$82 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 5/3. 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
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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

Sat, May 2 - Sat, May 9
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
$253Spirit Airlines
Sat, May 2 - Thu, May 14
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
$256Spirit Airlines
Sat, May 2 - Sat, May 9
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
$262Spirit Airlines
Sat, May 2 - Sat, May 9
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
$263Spirit Airlines
Sun, May 3 - Thu, May 7
Multiple Airlines Logo
5:05 am - 1:37 pm
ORD
-
SXM
7h 32m
1 stop
Multiple Airlines Logo
2:35 pm - 11:38 pm
SXM
-
ORD
10h 03m
1 stop
$266Multiple Airlines
Sat, May 2 - Sat, May 9
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
$271Spirit Airlines
Sun, May 3 - Thu, May 7
Spirit Airlines Logo
5:05 am - 1:37 pm
ORD
-
SXM
7h 32m
1 stop
Spirit Airlines Logo
2:35 pm - 11:15 pm
SXM
-
ORD
9h 40m
1 stop
$278Spirit Airlines
Sun, May 3 - Thu, May 7
Southwest Logo
5:05 am - 2:25 pm
MDW
-
SXM
8h 20m
1 stop
Southwest Logo
2:25 pm - 12:15 am
SXM
-
MDW
10h 50m
1 stop
$515Southwest
Sun, May 3 - Thu, May 7
Southwest Logo
8:55 pm - 1:30 pm
MDW
-
SXM
15h 35m
2 stops
Southwest Logo
2:25 pm - 12:45 pm
SXM
-
MDW
23h 20m
2 stops
$520Southwest
Mon, May 11 - Mon, May 18
Southwest Logo
5:35 am - 1:30 pm
MDW
-
SXM
6h 55m
1 stop
Southwest Logo
2:25 pm - 12:15 am
SXM
-
MDW
10h 50m
1 stop
$590Southwest
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 72 hours was to Simpson Bay, at $737 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 72 hours was $737.

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 $775 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 $775.

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 $442, 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 September, when tickets cost $427 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $797 and $787 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 31% 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$82
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 8% 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 8405 reviews
8.5Crew
7.2Food
7.8Entertainment
8.1Boarding
7.9Comfort
Airline reviews

The tray table was broken and the food was terrible.

4.0 OkayJeremy, Apr 2026
BNA - BOS
Read more Delta reviews

The tray table was broken and the food was terrible.

The gentleman at the gate I think his name is RIE was exceptional

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

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!!

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

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

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

The flight was delayed four times and finally cancelled. The hotel night we paid for and the connecting flight did not happen. There were also additional costs due to the extra night in Miami. I do not recommend this airline.

The repeated flight delays—this time nearly three hours without any weather-related cause—are unacceptable. Yet, passengers are penalized heavily even for being a minute late. It is unreasonable that there is no compensation for such significant delays, nor even basic provisions like water during the wait or in flight. This imbalance in accountability is deeply frustrating and needs to be addressed.

My flight with spirit airlines was canceled leaving me stranded until tomorrow.

My flight was delayed then put back on time then cancelled and they automatically rebooked me to another flight but that flight was going to make me late to a concert i had planned for. Flight was at 10am concert was at 7pm from Burbank to Las Vegas so I allowed enough time but the flight that was rebooked was too late so I talked with the desk and they were able to get me on an afternoon flight. Thank goodness. That was stressful for a moment. I want to thank the person who helped me get to my show on time. Concert tickets are very expensive and the show was amazing. Hopefully my flight home will be smooth.

Unfortunately Stuff and the stuff boarded us were so rude to many of passengers.i will never fly Spirit again .

Always Good ,… Spirit customers are high class Delta customers are self proclaimed elites and American crews you can hear them complain about everything (they’re loud)

Very nice. Although, it would be nice to offer a glass of water for free. At least.....

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.

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.