HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
O'Hare Intl

$345+ Cheap flights from Simpson Bay (SXM) to O'Hare Intl (ORD)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — ORD
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Simpson Bay to O'Hare Intl 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.

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 April 30, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$345
(Flightnetwork)

Good one-way deal

$574 or less
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago O'Hare Intl flights.
Search Deals
From Simpson Bay Princess Juliana to Chicago O'Hare Intl
Search Deals
Price to beat on a one-way flight from Simpson Bay Princess Juliana to Chicago O'Hare Intl.
Search Deals

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 April 30, 2025.

This Flightnetwork deal was found by Cheapflights users on 4/29. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/303:05 pmSXM - ORD
1 stop10h 00mMultiple Airlines
Fri 6/65:08 pmORD - SXM
1 stop17h 15mMultiple Airlines
Deal found 4/29$345
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/303:05 pmSXM - ORD
1 stop10h 00mSpirit Airlines
Fri 6/64:35 pmORD - SXM
2 stops20h 25mSpirit Airlines
Deal found 4/29$417
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/92:40 pmSXM - ORD
1 stop8h 54mAmerican Airlines
Wed 10/156:00 amORD - SXM
1 stop8h 10mAmerican Airlines
Deal found 4/29$623

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 April 30, 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 5/30

3:05 pm-12:05 am

1 stop10h 00m

Chicago O'Hare Intl

Fri 6/6

5:08 pm-11:23 am

1 stop17h 15m

$345

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 5/30

3:05 pm-12:05 am

1 stop10h 00m

Chicago O'Hare Intl

Fri 6/6

4:35 pm-2:00 pm

2 stops20h 25m

$417

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 10/9

2:40 pm-10:34 pm

1 stop8h 54m

Chicago O'Hare Intl

Wed 10/15

6:00 am-3:10 pm

1 stop8h 10m

$623

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
AranGrantPrice 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 Simpson Bay-Chicago O'Hare Intl Airport flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Simpson Bay-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 April 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Simpson Bay to Chicago O'Hare Intl Airport in the morning. If you’re flexible enough to do this you can expect to save up to 39% on your trip compared to booking a flight at noon.

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated April 30, 2025.
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.5

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2025

MYR - CLT

This flight was impacted by a nearly 4, yes 4 hour delay. They replaced a 777 with another one and it had to be cleaned and catered before we could depart. Great crew did it without complaint.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.5

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2025

MYR - CLT

This flight was impacted by a nearly 4, yes 4 hour delay. They replaced a 777 with another one and it had to be cleaned and catered before we could depart. Great crew did it without complaint.
Spirit Airlines
6.3
Okay
7,956 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.5

Comfort

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2025

MYR - CLT

This flight was impacted by a nearly 4, yes 4 hour delay. They replaced a 777 with another one and it had to be cleaned and catered before we could depart. Great crew did it without complaint.

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 1 airline. Simpson Bay Princess Juliana is conveniently located just 0.5 mi from Simpson Bay’s city center.

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

    Cheapflights users have booked flights from Simpson Bay to Chicago O'Hare Intl Airport round-trip from $417. Another airline that can offer you cheap pricing is American Airlines.

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

    On average you can expect to pay $605 for a flight from Simpson Bay to Chicago O'Hare Intl Airport. The cheapest flight overall is $538 while the most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl) is currently priced at $348.

  • 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 Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Schaumburg
Hoffman Estates
Rosemont
Beloit
Racine
Skokie
Naperville
Elgin
Tinley Park
Kenosha
Rockford
Arlington Heights
Orland Park
Joliet
Merrillville
Northbrook
Glenview
Des Plaines
Lake Geneva
Waukegan

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 Simpson Bay to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
Simpson Bay to Midway flights

Top airline flying from Simpson Bay to O'Hare Intl

Discover the top airline that operate flights from Simpson Bay to O'Hare Intl. 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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$554Average$680FlexibilityNo cancel feeOn-time71%

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.