$113 Find Cheap Flights from Chicago O'Hare Airport 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 O'Hare Intl to St. Maarten departing on 4/13. 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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Book Cheap O'Hare Intl 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 O'Hare Intl 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 O'Hare Intl to St. Maarten

Sat, May 9 - Sat, May 16
Spirit Airlines Logo
5:05 am - 1:37 pm
ORD
-
SXM
7h 32m
1 stop
Spirit Airlines Logo
2:42 pm - 12:27 am
SXM
-
ORD
10h 45m
1 stop
$339Spirit Airlines
Tue, Apr 7 - Thu, Apr 16
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
$349Spirit Airlines
Tue, Apr 14 - Sat, Apr 25
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
$350Spirit Airlines
Sat, Apr 11 - Tue, Apr 14
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
Spirit Airlines Logo
2:35 pm - 9:36 am
SXM
-
ORD
20h 01m
1 stop
$354Spirit Airlines
Sat, May 2 - Sat, May 9
Spirit Airlines Logo
7:15 pm - 1:37 pm
ORD
-
SXM
17h 22m
1 stop
Spirit Airlines Logo
2:42 pm - 12:27 am
SXM
-
ORD
10h 45m
1 stop
$359Spirit Airlines
Sat, Apr 11 - Sat, Apr 18
Spirit Airlines Logo
6:10 pm - 1:30 pm
ORD
-
SXM
18h 20m
1 stop
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$372Spirit 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
$376Spirit 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
$379Spirit Airlines
Sat, Apr 11 - Sat, Apr 25
Multiple Airlines Logo
3:45 pm - 2:55 pm
ORD
-
SXM
46h 10m
2 stops
Multiple Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$380Multiple Airlines
Sat, Apr 25 - Sat, May 2
Multiple Airlines Logo
6:21 pm - 2:55 pm
ORD
-
SXM
43h 34m
2 stops
Multiple Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
$381Multiple Airlines
Booking Insights

KAYAK's insights & trends for O'Hare Intl to St. Maarten flights

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

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

The average price for all round-trip flights from Chicago O'Hare Intl Airport 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 $786 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 $786.

What is the cheapest month to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to St. Maarten is September, when tickets cost $489 (return) on average. On the other hand, the most expensive months are April and December, when the average cost of round-trip tickets is $794 and $752 respectively.

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

The average price of all round-trip flights from Chicago O'Hare Intl Airport to St. Maarten clicked on KAYAK for each day over the last 12 months.

For Chicago O'Hare Airport to St. Maarten, Sunday is the cheapest day to fly on average and Saturday is the most expensive. Flying from St. Maarten back to Chicago O'Hare Airport, the best deals are generally found on Monday, with Saturday being the most expensive.

How far in advance should I book a flight from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to St. Maarten, 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 seasonAugust
Cheapest flight$114
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 14% 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 O'Hare Airport 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 O'Hare Airport to St. Maarten.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 5 airlines serving from O'Hare Intl to St. Maarten

 
Need help choosing which airline to fly with from O'Hare Intl 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 8286 reviews
8.1Boarding
8.5Crew
7.9Comfort
7.2Food
7.8Entertainment
Airline reviews

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

2.0 MediocreAnonymous, Mar 2026
LAX - BNA
Read more Delta reviews

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

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.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Both flights were significantly delayed. The flight experience itself was great.

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

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?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Absolutely terrible, flight was cancelled and we missed our cruise. Will never fly Spirit again.

Horrendous and unprofessional staff and will never fly spirit again

Like Spirit but bad that you have to pay for water 🙃

My flight was ultimately cancelled but the lack of updates and professionalism from the crew leading up to the cancellation announcement was frustrating for all passengers.

Delay due to personnel issues on Spirit’s end. Original departure time 9:30pm. Took off at 2:15am. Lost an entire night’s sleep bc Spirit couldn’t get a crew together. Very poor.

Sadly the flight was delayed by 4 hours due to the weather snd sir traffic control staffing. Otherwise the crew was amazing and the flight was perfect.

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

I’m still waiting to get on the flight. No one knows what’s happening. The passengers have gotten no updates. We have been up all night and waiting at the airport. This is no way to operate and we should be refunded for this lack of respect for their passengers.

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

Everything you need to know for your flight from O'Hare Intl to St. Maarten

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