ORD - SXM

$150 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 9/10. 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
1 adult, Economy, 0 bags

KAYAK searches 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

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

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

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

Everything you should know

Cheapest round-trip
$365
Typical prices: $637-$321
JetBlue
Fri 9/18Fri 9/25
ORD - SXM • 1 stop
Cheapest non-stop
$695
American Airlines
Sat 12/5Sat 12/12
ORD - SXM • Non-stop
Top airlines
Cheapest • from $365 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $594 (round-trip)
Shortest trip • 7h 10m (one-way)
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 79% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 32% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 44% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to Simpson Bay

Fri, Sep 18 - Fri, Sep 25
JetBlue Logo
6:00 am - 2:00 pm
ORD
-
SXM
7h 00m
1 stop
JetBlue Logo
3:05 pm - 11:31 pm
SXM
-
ORD
9h 26m
1 stop
$365JetBlue
Thu, Sep 10 - Mon, Sep 14
JetBlue Logo
6:00 am - 2:00 pm
ORD
-
SXM
7h 00m
1 stop
JetBlue Logo
3:05 pm - 11:31 pm
SXM
-
ORD
9h 26m
1 stop
$384JetBlue
Sat, Sep 12 - Sat, Sep 19
JetBlue Logo
6:00 am - 2:00 pm
ORD
-
SXM
7h 00m
1 stop
JetBlue Logo
3:05 pm - 11:31 pm
SXM
-
ORD
9h 26m
1 stop
$389JetBlue
Fri, Jul 3 - Thu, Jul 9
Multiple Airlines Logo
2:15 pm - 5:00 pm
ORD
-
SXM
25h 45m
1 stop
Multiple Airlines Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$403Multiple Airlines
Sat, Aug 15 - Sat, Aug 22
JetBlue Logo
6:00 am - 4:16 pm
ORD
-
SXM
9h 16m
1 stop
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$426JetBlue
Wed, Sep 16 - Sat, Sep 19
JetBlue Logo
3:00 pm - 2:00 pm
ORD
-
SXM
22h 00m
1 stop
JetBlue Logo
3:05 pm - 11:31 pm
SXM
-
ORD
9h 26m
1 stop
$433JetBlue
Fri, Jul 3 - Thu, Jul 9
JetBlue Logo
5:22 pm - 10:05 am
ORD
-
SXM
15h 43m
1 stop
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$437JetBlue
Sat, Aug 22 - Sat, Aug 29
JetBlue Logo
6:00 am - 4:16 pm
ORD
-
SXM
9h 16m
1 stop
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$446JetBlue
Tue, Jul 7 - Tue, Jul 14
JetBlue Logo
6:30 pm - 10:07 am
ORD
-
SXM
14h 37m
1 stop
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$452JetBlue
Fri, Jul 3 - Thu, Jul 9
JetBlue Logo
5:22 pm - 4:17 pm
ORD
-
SXM
21h 55m
1 stop
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$453JetBlue
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Simpson Bay flights

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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Simpson Bay?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Simpson Bay departing in September.

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 round-trip 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 $364 (return) on average. On the other hand, the most expensive months are July and April, where the average cost of round-trip tickets is $770 and $767 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Simpson Bay?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $736 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Simpson Bay, you should book around 4 weeks before departure, which saves you about 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$150
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 12% 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 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Simpson Bay was $150 for a one-way ticket and $365 for a round-trip.

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

    Yes

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to Simpson Bay?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago O'Hare Airport to Simpson Bay flight route.

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

    The Boeing 737 MAX 8 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?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago O'Hare Airport and Simpson Bay, with SkyTeam being the most commonly used for this route.

  • 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 $392 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $757 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.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Simpson Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for $700 or less round-trip.

Reviews of the top 5 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.
7.9
DeltaOverall score based on 8400 reviews
7.8Entertainment
7.2Food
7.8Comfort
8.1Boarding
8.5Crew
Airline reviews

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

4.0 OkayMichelle, Jun 2026
ATL - PIT
Read more Delta reviews

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

It was pretty straight forward, no glitches or hidden costs

It was a short flight so, everything went smoothly and we got to where we needed to be safely.

Didn’t make it on the flight. Delayed then had to be rebooked, which in turn had me waiting at the airport for another 8 hours before next flight

No TV on the flight. The charging outlet was not working. No food, even a sandwich. The served orange was poor quality.

Selected seats 5 months prior to date. Had email confirmation and seats were not honoured. Family did not sit together

Loved and was pleasantly surprised by the food!! Request Lufthansa to help transiting passengers at Munich (confusion whether to go thru passport control or not).

The flight was comfortable and the staff were helpful and friendly. However, we did not know we were flying PAL until we arrived in Canada, so it was a bit disconcerting. In addition, which port we were leaving from was confusing.

They did not let us board because one member needed a transit visa, which was not evident at the time of ticket purchase.

I was charge a baggage checking fee $68!! I volunteered to check my duffle bag which usually goes under my seat!

I did not like anything because the flight was cancelled yesterday and I did not get to arrive on time in Toronto as I was rebooked with another airline. This caused me to be really stressed out as I am an individual with back injury and to be forced to stay longer in an airport to accommodate a change of airline and the transfers associated with it Due to this I am probably not going to book through your website to eliminate this potentially chaos in the future

Nice plane, clean, wifi available and movies. All the flight attendants were courteous.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

The flight was delayed for more than 3 hours the flight attendant was so angry, it was my first flight with JetBlue but i don’t think I flight with them again.

First the flt was delayed over 2 hrs bc of plane mechanics that should have been handled better! No text or email was sent so only found out at the airport so there we sat for 5 hours! THATS RIDICULOUS! The gate area was filthy! No agents showed up till hr before so no additional info was given-waited online for 15 mins while the gate agent chatted and got together then given last seat in back of plane!! No priority for senior or anything-took attendants over 2hrs to serve drinks and snack-WHY are they not served together? By time snack came needed another drink! Worst service in my life!

Since we started at syr the service, crews, and flights were just excellent

All the TV screens in my rows was non functional . The map shown for an international route was antiqued..

It was fine for what it was. It’s not luxury travel but it was efficient, for the most part. Having my carry-on transferred into luggage however, was unwelcome.

We had better-than-average leg room and I loved the access to shows and movies. During boarding, we could not hear the agent even though we were close to the boarding door, which was kind of scary when we realized that half of the passengers had already boarded. Also, the entertainment was awesome, but I could not hear the movie as well as I would have liked, because my headphones were crappy. It would have been better if I could connect my own ear buds via Bluetooth or if JetBlue provided headphones.

On time, friendly attendants, quick wheelchair assistance and help checking in bags. Also appreciated change in seats, more forward to make it easier for my 97 year old mother to board and exit the plane. Thank you, JetBlue!

Flight did not have onboard charging and TV screen flickering.

Everything you need to know for your flight from O'Hare Intl to Simpson Bay

Information on your arrival and departure airports