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

JetBlue is the most popular carrier operating from Chicago O'Hare Intl to St. Maarten

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.

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 57% 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.

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 August 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.

$143 Cheap Flights from Chicago O'Hare Intl Airport to St. Maarten in 2026

Discover deals from 900+ travel sites with momondo.

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.

6:00 am - 2:00 pm

ORD

SXM

7h 00m

1 stop

3:05 pm - 11:08 pm

SXM

ORD

9h 03m

1 stop

$372JetBlue

Sat, Sep 26 - Sat, Oct 3

6:00 am - 2:00 pm

ORD

SXM

7h 00m

1 stop

3:05 pm - 11:08 pm

SXM

ORD

9h 03m

1 stop

$372JetBlue

Fri, Sep 18 - Fri, Sep 25

9:55 am - 5:00 pm

ORD

SXM

30h 05m

1 stop

6:00 pm - 4:58 pm

SXM

ORD

23h 58m

1 stop

$409Air Canada

Fri, Sep 11 - Sat, Sep 19

5:35 pm - 5:00 pm

ORD

SXM

22h 25m

1 stop

6:00 pm - 8:12 pm

SXM

ORD

27h 12m

2 stops

$415Air Canada

Fri, Sep 11 - Sat, Sep 19

6:00 am - 2:00 pm

ORD

SXM

7h 00m

1 stop

6:00 pm - 7:44 am

SXM

ORD

14h 44m

2 stops

$416Multiple Airlines

Sat, Sep 26 - Sat, Oct 3

6:21 pm - 5:00 pm

ORD

SXM

21h 39m

2 stops

3:05 pm - 11:08 pm

SXM

ORD

9h 03m

1 stop

$424Multiple Airlines

Fri, Sep 18 - Fri, Sep 25

8:10 am - 2:55 pm

ORD

SXM

4h 45mnonstop

2:30 pm - 6:24 pm

SXM

ORD

5h 54mnonstop

$650American Airlines

Sat, Dec 12 - Sat, Dec 19

7:50 pm - 2:25 pm

ORD

SXM

16h 35m

1 stop

2:30 pm - 6:24 pm

SXM

ORD

5h 54mnonstop

$655American Airlines

Sat, Nov 28 - Sat, Dec 5

6:00 pm - 12:50 pm

ORD

SXM

17h 50m

1 stop

1:10 pm - 6:11 pm

SXM

ORD

6h 01mnonstop

$655United Airlines

Sat, Oct 24 - Sat, Oct 31

8:45 am - 3:57 pm

ORD

SXM

5h 12mnonstop

2:52 pm - 11:42 pm

SXM

ORD

10h 50m

1 stop

$661United Airlines

Sat, Dec 5 - Fri, Dec 11

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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 18

ORD6:00 amChicago O'Hare Intl

7h 00m

1 stop

SXM2:00 pmSimpson Bay Princess Juliana

Sep 25

SXM3:05 pmSimpson Bay Princess Juliana

9h 03m

1 stop

ORD11:08 pmChicago O'Hare Intl

$372

JetBlue

Sep 14

ORD6:00 amChicago O'Hare Intl

7h 00m

1 stop

SXM2:00 pmSimpson Bay Princess Juliana

Sep 17

SXM3:05 pmSimpson Bay Princess Juliana

9h 03m

1 stop

ORD11:08 pmChicago O'Hare Intl

$375

JetBlue

Sep 19

ORD6:00 amChicago O'Hare Intl

7h 00m

1 stop

SXM2:00 pmSimpson Bay Princess Juliana

Sep 20

SXM3:05 pmSimpson Bay Princess Juliana

9h 03m

1 stop

ORD11:08 pmChicago O'Hare Intl

$405

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

Sep 11

ORD9:55 amChicago O'Hare Intl

30h 05m

1 stop

SXM5:00 pmSimpson Bay Princess Juliana

Sep 19

SXM6:00 pmSimpson Bay Princess Juliana

23h 58m

1 stop

ORD4:58 pmChicago O'Hare Intl

$409

Air Canada

Sep 11

ORD5:35 pmChicago O'Hare Intl

22h 25m

1 stop

SXM5:00 pmSimpson Bay Princess Juliana

Sep 19

SXM6:00 pmSimpson Bay Princess Juliana

27h 12m

2 stops

ORD8:12 pmChicago O'Hare Intl

$415

Air Canada

Oct 24

ORD5:35 pmChicago O'Hare Intl

20h 10m

1 stop

SXM2:45 pmSimpson Bay Princess Juliana

Oct 31

SXM2:40 pmSimpson Bay Princess Juliana

26h 12m

1 stop

ORD3:52 pmChicago O'Hare Intl

$416

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 9/26

6:00 am-2:00 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sat 10/3

3:05 pm-11:08 pm

1 stop9h 03m

$372

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 9/18

6:00 am-2:00 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Fri 9/25

3:05 pm-11:08 pm

1 stop9h 03m

$372

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 9/11

9:55 am-5:00 pm

1 stop30h 05m

Simpson Bay Princess Juliana

Sat 9/19

6:00 pm-4:58 pm

1 stop23h 58m

$409

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 9/11

5:35 pm-5:00 pm

1 stop22h 25m

Simpson Bay Princess Juliana

Sat 9/19

6:00 pm-8:12 pm

2 stops27h 12m

$415

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/26

6:00 am-2:00 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sat 10/3

6:00 pm-7:44 am

2 stops14h 44m

$416

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 9/18

6:21 pm-5:00 pm

2 stops21h 39m

Simpson Bay Princess Juliana

Fri 9/25

3:05 pm-11:08 pm

1 stop9h 03m

$424

Quickest round-trip

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 12/12

8:10 am-2:55 pm

Nonstop4h 45m

Simpson Bay Princess Juliana

Sat 12/19

2:30 pm-6:24 pm

Nonstop5h 54m

$650

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 11/28

7:50 pm-2:25 pm

1 stop16h 35m

Simpson Bay Princess Juliana

Sat 12/5

2:30 pm-6:24 pm

Nonstop5h 54m

$655

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/24

6:00 pm-12:50 pm

1 stop17h 50m

Simpson Bay Princess Juliana

Sat 10/31

1:10 pm-6:11 pm

Nonstop6h 01m

$655

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 12/5

8:45 am-3:57 pm

Nonstop5h 12m

Simpson Bay Princess Juliana

Fri 12/11

2:52 pm-11:42 pm

1 stop10h 50m

$661

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 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 $501.

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 $597. 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 $658 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 $505 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?

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	$745
Fastest flight time	4h 45m
Direct flights	Mon, Tue, Fri, Sat 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 $745

The fastest flight from Chicago O'Hare Intl Airport to St. Maarten takes 4h 45m

Direct flights go from Chicago O'Hare Intl Airport to St. Maarten on Monday, Tuesday, Friday, Saturday 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 August 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 44.44% of all bookings. The subsequent popular models are Airbus A319 at 24.44%, Boeing 737-700 at 13.33%, and Airbus A320-100/200 at 6.67%.

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 8,483 reviews	Search Delta flights
JetBlue	PriceFrom $389	Free Cancellation	Rating 7.2 3,026 reviews	Search JetBlue flights
United Airlines	PriceFrom $389	Free Cancellation	Rating 7.4 10,060 reviews	Search United Airlines flights
Air Canada	PriceFrom $487	Free Cancellation	Rating 7.1 11,424 reviews	Search Air Canada flights
American Airlines	PriceFrom $500	Free Cancellation	Rating 7.1 11,845 reviews	Search American Airlines 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 $347

Cheap flights from Chicago O'Hare Intl Airport to St. Maarten from $143

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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

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

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

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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Chicago O'Hare Intl Airport flight routes

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