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ORD - SXM

$120 Find cheap flights from Chicago O'Hare Airport to Simpson Bay

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Simpson Bay departing on 6/4. 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 5/30
Thu 6/6

Search hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Simpson Bay, 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 Chicago to Simpson Bay, as well as popular online travel agencies
In the last 7 days travelers have searched 43,983,279 times on KAYAK, and here is why:

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Simpson Bay 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
5:56 pm - 3:07 pmORD-SXM
20h 11m1 stop
4:14 pm - 12:58 amSXM-ORD
9h 44m1 stop
$179Frontier
Find Deal
Sat, May 18 - Sat, May 25
5:56 pm - 3:07 pmORD-SXM
20h 11m1 stop
4:27 pm - 12:58 amSXM-ORD
9h 31m1 stop
$192Frontier
Find Deal
Sat, May 25 - Sat, Jun 1
5:00 am - 1:44 pmORD-SXM
7h 44m1 stop
2:44 pm - 5:40 pmSXM-ORD
27h 56m1 stop
$300Spirit Airlines
Find Deal
Wed, May 15 - Mon, May 20
5:00 am - 1:44 pmORD-SXM
7h 44m1 stop
2:44 pm - 12:55 amSXM-ORD
11h 11m1 stop
$319Spirit Airlines
Find Deal
Wed, May 29 - Fri, Jun 7
7:30 pm - 1:55 pmORD-SXM
17h 25m2 stops
3:20 pm - 9:21 amSXM-ORD
19h 01m2 stops
$559Delta
Find Deal
Mon, Jun 24 - Wed, Jul 3
5:15 am - 3:05 pmORD-SXM
8h 50m2 stops
2:12 pm - 9:29 pmSXM-ORD
8h 17m1 stop
$581American Airlines
Find Deal
Wed, May 29 - Sun, Jun 2
5:15 am - 3:05 pmORD-SXM
8h 50m2 stops
4:05 pm - 7:25 amSXM-ORD
16h 20m2 stops
$583American Airlines
Find Deal
Wed, May 29 - Sun, Jun 2
7:29 pm - 1:49 pmORD-SXM
17h 20m2 stops
3:19 pm - 9:27 amSXM-ORD
19h 08m2 stops
$584Delta
Find Deal
Tue, Jul 23 - Sat, Aug 17
10:43 am - 4:49 pmORD-SXM
5h 06mnonstop
1:30 pm - 6:14 pmSXM-ORD
5h 44mnonstop
$590United Airlines
Find Deal
Sat, Jul 6 - Sat, Jul 13
10:43 am - 4:49 pmORD-SXM
5h 06mnonstop
1:30 pm - 6:14 pmSXM-ORD
5h 44mnonstop
$635United Airlines
Find Deal
Sat, May 25 - Sat, Jun 1

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

Get data-powered insights and trends into flights from O'Hare Intl to Simpson Bay 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 Chicago O'Hare Airport to Simpson Bay?

The average price of all flights from Chicago O'Hare Intl Airport to Simpson Bay clicked on KAYAK for each day over the last 12 months.
For Chicago O'Hare Airport to Simpson Bay, Wednesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Simpson Bay back to Chicago O'Hare Airport, the best deals are generally found on Monday, with Sunday being the most expensive.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago O'Hare Intl Airport to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago O'Hare Intl Airport to Simpson Bay is September, where tickets cost $648 on average. On the other hand, the most expensive months are March and July, where the average cost of tickets is $1,026 and $1,017 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Simpson Bay?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago O'Hare Intl Airport to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago O'Hare Intl Airport to Simpson Bay, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 23 days before departure.

Which airlines fly non-stop between Chicago O'Hare Intl Airport and Simpson Bay?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago O'Hare Intl Airport to Simpson Bay.
There is just one airline that flies from Chicago O'Hare Intl Airport to Simpson Bay direct and that is United Airlines. The best one-way deal found from United Airlines for the route is $438.

How many flights are there between Chicago O'Hare Intl Airport and Simpson Bay per day?

There is a maximum of 1 nonstop flight a day that takes off from Chicago O'Hare Intl Airport and lands in Simpson Bay, with an average flight time of 5h 06m. The most common departure time is 10:00 am and most flights take off in the morning. Each week, there are 1 flights.

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

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.

How long does a flight from Chicago O'Hare Airport to Simpson Bay take?

Direct flights take on average 5h 06m to travel the 2,204 miles between Chicago O'Hare Airport and Simpson Bay.

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

Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 10:43 am and will be landing in Simpson Bay at 4:49 pm.

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

If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to Simpson Bay jets off at 10:43 am and lands at 4:49 pm.

Good to know

Low season

July

High season

February

Cheapest flight

$120
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Chicago O'Hare Airport to Simpson Bay

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

Are your dates flexible? Find out the best times to travel from O'Hare Intl to Simpson Bay 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 Chicago O'Hare Airport to Simpson Bay flights

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

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Simpson Bay was $120 for a one-way ticket and $179 for a round-trip.

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

    Yes

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

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

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

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

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

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

  • Which is the best airline for flights from Chicago to Simpson Bay, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Simpson Bay are Delta and United Airlines. With an average price for the route of $709 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $895 and an overall rating of 7.4.

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

    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 Chicago O'Hare Airport to Simpson Bay.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Chicago O'Hare Airport 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 Chicago O'Hare Airport to Simpson Bay?

    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 Simpson Bay with an airline and back to Chicago O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and SXM 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 Chicago O'Hare Airport to Simpson Bay?

    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 Simpson Bay from Chicago O'Hare Airport 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 ORD to Simpson Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for $451 or less one-way and $602 or less round-trip.

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

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

Nonstop departures

Chicago O'Hare Intl to Simpson Bay Princess Juliana

Saturday

United Airlines

United Airlines

See more direct flights

Nonstop returns

Simpson Bay Princess Juliana to Chicago O'Hare Intl

Saturday

United Airlines

United Airlines

See more direct flights
See more direct flights

Top 4 airlines serving from O'Hare Intl to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Simpson Bay. 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 O'Hare Intl to Simpson Bay? 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.
8.0
DeltaOverall score based on 10913 reviews
8.2Boarding
7.9Comfort
8.0Entertainment
8.6Crew
7.4Food
Airline reviews

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

8.0 ExcellentCynthia, Apr 2024ATL - SJD
Read more about Delta reviews

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Baggage claim took too long and priority bags were not delivered first.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

Book cheap flights from Chicago to Simpson Bay

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Simpson Bay found on KAYAK in the last 72 hours.
6/4Tue
2 stopsSpirit Airlines
27h 13mORD-SXM
$120
6/4Tue
1 stopSpirit Airlines
18h 08mORD-SXM
$121
5/22Wed
1 stopSpirit Airlines
7h 44mORD-SXM
$139
6/4Tue
3 stopsSpirit Airlines
19h 12mORD-SXM
$147
5/22Wed
2 stops
37h 12mORD-SXM
$182
5/22Wed
3 stopsSpirit Airlines
40h 35mORD-SXM
$255

Search by stops

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Last minute flights from O'Hare Intl to Simpson Bay

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 Chicago to Simpson Bay that are departing in the next 10 days.
5/3Fri
multi-stop
15h 22mORD-SXM
5/5Sun
multi-stop
23h 34mSXM-ORD
$802
5/3Fri
multi-stop
15h 22mORD-SXM
5/5Sun
multi-stop
21h 39mSXM-ORD
$817
5/4Sat
multi-stopAmerican Airlines
18h 01mORD-SXM
5/7Tue
multi-stopAmerican Airlines
8h 17mSXM-ORD
$912
5/3Fri
multi-stop
20h 54mORD-SXM
5/5Sun
multi-stop
27h 35mSXM-ORD
$913
5/4Sat
multi-stopAmerican Airlines
18h 01mORD-SXM
5/7Tue
multi-stopAmerican Airlines
12h 24mSXM-ORD
$916
5/4Sat
multi-stopAmerican Airlines
14h 10mORD-SXM
5/7Tue
multi-stopAmerican Airlines
12h 24mSXM-ORD
$918
5/3Fri
multi-stop
30h 38mORD-SXM
5/5Sun
multi-stop
27h 35mSXM-ORD
$941
5/2Thu
multi-stopAmerican Airlines
7h 01mORD-SXM
5/5Sun
multi-stopAmerican Airlines
8h 37mSXM-ORD
$972
5/2Thu
multi-stopAmerican Airlines
7h 01mORD-SXM
5/5Sun
multi-stopAmerican Airlines
10h 28mSXM-ORD
$976
5/3Fri
multi-stop
30h 38mORD-SXM
5/5Sun
multi-stop
32h 33mSXM-ORD
$1,000

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Chicago O'Hare Airport - Simpson Bay Flights

Departure:

Chicago O'Hare Airport (ORD)United States

Destination:

Simpson Bay (SXM)St. Maarten

Return flight deals:

Simpson Bay - Chicago O'Hare Airport

Cabin classes:

$2,453
$2,013
$577