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Simpson Bay

$138+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Jan 9 — Jan 161
Thu 1/9
Thu 1/16
1 adult, Economy
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The best prices from Chicago O'Hare Intl to Simpson Bay Princess Juliana are usually found in September or May, booked 7 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 January 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$334
(Kiwi.com)

One-way from

$138
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$727
Provider with most accurate pricing for Chicago O'Hare Intl-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Simpson Bay Princess Juliana flights.
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From Chicago O'Hare Intl to Simpson Bay Princess Juliana
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One-way flight from Chicago O'Hare Intl to Simpson Bay Princess Juliana
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High demand for flights, 10% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in January 2025
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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 January 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/710:02 pmORD - SXM
2 stops17h 17mMultiple Airlines
Fri 2/146:31 pmSXM - ORD
1 stop31h 24mMultiple Airlines
Deal found 1/4$329
This Booking.com deal was found by Cheapflights users on 1/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1311:55 amORD - SXM
2 stops28h 20mFrontier
Mon 3/176:35 pmSXM - ORD
2 stops39h 30mFrontier
Deal found 1/4$384
This Cheapflightsfares deal was found by Cheapflights users on 1/4. 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 2/85:11 amORD - SXM
1 stop7h 19mSpirit Airlines
Sat 2/153:25 pmSXM - ORD
1 stop8h 38mSpirit Airlines
Deal found 1/4$386
This JetBlue deal was found by Cheapflights users on 1/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/77:25 pmORD - SXM
1 stop14h 42mJetBlue
Sat 6/143:40 pmSXM - ORD
1 stop8h 59mJetBlue
Deal found 1/4$535
This Air Canada deal was found by Cheapflights users on 1/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/258:30 pmORD - SXM
1 stop17h 45mAir Canada
Sun 3/303:55 pmSXM - ORD
1 stop23h 55mAir Canada
Deal found 1/3$598

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 January 4, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 2/7

10:02 pm-5:19 pm

2 stops17h 17m

Simpson Bay Princess Juliana

Fri 2/14

6:31 pm-11:55 pm

1 stop31h 24m

$329

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 3/13

11:55 am-5:15 pm

2 stops28h 20m

Simpson Bay Princess Juliana

Mon 3/17

6:35 pm-9:05 am

2 stops39h 30m

$384

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/8

5:11 am-2:30 pm

1 stop7h 19m

Simpson Bay Princess Juliana

Sat 2/15

3:25 pm-10:03 pm

1 stop8h 38m

$386

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 3/25

8:30 pm-3:15 pm

1 stop17h 45m

Simpson Bay Princess Juliana

Sun 3/30

3:55 pm-2:50 pm

1 stop23h 55m

$598

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/1

5:11 am-2:30 pm

1 stop7h 19m

$154

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/8

12:25 pm-11:20 am

2 stops20h 55m

$196

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 1/9

8:30 pm-4:15 pm

1 stop17h 45m

$340

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/9

8:45 am-3:52 pm

Nonstop5h 07m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/3

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice 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 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 3, 2025.

The best time to book flights from Chicago O'Hare Intl Airport to Simpson Bay is 7 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 March 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 January 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 48% on the cost of your flight, compared to a flight in the evening.

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 January 4, 2025.
See what other customers who have flown with Air Canada, United Airlines 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
8,526 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,526 reviews
Delta
8.0
Very good
8,526 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines
7.4
Good
8,963 reviews
Delta
8.0
Very good
8,526 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,526 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air Canada
7.0
Good
8,493 reviews
Delta
8.0
Very good
8,526 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Spirit Airlines
6.3
Okay
8,088 reviews
Delta
8.0
Very good
8,526 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.3

Overall

8.0

Entertainment

7.9

Reviews

1 / 10

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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?

    Frontier, at $384, was found to be the cheapest airline from Chicago O'Hare Intl Airport to Simpson Bay.Alternate airlines to your destination round-trip include Spirit Airlines and Air Canada. These flights start at 49% 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 ($138), Spirit Airlines ($154), and Air Canada ($273).

  • 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 $656, our data shows the cheapest flight currently is $347. When looking at the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana), you can expect to pay $352 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 March 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.

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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 January 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$259Average$441FlexibilityNo cancel feeOn-time65%
DeltaCheapest$554Average$709FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$576Average$728FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$638Average$886FlexibilityNo cancel feeOn-time69%
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