta
Deal found 2/3$632

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 2,558,603 searches. Data last updated February 4, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/19

5:10 am-1:27 pm

1 stop7h 17m

Simpson Bay Princess Juliana

Fri 4/25

2:33 pm-12:41 am

1 stop11h 08m

$405

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 3/11

7:42 pm-1:28 pm

1 stop16h 46m

Simpson Bay Princess Juliana

Mon 3/24

6:35 pm-9:06 am

1 stop15h 31m

$408

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/23

8:30 pm-3:15 pm

1 stop17h 45m

Simpson Bay Princess Juliana

Sun 3/30

3:55 pm-6:30 pm

2 stops27h 35m

$570

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 5/30

6:01 pm-10:58 am

2 stops15h 57m

Simpson Bay Princess Juliana

Sat 6/14

12:18 pm-11:38 pm

1 stop12h 20m

$602

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 3/6

9:25 am-5:15 pm

2 stops29h 50m

$119

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/12

5:10 am-1:28 pm

1 stop7h 18m

$124

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 3/24

8:33 pm-11:20 am

2 stops37h 47m

$168

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 3/15

6:58 pm-2:20 pm

1 stop18h 22m

$308

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 3/15

8:45 am-2:52 pm

Nonstop5h 07m

$513

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust 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 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 January 31, 2025.

The best time to book flights from Chicago O'Hare Intl Airport to Simpson Bay is 21 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.

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 $459). 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 February 4, 2025.

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 54% 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 February 4, 2025.
See what other customers who have flown with United Airlines, American Airlines and Air Canada 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.
United Airlines
7.4
Good
8,887 reviews

Comfort

7.3

Food

6.7

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

United Airlines
7.4
Good
8,887 reviews
United Airlines
7.4
Good
8,887 reviews

Comfort

7.3

Food

6.7

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,887 reviews

Comfort

7.3

Food

6.7

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Air Canada
7.0
Good
8,667 reviews
United Airlines
7.4
Good
8,887 reviews

Comfort

7.3

Food

6.7

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Spirit Airlines
6.3
Okay
8,076 reviews
United Airlines
7.4
Good
8,887 reviews

Comfort

7.3

Food

6.7

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Frontier
6.0
Okay
3,416 reviews
United Airlines
7.4
Good
8,887 reviews

Comfort

7.3

Food

6.7

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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.

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

    Spirit Airlines, at $405, was found to be the cheapest airline from Chicago O'Hare Intl Airport to Simpson Bay.Alternate airlines to your destination round-trip include Air Canada and American Airlines. These flights start at 46% 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 Frontier ($119), Spirit Airlines ($124), and American Airlines ($308).

  • 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 $925, our data shows the cheapest flight currently is $308. When looking at the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana), you can expect to pay $309 for that flight.

  • 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.

  • 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 $459). 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 2,558,603 searches. Data last updated February 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$298Average$445FlexibilityNo cancel feeOn-time65%
DeltaCheapest$554Average$774FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$581Average$732FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$645Average$879FlexibilityNo 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.