$78 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 1/10. 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 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

Sat, Jan 31 - Thu, Feb 5
Spirit Airlines Logo
5:15 am - 2:10 pm
ORD
-
SXM
6h 55m1 stop
Spirit Airlines Logo
3:15 pm - 11:46 pm
SXM
-
ORD
10h 31m1 stop
$231Spirit Airlines
Mon, Feb 9 - Wed, Feb 18
Spirit Airlines Logo
5:15 am - 2:10 pm
ORD
-
SXM
6h 55m1 stop
Spirit Airlines Logo
3:15 pm - 12:18 am
SXM
-
ORD
11h 03m1 stop
$238Spirit Airlines
Sun, Jan 11 - Sat, Jan 17
Spirit Airlines Logo
8:43 pm - 2:10 pm
ORD
-
SXM
15h 27m1 stop
Spirit Airlines Logo
3:15 pm - 11:46 pm
SXM
-
ORD
10h 31m1 stop
$239Spirit Airlines
Thu, Jan 29 - Thu, Feb 5
Spirit Airlines Logo
8:43 pm - 2:10 pm
ORD
-
SXM
15h 27m1 stop
Spirit Airlines Logo
3:15 pm - 11:46 pm
SXM
-
ORD
10h 31m1 stop
$241Spirit Airlines
Sat, Feb 21 - Sat, Feb 28
Multiple Airlines Logo
5:15 am - 2:10 pm
ORD
-
SXM
6h 55m1 stop
Multiple Airlines Logo
3:20 pm - 10:39 pm
SXM
-
ORD
9h 19m1 stop
$246Multiple Airlines
Sat, Feb 21 - Sat, Feb 28
Multiple Airlines Logo
5:15 am - 2:10 pm
ORD
-
SXM
6h 55m1 stop
Multiple Airlines Logo
3:20 pm - 10:39 pm
SXM
-
ORD
9h 19m1 stop
$256Multiple Airlines
Sat, Mar 7 - Sat, Mar 14
Frontier Logo
6:00 am - 3:20 pm
MDW
-
SXM
7h 20m1 stop
Frontier Logo
3:41 pm - 10:04 pm
SXM
-
MDW
7h 23m1 stop
$356Frontier
Sun, Jan 11 - Wed, Jan 21
Delta Logo
9:50 am - 12:30 pm
MDW
-
SXM
24h 40m2 stops
Delta Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
$506Delta
Sat, Apr 4 - Sat, Apr 11
Frontier Logo
6:00 am - 2:40 pm
MDW
-
SXM
7h 40m1 stop
Frontier Logo
3:40 pm - 11:42 pm
SXM
-
MDW
9h 02m1 stop
$517Frontier
Sat, Jan 10 - Thu, Jan 22
Delta Logo
6:45 am - 4:03 pm
MDW
-
SXM
7h 18m1 stop
Delta Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
$531Delta
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 72 hours was to Simpson Bay, at $408 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 $408.

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 August, when tickets cost $585 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $988 and $787 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 Tuesday 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 3 weeks before departure, which saves you about 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$78
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 4% 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.

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

    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 67% 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 $819.

Reviews of the top 5 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 8010 reviews
7.3Food
8.1Boarding
7.9Entertainment
8.5Crew
7.9Comfort
Airline reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

10.0 ExcellentMargaret, Dec 2025
BOS - PIT
Read more Delta reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

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

Our flight got rescheduled 48 hours later, the airline didn’t pay a penny for our expenses.

We had to sit and wait for almost an hour after landing and taxiing to the gate. The jet bridge was broken so we just waited and waited and waited and it was inconvenient, hot, and unnecessary.

Flight was in time, very smooth ride and surprisingly lots of legroom in the cabin so I certainly will fly with spirit again

The seats are the most uncomfortable seats I’ve ever sat in. Don’t believe I’ll ever fly spirit again!!

Flight was canceled and instead of rescheduling at the gate we had to go out to the ticket counter. Unruly kids kicking the back of my rows chair with staff to inattentive to say something.

Customer feedback I sent to Spirited today: “I will never fly Spirit Airlines again and will work hard to convince my friends and family to boycott/avoid Spirit Airlines at all costs. I booked three seats for me and my 8 and 10 year old children on NK 1222 from Orlando to Kansas City for 12/7/25 leaving Orlando at 10:37AM. This itinerary was abandoned by Spirit and we were rebooked onto Spirit flight NK 213 leaving at 9:06PM without any notice. Then the nightmare really began. Flight 213 was delayed a total of 12 times, finally leaving at 6:35AM the following day. The gate was changed 5 times and our electronic boarding passes were invalidated at midnight. The worst part was that the 12 separate delays were incremental making it impossible to plan for accommodations for my family. My kids missed a day of school and barely slept under the harsh lights with lots of noise on the filthy airport floor. The customer service agent at Spirit Airlines told us we would be emailed a voucher for a hotel which never happened. I asked about it multiple times and it never arrived in my email inbox. This whole unfortunate situation could’ve been avoided if spirit had taken a realistic approach and delayed the flight from 9 PM until 6 AM from the beginning. My son gleefully deleted the Spirit app from my phone once we landed and we will never fly with Spirit again.”

Honestly horrible. The plane on the way back was delayed 6 times with no explanation on why. When I asked for a refund or some money back because I had to miss a day of work because of the desk, they told me no. Because of how poorly it was handled I will most likely never take spirit again

I love a flight without turbulence and you guys deliver It’d be nice to have comfier seats and maybe some inflight entertainment and snacks but that’s for Delta

30 minute delay, Also there was a medical emergency on the flight. The flight crew was on top of the situation and assisted the medical professionals that happened to be on the flight.

This was my first time on a budget airline and I couldn't even sit down all the way because my knees would embed in the seat in front of me. I'm only 6' tall with a 32" inseam. There's no upside other than y'all are cheap. I'm glad it was only a 2 hour flight. Lesson learned! I get why everybody talks down on budget airlines. The staff was outstanding, the flight went as well as possible, great pilot, great boarding, smooth sailing. Zero chance I'll be back though.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

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.