$70 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 4/18. 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, Apr 18 - Sat, Apr 25
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$253Spirit Airlines
Sat, Apr 25 - Sat, May 2
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$270Spirit Airlines
Sat, Apr 25 - Sat, May 2
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$276Spirit Airlines
Sat, Apr 18 - Sat, Apr 25
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$277Spirit Airlines
Sat, Apr 18 - Sat, Apr 25
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$279Spirit Airlines
Sat, Apr 11 - Sat, Apr 18
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$283Spirit Airlines
Sat, Apr 18 - Sun, Apr 26
Multiple Airlines Logo
1:27 pm - 1:37 pm
ORD
-
SXM
23h 10m
1 stop
Multiple Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$304Multiple 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, Apr 26 - Tue, Apr 28
Southwest Logo
5:05 am - 2:25 pm
MDW
-
SXM
8h 20m
1 stop
Southwest Logo
2:25 pm - 7:35 am
SXM
-
MDW
18h 10m
2 stops
$520Southwest
Tue, Apr 28 - Tue, May 5
Southwest Logo
6:00 am - 1:30 pm
MDW
-
SXM
6h 30m
1 stop
Southwest Logo
2:25 pm - 7:35 am
SXM
-
MDW
18h 10m
2 stops
$552Southwest
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 $660 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 $660.

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 $786 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 $786.

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 $433, 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 $440 (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 $782 respectively.

What’s the cheapest day of the week to fly from Chicago to Saint Martin Island?

The average price of all round-trip flights from Chicago to Saint Martin Island clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Saint Martin Island, you should consider leaving on a Sunday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Mondays and the most expensive ones on Saturdays.

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 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$70
Best time to beat the crowds with an average 34% 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

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 8367 reviews
7.9Comfort
7.2Food
8.1Boarding
8.5Crew
7.8Entertainment
Airline reviews

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

10.0 ExcellentLorna, Mar 2026
LAX - PDX
Read more Delta reviews

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Staff at the check-in counter were friendly, happy and helpful. They tagged our bags and sent us to “bag drop off” but were not very clear about where that was. The airport was busy we headed off in what we thought was the right direction until a gentleman waved us down and actually came after us. He was the baggage handler for Delta and recognized our “deer in the headlights “ look-he brought us to the right area (which was marked as the Southwest Airlines Drop Off) and sent us on our way. Wonderful guy, low key and working with a big smile on his face. Loved it. Loved him.

During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta. The airline did not hold the connection, and we were informed that the next available flight is not for another 24 hours. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for us as a resident of New Jersey.

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

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.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

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.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

They keep delaying and cancel at last moment and height was for you to get refund need to be in chat line for two hours. I complained to DOT. Never recommend this airline on Kayak please

First flight in along time with spirit! I’m honored to say this flight was excellent 😊

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Every connection was late but that meant I was not running from one to the next so that was a good thing. No one wants to miss a connection

Food and entertainment see irrelevant to rate them as that’s not really an option anymore. The flight was fast and friendly. The plane was immaculately clean.

it was great except the extra charges. for carry on ,seat choice, and wifi. these should all be included in flight charge. The extra charges are redicuolouse and because of that I will not be flying spirit again

Nothing. We didn’t even have a pilot until one hour after our flight was set to depart and now we are waiting for a gate on a very hot packed aircraft. Spirit has lost its goddamn minds and we will never fly again. On the way down the delay went from 5 minutes to 6 hours to cancelled.

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.