$139 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 10/31. 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

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Cheap Flights from O'Hare Intl to St. Maarten

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Simpson Bay
Simpson Bay1 stop$312
Simpson Bay
Simpson Bay1 stop$312

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, Sep 6 - Sat, Sep 13
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
$312Spirit Airlines
Find Deal
Sat, Aug 30 - Sat, Sep 6
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
$317Spirit Airlines
Find Deal
Sat, Aug 16 - Sat, Aug 23
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
3:05 pm - 11:59 pmSXM-ORD
9h 54m1 stop
$335Spirit Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
3:05 pm - 11:45 pmSXM-ORD
9h 40m1 stop
$353Spirit Airlines
Find Deal
Mon, Sep 8 - Mon, Sep 22
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
$354Spirit Airlines
Find Deal
Sat, Oct 25 - Sat, Nov 1
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
3:05 pm - 12:31 amSXM-ORD
10h 26m1 stop
$363Spirit Airlines
Find Deal
Fri, Sep 5 - Sat, Sep 13
Spirit Airlines Logo
5:05 am - 2:00 pmORD-SXM
7h 55m1 stop
Spirit Airlines Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
$377Spirit Airlines
Find Deal
Sat, Jan 24 - Sat, Jan 31
Spirit Airlines Logo
5:05 am - 3:10 pmORD-SXM
8h 05m1 stop
Spirit Airlines Logo
4:28 pm - 11:42 pmSXM-ORD
9h 14m1 stop
$399Spirit Airlines
Find Deal
Mon, Aug 18 - Wed, Aug 27
 Logo
6:56 am - 5:21 pmORD-SXM
9h 25m2 stops
 Logo
3:05 pm - 11:59 pmSXM-ORD
9h 54m1 stop
Tue, Sep 16 - Fri, Sep 26
 Logo
10:27 am - 8:12 amORD-SXM
20h 45m2 stops
 Logo
3:05 pm - 10:48 pmSXM-ORD
8h 43m1 stop
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.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport 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 1 stop layover the cheapest option at $2,524 on average.

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 May, when tickets cost $672 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $934 and $833 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, Tuesday 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 Sunday 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 2 weeks before departure, which saves you about 18% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.


Good to know

Low seasonAugust
Cheapest flight$139
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 9% 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 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.

  • 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 82% 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 $892.

Reviews of the top 4 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.
8.0
DeltaOverall score based on 7981 reviews
8.2Boarding
7.3Food
7.9Comfort
7.9Entertainment
8.5Crew
Airline reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

2.0 MediocreGim, Jul 2025BGM - DTW
Read more Delta reviews

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

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

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.

The flight was on time, boarding was efficient, staff was nice. Seats seem to have been upgraded on this model and were clean and tidy. I did not purchase in flight snacks.

check in at security was a hassle being scanned. Spirit employees were helpful and professional.

First time on Spirit. Definitely a streamline flight but I would fly Spirit again.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

Had a issue with catching flight due to airline, was unable to board flight

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

Not great. Seats uncomfortable. Crew a little rude. Amenities like wifi and drinks way too expensive.

Late departure by 1:45min. No explanation why. During boarding inconsistent policing of their baggage rules. Before takeoff and lamdimg strange obsession with window shade and armrest positions. Don't know why they care. 15 min tarmac delay on arrival, they blamed airport congestion but we were the o lh flight waiting, it was clear it was due to poor staff planning (only one ground crew to receive airplanes and multiple arrivals) Got there but was rrally lame the whole trip.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

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

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