$146 Find Cheap Flights from Chicago to St. Maarten - 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 St. Maarten departing on 9/13. 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

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Flight Deals

Book Cheap Chicago to St. Maarten 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 St. Maarten 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 St. Maarten

Mon, Sep 14 - Fri, Sep 18
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
Thu, Sep 10 - Mon, Sep 21
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
$399JetBlue
Thu, Sep 24 - Thu, Oct 1
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
$423JetBlue
Fri, Jul 10 - Fri, Jul 17
Multiple Airlines Logo
5:13 pm - 11:30 am
ORD
-
SXM
17h 17m
1 stop
Multiple Airlines Logo
1:42 pm - 11:44 pm
SXM
-
ORD
11h 02m
1 stop
$437Multiple 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
$446JetBlue
Wed, Aug 26 - Mon, Aug 31
Southwest Logo
5:20 pm - 2:05 pm
MDW
-
SXM
19h 45m
2 stops
Southwest Logo
3:05 pm - 10:40 pm
SXM
-
MDW
8h 35m
1 stop
$447Southwest
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
$451JetBlue
Wed, Sep 9 - Fri, Sep 25
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
$453JetBlue
Tue, Jul 14 - Tue, Jul 21
Southwest Logo
5:10 am - 2:00 pm
MDW
-
SXM
7h 50m
1 stop
Southwest Logo
3:00 pm - 10:05 pm
SXM
-
MDW
8h 05m
1 stop
$510Southwest
Tue, Jul 14 - Tue, Jul 21
Southwest Logo
5:10 am - 2:00 pm
MDW
-
SXM
7h 50m
1 stop
Southwest Logo
3:00 pm - 8:40 am
SXM
-
MDW
18h 40m
2 stops
$515Southwest
Booking Insights

KAYAK's insights & trends for Chicago to St. Maarten flights

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

What is the cheapest Chicago to St. Maarten flight route?

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

The cheapest ticket to St. Maarten from Chicago found in the last 5 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 5 days was $482.

What is the cheapest time of day to fly to St. Maarten?

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

The cheapest time of day to fly to St. Maarten is generally in the morning, when round-trip flights cost $784 on average. The most expensive time of day to fly to St. Maarten is generally in the morning, which is peak travel time and where the average cost of a ticket is $784.

Can I save money by flying with a layover from Chicago to St. Maarten?

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 2 stops layover the cheapest option at $674 on average.

What is the cheapest month to fly from Chicago to St. Maarten?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to St. Maarten, 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 St. Maarten 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 $376 respectively.

How far in advance should I book a flight from Chicago to St. Maarten?

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 St. Maarten, 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 St. Maarten, 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$146
Best time to beat the crowds but there is an average 1% increase 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 St. Maarten flights

  • How does KAYAK find such low prices on flights from Chicago to St. Maarten?

    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 St. Maarten.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to St. Maarten?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to St. Maarten 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 St. Maarten?

    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 St. Maarten 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 St. Maarten?

    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 St. Maarten 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 St. Maarten

 
Need help choosing which airline to fly with from Chicago to St. Maarten? 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
7.8Entertainment
7.8Comfort
7.2Food
8.1Boarding
8.5Crew
Airline reviews

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

2.0 MediocreAnonymous, Jun 2026
RDU - LGA
Read more Delta reviews

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

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.

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.

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.

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

Everything you need to know for your flight from Chicago to St. Maarten

Cabin class types available on flights to St. Maarten

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