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 is the cheapest airline that flies from Chicago O'Hare Intl to St. Maarten?

Spirit Airlines and Air Canada are the most popular carriers operating from Chicago O'Hare Intl to St. Maarten

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 20% of their flights experiencing any sort of delay.

What airlines fly to St. Maarten?

American Airlines, United Airlines and Spirit Airlines 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 52% of people opting to fly with this airline when traveling to St. Maarten. Keep in mind that there are 6 different airlines that fly to St. Maarten on a routine basis, so you have a few additional options to choose from.

How many flights depart from Chicago O'Hare Intl Airport to St. Maarten on average per week?

2 flights are operational weekly from Chicago O'Hare Intl Airport to St. Maarten as of March 2026. The most popular departure day for this route is Sat, with 50% of flights per week taking off on this day.

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.

How often are flights from Chicago to St. Maarten delayed?

Historically, on average around 26% 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 94 minutes.

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 6 as of March 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.

$94 Cheap Flights from Chicago O'Hare Intl Airport to St. Maarten in 2026

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Find the cheapest flights from Chicago O'Hare Intl Airport to St. Maarten

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:05 am - 1:30 pm

ORD

SXM

7h 25m

1 stop

2:42 pm - 12:24 am

SXM

ORD

10h 42m

1 stop

$308Spirit Airlines

Sat, Apr 4 - Thu, Apr 16

5:05 am - 1:30 pm

ORD

SXM

7h 25m

1 stop

2:42 pm - 12:24 am

SXM

ORD

10h 42m

1 stop

$320Spirit Airlines

Sat, Apr 4 - Thu, Apr 16

7:15 pm - 1:37 pm

ORD

SXM

17h 22m

1 stop

2:42 pm - 12:24 am

SXM

ORD

10h 42m

1 stop

$330Spirit Airlines

Sat, Apr 25 - Sat, May 9

7:15 pm - 1:37 pm

ORD

SXM

17h 22m

1 stop

2:42 pm - 12:24 am

SXM

ORD

10h 42m

1 stop

$333Spirit Airlines

Wed, May 6 - Sat, May 9

5:05 am - 1:30 pm

ORD

SXM

7h 25m

1 stop

2:35 pm - 9:36 am

SXM

ORD

20h 01m

1 stop

$334Spirit Airlines

Tue, Apr 7 - Tue, Apr 14

5:05 am - 1:30 pm

ORD

SXM

7h 25m

1 stop

2:35 pm - 9:17 pm

SXM

ORD

31h 42m

1 stop

$335Multiple Airlines

Tue, Apr 7 - Tue, Apr 14

5:05 am - 1:37 pm

ORD

SXM

7h 32m

1 stop

2:42 pm - 12:24 am

SXM

ORD

10h 42m

1 stop

$339Spirit Airlines

Sat, Apr 18 - Sat, Apr 25

5:05 am - 1:30 pm

ORD

SXM

7h 25m

1 stop

2:42 pm - 12:24 am

SXM

ORD

10h 42m

1 stop

$340Spirit Airlines

Sat, Apr 11 - Thu, Apr 16

5:05 am - 1:30 pm

ORD

SXM

7h 25m

1 stop

2:35 pm - 8:50 am

SXM

ORD

19h 15m

2 stops

$342Spirit Airlines

Thu, Apr 2 - Tue, Apr 7

5:05 am - 1:30 pm

ORD

SXM

7h 25m

1 stop

2:35 pm - 11:17 pm

SXM

ORD

9h 42m

1 stop

$344Spirit Airlines

Thu, Apr 2 - Wed, Apr 8

Spirit Airlines flights from Chicago O'Hare Intl Airport to St. Maarten

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to St. Maarten flight tickets

Spirit Airlines

Apr 4

ORD5:05 amChicago O'Hare Intl

7h 25m

1 stop

SXM1:30 pmSimpson Bay Princess Juliana

Apr 16

SXM2:42 pmSimpson Bay Princess Juliana

10h 42m

1 stop

ORD12:24 amChicago O'Hare Intl

$308

Spirit Airlines

Apr 4

ORD5:05 amChicago O'Hare Intl

7h 25m

1 stop

SXM1:30 pmSimpson Bay Princess Juliana

Apr 16

SXM2:42 pmSimpson Bay Princess Juliana

10h 42m

1 stop

ORD12:24 amChicago O'Hare Intl

$320

Spirit Airlines

Apr 25

ORD7:15 pmChicago O'Hare Intl

17h 22m

1 stop

SXM1:37 pmSimpson Bay Princess Juliana

May 9

SXM2:42 pmSimpson Bay Princess Juliana

10h 42m

1 stop

ORD12:24 amChicago O'Hare Intl

$330

Air Canada flights from Chicago O'Hare Intl Airport to St. Maarten

Our best Air Canada deals on Chicago O'Hare Intl Airport to St. Maarten flight tickets

Air Canada

Mar 30

ORD12:50 pmChicago O'Hare Intl

23h 45m

1 stop

SXM1:35 pmSimpson Bay Princess Juliana

Apr 3

SXM4:00 pmSimpson Bay Princess Juliana

18h 10m

1 stop

ORD9:10 amChicago O'Hare Intl

$387

Air Canada

Mar 25

ORD7:25 amChicago O'Hare Intl

29h 15m

2 stops

SXM1:40 pmSimpson Bay Princess Juliana

Apr 3

SXM4:00 pmSimpson Bay Princess Juliana

27h 58m

2 stops

ORD6:58 pmChicago O'Hare Intl

$388

Air Canada

Mar 30

ORD12:50 pmChicago O'Hare Intl

23h 45m

1 stop

SXM1:35 pmSimpson Bay Princess Juliana

Apr 3

SXM4:00 pmSimpson Bay Princess Juliana

19h 53m

2 stops

ORD10:53 amChicago O'Hare Intl

$391

momondo Fare Finder

Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to St. Maarten that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/4

5:05 am-1:30 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Thu 4/16

2:42 pm-12:24 am

1 stop10h 42m

$308

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/4

5:05 am-1:30 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Thu 4/16

2:42 pm-12:24 am

1 stop10h 42m

$320

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/25

7:15 pm-1:37 pm

1 stop17h 22m

Simpson Bay Princess Juliana

Sat 5/9

2:42 pm-12:24 am

1 stop10h 42m

$330

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 5/6

7:15 pm-1:37 pm

1 stop17h 22m

Simpson Bay Princess Juliana

Sat 5/9

2:42 pm-12:24 am

1 stop10h 42m

$333

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 4/7

5:05 am-1:30 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Tue 4/14

2:35 pm-9:36 am

1 stop20h 01m

$334

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 4/7

5:05 am-1:30 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Tue 4/14

2:35 pm-9:17 pm

1 stop31h 42m

$335

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/18

5:05 am-1:37 pm

1 stop7h 32m

Simpson Bay Princess Juliana

Sat 4/25

2:42 pm-12:24 am

1 stop10h 42m

$339

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/11

5:05 am-1:30 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Thu 4/16

2:42 pm-12:24 am

1 stop10h 42m

$340

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 4/2

5:05 am-1:30 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Tue 4/7

2:35 pm-8:50 am

2 stops19h 15m

$342

Quickest round-trip

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 4/2

5:05 am-1:30 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Wed 4/8

2:35 pm-11:17 pm

1 stop9h 42m

$344

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

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Other information

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 $489, 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 $578.

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 $625. 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 $796.

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 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 $649 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 $474 on momondo.

What cabin class options are available on Chicago O'Hare Intl to St. Maarten flights?

There are 2 cabin classes available to choose from on Chicago O'Hare Intl 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 69% on your flight if you consider stops on a Chicago O'Hare Intl Airport to St. Maarten flight.

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

Best Price Found	$304
Fastest flight time	5h 12m
Direct flights	Mon and Sun
Airports in St. Maarten	2 airports

The best one-way flight to St. Maarten from Chicago O'Hare Intl Airport in the past 72 hours is $304. The best round-trip flight deal from Chicago O'Hare Intl Airport to St. Maarten found on momondo in the last 72 hours is $891.

The fastest flight from Chicago O'Hare Intl Airport to St. Maarten takes 5h 12m

Direct flights go from Chicago O'Hare Intl Airport to St. Maarten on Monday and Sunday. There are no airlines offering direct flights.

There are 2 airports in St. Maarten. From Chicago O'Hare Intl Airport there are direct flights to Simpson Bay Princess Juliana (SXM).

Search flight deals

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 6 as of March 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 54.26% of all bookings. The subsequent popular models are Airbus A319 at 30.85%, Boeing 737-700 at 6.38%, and Airbus A321-100/200 at 3.19%.

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
Spirit Airlines	PriceFrom $231	Free Cancellation	Rating 6.3 8,509 reviews	Search Spirit Airlines flights
Delta	PriceFrom $290	Free Cancellation	Rating 7.9 8,276 reviews	Search Delta flights
United Airlines	PriceFrom $389	Free Cancellation	Rating 7.4 9,409 reviews	Search United Airlines flights
Air Canada	PriceFrom $487	Free Cancellation	Rating 7.1 10,800 reviews	Search Air Canada flights
American Airlines	PriceFrom $501	Free Cancellation	Rating 7.1 11,409 reviews	Search American Airlines flights
JetBlue	PriceFrom $568	Free Cancellation	Rating 7.2 2,900 reviews	Search JetBlue flights

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.

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How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to St. Maarten

What is the cheapest month to fly to St. Maarten?

What is the cheapest day to depart on your flight to St. Maarten?

What is the cheapest Chicago O'Hare Intl to St. Maarten flight route?

How far in advance should I book a flight to St. Maarten?

What cabin class options are available on Chicago O'Hare Intl to St. Maarten flights?

Can stopping save me money on Chicago O'Hare Intl Airport to St. Maarten flights?

What is the cheapest airline that flies from Chicago O'Hare Intl to St. Maarten?

What airlines fly to St. Maarten?

How often are flights from Chicago to St. Maarten delayed?

What is the most punctual flight time for Chicago to St. Maarten flights?

What day of the week experiences the fewest flight delays on this route?

Which airline has the best punctuality record on Chicago to St. Maarten flights?

How many flights depart from Chicago O'Hare Intl Airport to St. Maarten on average per week?

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

Best Price Found

Fastest flight time

Direct flights

Airports in St. Maarten

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

Why use momondo?

An easier way to manage your St. Maarten trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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