$129 Find Cheap Flights from Chicago to St. Maarten

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 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.
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Best St. Maarten Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Simpson Bay
Simpson Bay1 stop$337

Cheap Flight Deals from Chicago to St. Maarten (CHI-SX0)

 
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.

Recent round-trip flight deals from Chicago to St. Maarten

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to St. Maarten.
Discover the best prices for you by selecting your travel dates on KAYAK.
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Spirit Airlines Logo
5:36 am - 2:00 pmORD-SXM
7h 24m1 stop
Spirit Airlines Logo
3:05 pm - 12:58 amSXM-ORD
10h 53m1 stop
$337Spirit Airlines
Find Deal
Sat, Apr 26 - Sat, May 3
Spirit Airlines Logo
7:33 pm - 2:00 pmORD-SXM
17h 27m1 stop
Spirit Airlines Logo
3:05 pm - 12:58 amSXM-ORD
10h 53m1 stop
$347Spirit Airlines
Find Deal
Sun, Apr 27 - Sat, May 3
Frontier Logo
3:16 pm - 5:01 pmORD-SXM
48h 45m2 stops
Frontier Logo
12:34 pm - 8:22 amSXM-ORD
20h 48m1 stop
$398Frontier
Find Deal
Sat, May 17 - Sat, May 24
 Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
 Logo
12:34 pm - 8:22 amSXM-ORD
20h 48m1 stop
Sat, May 17 - Sat, May 24
 Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
 Logo
12:34 pm - 8:22 amSXM-ORD
20h 48m1 stop
Sat, May 17 - Sat, May 24
Frontier Logo
3:16 pm - 5:01 pmORD-SXM
48h 45m2 stops
Frontier Logo
12:34 pm - 12:04 amSXM-ORD
12h 30m1 stop
$424Frontier
Find Deal
Sat, May 17 - Sat, May 24
Delta Logo
5:30 am - 1:54 pmORD-SXM
7h 24m1 stop
Delta Logo
3:19 pm - 11:58 pmSXM-ORD
9h 39m1 stop
$622Delta
Find Deal
Tue, May 13 - Fri, May 23
American Airlines Logo
8:27 pm - 1:00 pmORD-SXM
15h 33m2 stops
American Airlines Logo
2:24 pm - 12:11 amSXM-ORD
10h 47m2 stops
$627American Airlines
Find Deal
Sat, May 3 - Wed, May 7
Delta Logo
5:30 am - 1:54 pmORD-SXM
7h 24m1 stop
Delta Logo
3:19 pm - 11:58 pmSXM-ORD
9h 39m1 stop
$647Delta
Find Deal
Thu, May 15 - Fri, May 23
American Airlines Logo
8:27 pm - 1:00 pmORD-SXM
15h 33m2 stops
American Airlines Logo
4:40 pm - 9:00 amSXM-ORD
17h 20m1 stop
$652American Airlines
Find Deal
Sat, May 3 - Sat, May 10

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to St. Maarten.
The cheapest ticket to St. Maarten from Chicago found in the last 72 hours was to Simpson Bay, at $757 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 $757.

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 afternoon, when round-trip flights cost $417 on average. Morning departures are around 86% more expensive than evening flights, 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 $913.

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.
No, with an average price for the route of $1,304, prices are generally cheapest when you fly direct.

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 $609 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $828 and $819 respectively.

What’s the cheapest day of the week to fly from Chicago to St. Maarten?

The average price of all round-trip flights from Chicago to St. Maarten clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to St. Maarten on a Monday and more expensive on a Saturday. On your return trip to Chicago, you should consider flying back on a Monday, and avoid Sundays for better deals.

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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low season

October

High season

March

Cheapest flight

$129
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 12% increase in price.
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.

See more FAQs

Top 4 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.
8.0
DeltaOverall score based on 7897 reviews
7.9Entertainment
8.2Boarding
7.3Food
8.5Crew
7.9Comfort
Airline reviews

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

10.0 ExcellentSunderesh, Mar 2025AUS - BOS
Read more Delta reviews

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

After a 5 hour delay waiting at the gate (3 delays adding up) with no clear reason provided, we finally boarded flew 3/4 of the way to Toronto then were turned back to New York. As we neared New York, the pilot declared that it was his fault, something to do with timing and him not being allowed into the country???? How could the airline let his happen? They had hours to prepare and make sure they had a crew available for the flight! We ended up in Toronto a day late with no sleep.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Friendly flight attendants, smooth 8-9 hours flight. Economy seats are small and uncomfortable as usual.

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Bathrooms dirty sinks clogged. No one seemed to clean them. Plane very old

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

Fight was delayed an hour due to operational issues ,then further delayed due to ground control for a total of about 1.30 hours. Salad was completely frozen and flatware was so cold you could barely handle it. Crew was friendly and professional and the flight was smooth. The aircraft was clean and well-serviced.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Last minute 2-3 hr delay in flight schedule; no explanation Unexpected extra $52 charge What's the benefit of choosing a cheap airline if you trick people last minute and force them to pay extra last minute? Did not appreciate being cornered.

I book a filght for me and my daughter from Miami home to Las Vegas and getting her checked in was awful the lady at the baggage check in was horrible!!! She was the rudest person I have ever encountered in my entire life!!!! My daughter dose not speak Spanish and so I was trying to translate for her but the woman would not let me so my daughter was 100 💯 confused because she could not understand what was going on or being said at all horrible absolutely horrible and rude extremely stressful worst experience ever!!!!!!! And then we were actually told by other air port staff not to complain because if we did sprint would make sure we miss our flight ✈️ that they do it all the time 😧

Terrible! They kept postponing and finally canceled our flight. They canceled so late. We had no other options but to drive to a different city and try to find a new flight to get onto our cruise. We still aren’t there yet and might not make it.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

The flight was on time. The seats are very narrow.

My only complaint is that the standing recline. I wasn’t aware of that when I booked the ticket.

Unclear pricing; ended up being charged an extra $52 just to get onboard

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

No leg room AT all extremely uncomfortable flight water even cost 5 dollars

Seats are poor. They do not lean back. They do not even have pockets on the back, making it impossible to store a phone or a coke bottle. If you opt for basic economy cheap seats, they stick you always in the middle or window seat, even though there are unoccupied seats on the aisle. And then there is the nickel and diming. No carry-ons. And checking your carry-on is $70. At the end there is no price advantage but there is plenty of aggravation.

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.

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