Cheap flights from Chicago O'Hare Intl Airport to St. Maarten from $143
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to St. Maarten departing on 12/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Wed 12/2
1:55 pm-2:45 pm
1 stop22h 50m
Simpson Bay Princess Juliana
Sun 12/6
4:45 pm-1:13 pm
1 stop22h 28m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Wed 12/2
1:55 pm-2:45 pm
1 stop22h 50m
Simpson Bay Princess Juliana
Sun 12/6
4:45 pm-1:13 pm
1 stop22h 28m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Sun 1/24
7:00 pm-12:15 pm
1 stop15h 15m
Simpson Bay Princess Juliana
Tue 2/2
4:05 pm-7:39 am
1 stop17h 34m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Mon 1/25
5:30 am-2:40 pm
1 stop7h 10m
Simpson Bay Princess Juliana
Thu 1/28
1:40 pm-11:50 pm
1 stop12h 10m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Sun 11/8
5:19 am-2:30 pm
1 stop7h 11m
Simpson Bay Princess Juliana
Fri 11/13
5:33 pm-8:00 am
1 stop16h 27m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Tue 12/22
8:40 am-3:57 pm
Nonstop5h 17m
Simpson Bay Princess Juliana
Wed 12/30
2:10 pm-6:11 pm
Nonstop6h 01m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Tue 12/22
8:40 am-3:57 pm
Nonstop5h 17m
Simpson Bay Princess Juliana
Wed 12/30
2:10 pm-6:11 pm
Nonstop6h 01m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Sun 11/8
8:57 pm-1:26 pm
2 stops14h 29m
Simpson Bay Princess Juliana
Wed 11/11
5:33 pm-7:27 am
2 stops15h 54m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Mon 12/28
7:55 pm-12:21 pm
1 stop14h 26m
Simpson Bay Princess Juliana
Wed 1/6
2:22 pm-11:42 pm
1 stop11h 20m
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Thu 12/31
7:55 pm-12:21 pm
1 stop14h 26m
Simpson Bay Princess Juliana
Wed 1/6
2:22 pm-11:42 pm
1 stop11h 20m
See travel insights to St. Maarten from
How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to St. Maarten
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to St. Maarten?
The cheapest month to fly to St. Maarten from Chicago O'Hare Intl Airport is in September. Flight prices, which tend to average around $389, are often lower during this time because this is during the off-season. If you’re not able to fly to St. Maarten in September, then February is your next best option. Flight prices from Chicago O'Hare Intl Airport to St. Maarten during February average around $565.
What is the cheapest day to depart on your flight to St. Maarten?
According to our data, Sunday is the cheapest day to fly to St. Maarten from Chicago O'Hare Intl Airport. The lowest ticket price found for a Sunday departure recently was $553. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. The most expensive day to fly to St. Maarten is Saturday, with ticket prices averaging around $780.
What is the cheapest Chicago O'Hare Intl to St. Maarten flight route?
Fly from Chicago O'Hare Intl to Simpson Bay Princess Juliana for the best Chicago O'Hare Intl - St. Maarten flight prices
How far in advance should I book a flight from Chicago O'Hare Intl Airport to St. Maarten?
You are more likely to see cheaper flights to St. Maarten from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to St. Maarten for around $689 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to St. Maarten from Chicago O'Hare Intl Airport for as low as $532 on momondo.
What cabin class options are available on Chicago O'Hare Intl Airport to St. Maarten flights?
There are 4 cabin classes available to choose from on Chicago O'Hare Intl Airport to St. Maarten flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Chicago O'Hare Intl Airport to St. Maarten flights?
You could potentially save up to 33% on your flight if you consider stops on a Chicago O'Hare Intl Airport to St. Maarten flight.
What is the cheapest airline that flies from Chicago O'Hare Intl to St. Maarten?
Air Canada is the most popular carrier operating from Chicago O'Hare Intl to St. Maarten
What airlines fly to St. Maarten?
American Airlines, United Airlines and JetBlue are the top three most popular airlines that fly to St. Maarten from Chicago O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 55% of people opting to fly with this airline when traveling to St. Maarten. Keep in mind that there are 4 different airlines that fly to St. Maarten on a routine basis, so you have a few additional options to choose from.
How often are flights from Chicago to St. Maarten delayed?
Historically, on average around 25% of flights between Chicago and St. Maarten have experienced a delay on any given week. The average delay length over the past 12 months has been 105 minutes.
What is the most punctual flight time for Chicago to St. Maarten flights?
Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.
What day of the week experiences the fewest flight delays on this route?
Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.
Which airline has the best punctuality record on Chicago to St. Maarten flights?
According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 21% of their flights experiencing any sort of delay.
Cheap Chicago O'Hare Intl Airport to St. Maarten flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to St. Maarten
Frequently asked questions about flying from Chicago O'Hare Intl Airport to St. Maarten
When did momondo last update prices for flights from Chicago O'Hare Intl Airport to St. Maarten?
Prices for flights from Chicago O'Hare Intl Airport to St. Maarten are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to St. Maarten?
The number of operators available for flights from Chicago O'Hare Intl Airport to St. Maarten is 4 as of October 2026.
How old do you have to be to fly from Chicago O'Hare Intl Airport to St. Maarten?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to St. Maarten.
What documentation or ID do you need to fly to St. Maarten?
The travel and health documents required for your trip to St. Maarten can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at St. Maarten. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago O'Hare Intl Airport to St. Maarten?
momondo data reveals that the most frequently booked plane model on the route from Chicago O'Hare Intl Airport to St. Maarten is Boeing 737 MAX 8, representing 63.22% of all bookings. The subsequent popular models are Airbus A319 at 22.99%, Boeing 737-700 at 6.90%, and Airbus A318/A319/A320/A321 at 2.30%.
Best airlines flying from Chicago O'Hare Intl Airport to St. Maarten
Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to St. Maarten with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $240 | Free Cancellation | Rating 7.8 8,628 reviews | |||
| PriceFrom $389 | Free Cancellation | Rating 7.1 3,040 reviews | |||
| PriceFrom $410 | Free Cancellation | Rating 7.4 10,281 reviews | |||
| PriceFrom $501 | Free Cancellation | Rating 7.0 12,125 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to St. Maarten?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to St. Maarten. momondo saves you time and could save you money on your trip.
Can I find flights from Chicago to St. Maarten with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Chicago to St. Maarten flights to just show those with flexible booking policies.
How can momondo help me find flights from Chicago to St. Maarten?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to St. Maarten.
I’m not ready to book a flight from Chicago to St. Maarten right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Chicago to St. Maarten flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.