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

JetBlue and Delta are the most popular carriers operating from Chicago O'Hare Intl to St. Maarten

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.

What airlines fly to St. Maarten?

American Airlines, United Airlines and Delta 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 61% of people opting to fly with this airline when traveling to St. Maarten. Keep in mind that there are 5 different airlines that fly to St. Maarten on a routine basis, so you have a few additional options to choose from.

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.

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.

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 5 as of June 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.

$163 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.

2:35 pm - 12:38 pm

ORD

SXM

21h 03m

1 stop

1:45 pm - 11:44 pm

SXM

ORD

10h 59m

1 stop

$420JetBlue

Mon, Sep 14 - Sun, Sep 20

5:13 pm - 11:30 am

ORD

SXM

17h 17m

1 stop

1:42 pm - 11:44 pm

SXM

ORD

11h 02m

1 stop

$432Multiple Airlines

Fri, Jul 10 - Thu, Jul 16

10:16 am - 11:30 am

ORD

SXM

24h 14m

1 stop

1:42 pm - 11:44 pm

SXM

ORD

11h 02m

1 stop

$438Multiple Airlines

Fri, Jul 10 - Thu, Jul 16

2:35 pm - 12:38 pm

ORD

SXM

21h 03m

1 stop

1:45 pm - 11:44 pm

SXM

ORD

10h 59m

1 stop

$440JetBlue

Tue, Sep 8 - Thu, Sep 24

6:27 pm - 10:02 am

ORD

SXM

14h 35m

1 stop

1:42 pm - 11:44 pm

SXM

ORD

11h 02m

1 stop

$446JetBlue

Tue, Sep 1 - Wed, Sep 2

5:27 pm - 10:07 am

ORD

SXM

15h 40m

1 stop

1:42 pm - 11:44 pm

SXM

ORD

11h 02m

1 stop

$450JetBlue

Fri, Jul 10 - Thu, Jul 16

8:40 pm - 5:00 pm

ORD

SXM

19h 20m

1 stop

6:00 pm - 9:00 am

SXM

ORD

16h 00m

1 stop

$451Air Canada

Fri, Jul 31 - Sat, Aug 8

2:35 pm - 12:38 pm

ORD

SXM

21h 03m

1 stop

1:45 pm - 11:44 pm

SXM

ORD

10h 59m

1 stop

$456JetBlue

Wed, Sep 9 - Sun, Sep 13

6:00 am - 4:22 pm

ORD

SXM

9h 22m

1 stop

1:42 pm - 11:44 pm

SXM

ORD

11h 02m

1 stop

$457JetBlue

Sat, Jul 25 - Thu, Jul 30

7:15 am - 2:10 pm

ORD

SXM

28h 55m

1 stop

2:30 pm - 11:44 pm

SXM

ORD

11h 14m

1 stop

$465Multiple Airlines

Wed, Nov 11 - Wed, Nov 18

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

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

JetBlue

Sep 14

ORD2:35 pmChicago O'Hare Intl

21h 03m

1 stop

SXM12:38 pmSimpson Bay Princess Juliana

Sep 20

SXM1:45 pmSimpson Bay Princess Juliana

10h 59m

1 stop

ORD11:44 pmChicago O'Hare Intl

$420

JetBlue

Sep 8

ORD2:35 pmChicago O'Hare Intl

21h 03m

1 stop

SXM12:38 pmSimpson Bay Princess Juliana

Sep 24

SXM1:45 pmSimpson Bay Princess Juliana

10h 59m

1 stop

ORD11:44 pmChicago O'Hare Intl

$440

JetBlue

Sep 1

ORD6:27 pmChicago O'Hare Intl

14h 35m

1 stop

SXM10:02 amSimpson Bay Princess Juliana

Sep 2

SXM1:42 pmSimpson Bay Princess Juliana

11h 02m

1 stop

ORD11:44 pmChicago O'Hare Intl

$446

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

Jul 31

ORD8:40 pmChicago O'Hare Intl

19h 20m

1 stop

SXM5:00 pmSimpson Bay Princess Juliana

Aug 8

SXM6:00 pmSimpson Bay Princess Juliana

16h 00m

1 stop

ORD9:00 amChicago O'Hare Intl

$451

Air Canada

Jun 12

ORD8:20 pmChicago O'Hare Intl

19h 40m

1 stop

SXM5:00 pmSimpson Bay Princess Juliana

Jun 27

SXM6:00 pmSimpson Bay Princess Juliana

16h 00m

1 stop

ORD9:00 amChicago O'Hare Intl

$482

Air Canada

Oct 23

ORD5:35 pmChicago O'Hare Intl

22h 25m

1 stop

SXM5:00 pmSimpson Bay Princess Juliana

Oct 26

SXM3:35 pmSimpson Bay Princess Juliana

18h 25m

1 stop

ORD9:00 amChicago O'Hare Intl

$487

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

Mon 9/14

2:35 pm-12:38 pm

1 stop21h 03m

Simpson Bay Princess Juliana

Sun 9/20

1:45 pm-11:44 pm

1 stop10h 59m

$420

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 7/10

5:13 pm-11:30 am

1 stop17h 17m

Simpson Bay Princess Juliana

Thu 7/16

1:42 pm-11:44 pm

1 stop11h 02m

$432

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 7/10

10:16 am-11:30 am

1 stop24h 14m

Simpson Bay Princess Juliana

Thu 7/16

1:42 pm-11:44 pm

1 stop11h 02m

$438

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 9/8

2:35 pm-12:38 pm

1 stop21h 03m

Simpson Bay Princess Juliana

Thu 9/24

1:45 pm-11:44 pm

1 stop10h 59m

$440

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 9/1

6:27 pm-10:02 am

1 stop14h 35m

Simpson Bay Princess Juliana

Wed 9/2

1:42 pm-11:44 pm

1 stop11h 02m

$446

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 7/10

5:27 pm-10:07 am

1 stop15h 40m

Simpson Bay Princess Juliana

Thu 7/16

1:42 pm-11:44 pm

1 stop11h 02m

$450

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 7/31

8:40 pm-5:00 pm

1 stop19h 20m

Simpson Bay Princess Juliana

Sat 8/8

6:00 pm-9:00 am

1 stop16h 00m

$451

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 9/9

2:35 pm-12:38 pm

1 stop21h 03m

Simpson Bay Princess Juliana

Sun 9/13

1:45 pm-11:44 pm

1 stop10h 59m

$456

Quickest round-trip

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 7/25

6:00 am-4:22 pm

1 stop9h 22m

Simpson Bay Princess Juliana

Thu 7/30

1:42 pm-11:44 pm

1 stop11h 02m

$457

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 11/11

7:15 am-2:10 pm

1 stop28h 55m

Simpson Bay Princess Juliana

Wed 11/18

2:30 pm-11:44 pm

1 stop11h 14m

$465

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

Delays

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 February. Flight prices, which tend to average around $74, are often lower during this time because this is during the off-season. If you’re not able to fly to St. Maarten in February, then December is your next best option. Flight prices from Chicago O'Hare Intl Airport to St. Maarten during December average around $240.

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 $617. 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 $795.

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 $654 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 $513 on momondo.

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

There are 2 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?

No. A direct flight is the cheapest option for a flight between Chicago O'Hare Intl Airport to St. Maarten.

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	$722
Fastest flight time	5h 12m
Direct flights	Mon and Sun
Airports in St. Maarten	2 airports

The best flight deal from Chicago O'Hare Intl Airport to St. Maarten found on momondo in the last 72 hours is $722

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

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 5 as of June 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 44.19% of all bookings. The subsequent popular models are Airbus A319 at 25.58%, Boeing 737-700 at 13.95%, and Airbus A318/A319/A320/A321 at 4.65%.

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
Delta	PriceFrom $240	Free Cancellation	Rating 7.8 8,392 reviews	Search Delta flights
United Airlines	PriceFrom $389	Free Cancellation	Rating 7.4 9,777 reviews	Search United Airlines flights
Air Canada	PriceFrom $487	Free Cancellation	Rating 7.1 11,127 reviews	Search Air Canada flights
American Airlines	PriceFrom $500	Free Cancellation	Rating 7.1 11,644 reviews	Search American Airlines flights
JetBlue	PriceFrom $568	Free Cancellation	Rating 7.1 2,982 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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Flights to Simpson Bayfrom $305

Cheap flights from Chicago O'Hare Intl Airport to St. Maarten from $163

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

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

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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.

See travel insights to St. Maarten from

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 from Chicago O'Hare Intl Airport to St. Maarten?

What cabin class options are available on Chicago O'Hare Intl Airport 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?

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

Frequently asked questions about flying from Chicago O'Hare Intl Airport to 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.

Find better results for your trip to St. Maarten

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List of cabin classes available on flights landing in St. Maarten. Availability may vary depending on flight origin and airline.

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