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SXM - ORD

Find cheap flights from Simpson Bay to Chicago O'Hare Airport from $373

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Simpson Bay to O'Hare Intl departing on 7/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Thu 5/23
Thu 5/30

Search hundreds of travel sites at once for deals on flights to Chicago O'Hare Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Simpson Bay to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Simpson Bay to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 44,632,927 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Simpson Bay to O'Hare Intl (SXM-ORD)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Simpson Bay to O'Hare Intl that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
4:14 pm - 12:58 amSXM-ORD
9h 44m1 stop
5:00 am - 1:44 pmORD-SXM
7h 44m1 stop
Sat, May 18 - Sat, Aug 17
2:44 pm - 12:00 amSXM-ORD
10h 16m1 stop
5:00 am - 1:44 pmORD-SXM
7h 44m1 stop
$466Spirit Airlines
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Fri, Oct 4 - Fri, Oct 18
2:44 pm - 11:29 pmSXM-ORD
9h 45m1 stop
6:00 am - 7:40 pmORD-SXM
12h 40m2 stops
Sat, May 18 - Sat, Aug 17
2:44 pm - 12:00 amSXM-ORD
10h 16m1 stop
5:00 am - 1:44 pmORD-SXM
7h 44m1 stop
$539Spirit Airlines
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Sat, Oct 5 - Sat, Oct 19
3:19 pm - 8:22 amSXM-ORD
18h 03m1 stop
7:55 pm - 1:49 pmORD-SXM
16h 54m1 stop
$546Delta
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Fri, Oct 4 - Sun, Oct 20
3:19 pm - 10:10 amSXM-ORD
19h 51m1 stop
7:55 pm - 1:49 pmORD-SXM
16h 54m1 stop
$571Delta
Find Deal
Sat, Oct 5 - Sun, Oct 20
2:10 pm - 9:21 pmSXM-ORD
8h 11m1 stop
5:28 am - 1:13 pmORD-SXM
6h 45m1 stop
$577American Airlines
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Fri, Jul 12 - Thu, Jul 25
2:42 pm - 7:28 amSXM-ORD
17h 46m2 stops
8:20 pm - 1:22 pmORD-SXM
16h 02m1 stop
$586American Airlines
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Thu, Oct 3 - Sat, Oct 19
3:55 pm - 11:30 pmSXM-ORD
8h 35m1 stop
10:43 am - 4:49 pmORD-SXM
5h 06mnonstop
$645United Airlines
Find Deal
Sat, May 18 - Sat, Aug 17
4:04 pm - 12:59 amSXM-ORD
9h 55m2 stops
7:15 pm - 2:31 pmORD-SXM
18h 16m2 stops
$681Frontier
Find Deal
Fri, Jul 12 - Thu, Jul 25

Flights from Simpson Bay to O'Hare Intl - Travel Insights & Trends

Get data-powered insights and trends into flights from Simpson Bay to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Simpson Bay to Chicago O'Hare Airport?

The average price of all flights from Simpson Bay to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Simpson Bay to Chicago O'Hare Airport, look for departures on Mondays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago O'Hare Airport, Wednesday is the cheapest day to fly and Saturday is the most expensive.

Which airlines provide the cheapest flights from Simpson Bay to Chicago O'Hare Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Simpson Bay to Chicago O'Hare Airport found on KAYAK was with United Airlines for $373. Spirit Airlines proposed a round-trip connection from $466 and Delta from $546.

Which cabin class options are there for flights between Simpson Bay and Chicago O'Hare Intl Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 3 cabin class options for the route. These are Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from Simpson Bay to Chicago O'Hare Airport?

Early birds can take the earliest flight from Simpson Bay at 1:30 pm and will be landing in Chicago O'Hare Intl Airport at 6:14 pm.

What’s the latest departure time from Simpson Bay to Chicago O'Hare Airport?

If you prefer to fly at night, the latest flight from Simpson Bay to Chicago O'Hare Intl Airport jets off at 1:30 pm and lands at 6:14 pm.

Good to know

Low season

November

High season

March

Cheapest flight

$373
Best time to beat the crowds with an average 61% drop in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Simpson Bay to Chicago O'Hare Airport

When to book flights from Simpson Bay to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Simpson Bay to O'Hare Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Simpson Bay to Chicago O'Hare Airport flights

  • What is the cheapest flight from Simpson Bay to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Simpson Bay to Chicago O'Hare Intl Airport was $373 for a one-way ticket and $400 for a round-trip.

  • Do I need a passport to fly between Simpson Bay and Chicago O'Hare Airport?

    A passport is required to fly from Simpson Bay to Chicago O'Hare Airport.

  • Which airports will I be using when flying from Simpson Bay to Chicago O'Hare Airport?

    Simpson Bay airport is called Simpson Bay Princess Juliana and the only airport in Chicago O'Hare Airport is Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Simpson Bay to Chicago O'Hare Airport?

    The Boeing 737-700 is the aircraft model that flies most regularly on the Simpson Bay to Chicago O'Hare Airport flight route.

  • Which airline alliances offer flights from Simpson Bay to Chicago O'Hare Airport?

    Star Alliance is the only airline alliance operating flights between Simpson Bay and Chicago O'Hare Airport.

  • On which days can I fly direct from Simpson Bay to Chicago O'Hare Airport?

    You can catch a nonstop flight from Simpson Bay to Chicago O'Hare Airport on Saturday.

  • How does KAYAK find such low prices on flights from Simpson Bay to Chicago O'Hare Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Simpson Bay to Chicago O'Hare Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Simpson Bay to Chicago O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from Simpson Bay is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Simpson Bay to Chicago O'Hare Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago O'Hare Airport with an airline and back to Simpson Bay with another airline. Booking your flights between Simpson Bay and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Simpson Bay to Chicago O'Hare Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago O'Hare Airport from Simpson Bay up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from SXM to Chicago O'Hare Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $395 or less one-way and $357 or less round-trip.

Prefer to fly non-stop from Simpson Bay to Chicago O'Hare Airport?

Find which airlines fly direct from Princess Juliana to O'Hare Intl, which days they fly and book direct flights.

Nonstop departures

Simpson Bay Princess Juliana to Chicago O'Hare Intl

Saturday

United Airlines

United Airlines

See more direct flights

Nonstop returns

Chicago O'Hare Intl to Simpson Bay Princess Juliana

Saturday

United Airlines

United Airlines

See more direct flights
See more direct flights

Top airline flying from Simpson Bay to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Simpson Bay to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Simpson Bay to O'Hare Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
American AirlinesOverall score based on 14914 reviews
7.1entertainment
7.2comfort
8.0crew
7.6boarding
6.6food
Airline reviews

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

6.0 GoodAnonymous, Apr 2024SPI - ORD
Read more about American Airlines reviews

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Book cheap flights from Simpson Bay to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Simpson Bay to Chicago found on KAYAK in the last 72 hours.
7/20Sat
nonstopUnited Airlines
5h 44mSXM-ORD
$373
7/20Sat
1 stopSpirit Airlines
9h 39mSXM-ORD
$380
7/20Sat
2 stopsAmerican Airlines
18h 58mSXM-ORD
$453
4/28Sun
3 stops
48h 58mSXM-ORD
$529
4/28Sun
2 stops
48h 58mSXM-ORD
$562
4/28Sun
1 stopAmerican Airlines
9h 57mSXM-ORD
$568

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Last minute flights from Simpson Bay to O'Hare Intl

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Simpson Bay to Chicago that are departing in the next 10 days.
4/26Fri
multi-stopSpirit Airlines
10h 36mSXM-ORD
4/29Mon
multi-stopSpirit Airlines
7h 47mORD-SXM
$548
4/26Fri
multi-stopSpirit Airlines
10h 36mSXM-ORD
4/29Mon
multi-stopSpirit Airlines
7h 47mORD-SXM
$568
4/26Fri
multi-stopAmerican Airlines
19h 26mSXM-ORD
4/29Mon
multi-stopAmerican Airlines
7h 01mORD-SXM
$1,001

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Simpson Bay - Chicago O'Hare Airport Flights

Departure:

Simpson Bay (SXM)St. Maarten

Destination:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Chicago O'Hare Airport - Simpson Bay

Cabin classes:

$965
$357