$117 Find Cheap Flights from Chicago to Saint Martin Island - Compare and Save

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 9/27. 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.
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1 adult, Economy, 0 bags

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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, 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
$317JetBlue
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
$325JetBlue
Thu, Sep 24 - Sun, Sep 27
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
$350JetBlue
Sat, Oct 3 - Sat, Oct 17
JetBlue Logo
6:00 am - 2:00 pm
ORD
-
SXM
7h 00m
1 stop
JetBlue Logo
1:45 pm - 11:44 pm
SXM
-
ORD
10h 59m
1 stop
$354JetBlue
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
$377JetBlue
Fri, Aug 14 - Fri, Aug 21
Southwest Logo
5:00 am - 2:05 pm
MDW
-
SXM
8h 05m
1 stop
Southwest Logo
3:05 pm - 10:40 pm
SXM
-
MDW
8h 35m
1 stop
$385Southwest
Fri, Aug 14 - Fri, Aug 21
Southwest Logo
5:00 am - 2:05 pm
MDW
-
SXM
8h 05m
1 stop
Southwest Logo
3:05 pm - 7:35 am
SXM
-
MDW
17h 30m
2 stops
$390Southwest
Sat, Aug 22 - Fri, Aug 28
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
$394JetBlue
Sat, Aug 22 - Wed, Aug 26
JetBlue Logo
6:00 am - 4:19 pm
ORD
-
SXM
9h 19m
1 stop
JetBlue Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$406JetBlue
Thu, Oct 1 - Sun, Oct 4
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
$410JetBlue
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 5 days was to Simpson Bay, at $672 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 5 days was $672.

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 $790 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 $790.

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 $472, 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 June and July, when the average cost of round-trip tickets is $574 and $379 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 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$117
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 13% 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 3 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.
7.8
DeltaOverall score based on 8453 reviews
7.2Food
7.8Comfort
8.1Boarding
7.8Entertainment
8.5Crew
Airline reviews

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

2.0 MediocreJean, Jun 2026
MDW - ATL
Read more Delta reviews

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

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.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

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.

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.