$171 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 9/25. 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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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

Sun, Oct 25 - Sat, Oct 31
Air Canada Logo
10:15 am - 2:45 pm
ORD
-
SXM
27h 30m
1 stop
Air Canada Logo
2:40 pm - 12:07 pm
SXM
-
ORD
22h 27m
1 stop
$419Air Canada
Sun, Oct 25 - Sat, Oct 31
Air Canada Logo
9:05 pm - 2:45 pm
ORD
-
SXM
16h 40m
1 stop
Air Canada Logo
2:40 pm - 12:07 pm
SXM
-
ORD
22h 27m
1 stop
$420Air Canada
Fri, Nov 27 - Thu, Dec 3
Southwest Logo
5:05 am - 2:20 pm
MDW
-
SXM
7h 15m
1 stop
Southwest Logo
3:20 pm - 5:40 am
SXM
-
MDW
16h 20m
2 stops
$448Southwest
Sat, Sep 5 - Sat, Sep 12
Multiple Airlines Logo
6:00 am - 4:19 pm
ORD
-
SXM
9h 19m
1 stop
Multiple Airlines Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
$463Multiple Airlines
Sat, Aug 22 - Sat, Aug 29
JetBlue Logo
6:00 am - 4:19 pm
ORD
-
SXM
9h 19m
1 stop
JetBlue Logo
11:20 am - 9:58 pm
SXM
-
ORD
11h 38m
1 stop
$506JetBlue
Sat, Sep 5 - Thu, Sep 10
JetBlue Logo
6:00 am - 4:19 pm
ORD
-
SXM
9h 19m
1 stop
JetBlue Logo
3:05 pm - 11:08 pm
SXM
-
ORD
9h 03m
1 stop
$510JetBlue
Tue, Sep 8 - Tue, Sep 15
American Airlines Logo
6:59 am - 3:39 pm
ORD
-
SXM
7h 40m
1 stop
American Airlines Logo
2:23 pm - 12:33 am
SXM
-
ORD
11h 10m
1 stop
$656American Airlines
Tue, Sep 8 - Tue, Sep 15
American Airlines Logo
5:05 am - 3:39 pm
ORD
-
SXM
9h 34m
2 stops
American Airlines Logo
2:23 pm - 12:33 am
SXM
-
ORD
11h 10m
1 stop
$657American Airlines
Sat, Dec 12 - Sun, Dec 20
United Airlines Logo
8:45 am - 3:57 pm
ORD
-
SXM
5h 12mnonstop
United Airlines Logo
2:10 pm - 6:11 pm
SXM
-
ORD
6h 01mnonstop
$660United Airlines
Sat, Nov 14 - Sat, Nov 21
United Airlines Logo
8:40 am - 3:57 pm
ORD
-
SXM
5h 17mnonstop
United Airlines Logo
5:00 pm - 11:37 pm
SXM
-
ORD
8h 37m
1 stop
$661United Airlines
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 $647 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 $647.

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 $782 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 $782.

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 September, when tickets cost $418 (return) on average. On the other hand, the most expensive months are June and April, when the average cost of round-trip tickets is $785 and $779 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 39% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low season

August

Cheapest flight

$171
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 14% 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.
7.8
DeltaOverall score based on 8482 reviews
7.8Comfort
8.1Boarding
7.8Entertainment
7.2Food
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 SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

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.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

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.

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.