$166 Find Cheap Flights from Chicago to Saint Martin Island

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Saint Martin Island departing on 6/19. 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 Saint Martin Island

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Saint Martin Island, 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 Saint Martin Island, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% 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.

Flight Deals
Booking Insights
Flight Deals

Book Cheap Chicago to Saint Martin Island Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Saint Martin Island 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 Chicago to Saint Martin Island

Fri, Jun 12 - Sat, Jun 20
Air Canada Logo
9:55 am - 5:00 pm
ORD
-
SXM
30h 05m
1 stop
Air Canada Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
$380Air Canada
Fri, Jun 12 - Sat, Jun 20
Air Canada Logo
6:22 pm - 5:00 pm
ORD
-
SXM
21h 38m
2 stops
Air Canada Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
$391Air Canada
Fri, Jul 24 - Thu, Aug 20
Multiple Airlines Logo
5:35 pm - 5:00 pm
ORD
-
SXM
22h 25m
1 stop
Multiple Airlines Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$395Multiple Airlines
Fri, Jul 10 - Thu, Jul 16
Multiple Airlines Logo
8:40 pm - 5:00 pm
ORD
-
SXM
19h 20m
1 stop
Multiple Airlines Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$404Multiple Airlines
Tue, Sep 1 - Wed, Sep 2
JetBlue Logo
6:27 pm - 10:02 am
ORD
-
SXM
14h 35m
1 stop
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$405JetBlue
Sat, Aug 29 - Tue, Sep 1
JetBlue Logo
7:00 am - 12:37 pm
ORD
-
SXM
28h 37m
1 stop
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$408JetBlue
Fri, Jul 10 - Thu, Jul 16
Multiple Airlines Logo
8:40 pm - 5:00 pm
ORD
-
SXM
19h 20m
1 stop
Multiple Airlines Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$418Multiple Airlines
Sat, Jul 4 - Thu, Jul 9
JetBlue Logo
6:00 am - 4:17 pm
ORD
-
SXM
9h 17m
1 stop
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$421JetBlue
Mon, Aug 3 - Mon, Aug 17
Southwest Logo
5:10 am - 1:25 pm
MDW
-
SXM
7h 15m
1 stop
Southwest Logo
3:05 pm - 10:40 pm
SXM
-
MDW
8h 35m
1 stop
$541Southwest
Fri, Jul 10 - Thu, Jul 16
Southwest Logo
5:10 am - 1:25 pm
MDW
-
SXM
7h 15m
1 stop
Southwest Logo
2:25 pm - 12:45 am
SXM
-
MDW
11h 20m
1 stop
$551Southwest
Booking Insights

KAYAK's insights & trends for Chicago to Saint Martin Island flights

Get data-powered insights and trends into flights from Chicago to Saint Martin Island to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Saint Martin Island flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Saint Martin Island from Chicago found in the last 7 days was to Simpson Bay, at $482 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Simpson Bay (SXM), and the cheapest round-trip airline ticket found on this route in the last 7 days was $482.

What is the cheapest time of day to fly to Saint Martin Island?

The average price for all round-trip flights from Chicago to Saint Martin Island depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Saint Martin Island is generally in the morning, when round-trip flights cost $777 on average. The most expensive time of day to fly to Saint Martin Island is generally in the morning, which is peak travel time and where the average cost of a ticket is $777.

Can I save money by flying with a layover from Chicago to Saint Martin Island?

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.

No, with an average price for the route of $460, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Saint Martin Island?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Saint Martin Island, 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 to Saint Martin Island is February, when tickets cost $74 (return) on average. On the other hand, the most expensive months are July and May, when the average cost of round-trip tickets is $376 and $340 respectively.

How far in advance should I book a flight from Chicago to Saint Martin Island?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Saint Martin Island, 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 to Saint Martin Island, 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 seasonSeptember
Cheapest flight$166
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Chicago O'Hare Airport to Simpson Bay

FAQs - booking Saint Martin Island flights

  • How does KAYAK find such low prices on flights from Chicago to Saint Martin Island?

    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 to Saint Martin Island.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Saint Martin Island?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Saint Martin Island 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 to Saint Martin Island?

    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 from Chicago to Saint Martin Island with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Saint Martin Island?

    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 from Chicago to Saint Martin Island up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Chicago to Saint Martin Island

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Saint Martin Island. 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 Chicago to Saint Martin Island? 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 8422 reviews
8.5Crew
7.8Comfort
8.1Boarding
7.2Food
7.8Entertainment
Airline reviews

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

6.0 GoodAnonymous, May 2026
ATL - ECP
Read more Delta reviews

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

Clean planes and not take my comfort class seat away.

The crew were efficient. The pilots seemed professional. It was a bit chilly in our seats. The sheet provided weren’t very helpful.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

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.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

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.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

My flight today was cancelled because it was Spirit Airlines but have received no refund.

THEY WENT OUT OF BUSINESS AND CANCELED FLIGHT. REPLACEMENT FLIGHTS WERE 300% HIGHER SO MY FAMILY COULD NOT GET TOGETHER. WHY AM I GETTING THIS SURVEY?????

If there WAS a flight it would have been EXCELENT..Maybe?

It would have been better IF IT HAD NOT BEEN CANCELED!!!!

The airline cancel mi flight, lost a lot of money!!!

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Everything you need to know for your flight to Saint Martin Island

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.