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St. Maarten

$93+ Cheap flights from O'Hare Intl (ORD) to St. Maarten

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Mar 23 — Mar 301
Mon 3/23
Mon 3/30
1 adult, Economy
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Cheap flight deals from O'Hare Intl to St. Maarten

Cheapest flights from O'Hare Intl to St. Maarten
Explore the most affordable flight options available from O'Hare Intl to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 21, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Tue 3/172:20 pm
SXM
-
ORD
1 stop9h 57m
Spirit Airlines
Deal found 2/18$304
This Cheapflightsfares deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/255:05 am
ORD
-
SXM
1 stop7h 25m
Spirit Airlines
Sat 5/92:35 pm
SXM
-
ORD
1 stop10h 39m
Spirit Airlines
Deal found 2/18$309
This Booking.com deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:05 am
ORD
-
SXM
1 stop7h 25m
Spirit Airlines
Thu 4/162:35 pm
SXM
-
ORD
1 stop10h 39m
Spirit Airlines
Deal found 2/18$314
This Priceline deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:05 am
ORD
-
SXM
1 stop7h 25m
Spirit Airlines
Fri 5/12:35 pm
SXM
-
ORD
1 stop10h 39m
Spirit Airlines
Deal found 2/18$315
This Cheapflightsfares deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:05 am
ORD
-
SXM
1 stop7h 10m
Spirit Airlines
Tue 3/242:20 pm
SXM
-
ORD
1 stop9h 57m
Spirit Airlines
Deal found 2/21$317
This Cheapflightsfares deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/195:05 am
ORD
-
SXM
1 stop7h 25m
Spirit Airlines
Fri 4/242:35 pm
SXM
-
ORD
1 stop10h 39m
Spirit Airlines
Deal found 2/20$319
This Cheapflightsfares deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/68:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Tue 3/102:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/21$321
This Cheapflightsfares deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/58:16 pm
ORD
-
SXM
1 stop15h 59m
Spirit Airlines
Mon 3/92:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/18$323
This Super.com deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Mon 3/92:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/18$324
This Cheapflightsfares deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/255:34 pm
ORD
-
SXM
1 stop18h 56m
Spirit Airlines
Fri 5/12:35 pm
SXM
-
ORD
1 stop10h 39m
Spirit Airlines
Deal found 2/19$332
This Expedia deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:30 am
ORD
-
SXM
1 stop8h 05m
Multiple Airlines
Thu 4/162:35 pm
SXM
-
ORD
1 stop10h 39m
Multiple Airlines
Deal found 2/17$334

Find flight deals from O'Hare Intl to St. Maarten

Keep the following information in mind while searching for O'Hare Intl to St. Maarten flight deals. Data was last updated February 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$304
(Cheapflightsfares)

One-way from

$93
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$607

Good round-trip deal

$706 or less

Good one-way deal

$304 or less
Provider with most accurate pricing for Chicago (CHI)-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Simpson Bay Princess Juliana flights.
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From Chicago O'Hare Intl to St. Maarten
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One-way flight from Chicago O'Hare Intl to St. Maarten
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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Price to beat on a round-trip flight from Chicago O'Hare Intl to St. Maarten.
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Price to beat on a one-way flight from Chicago O'Hare Intl to St. Maarten.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to St. Maarten that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 21, 2026.
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

O'Hare Intl

Fly to

St. Maarten

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 5/2

5:34 pm-1:30 pm

1 stop18h 56m

Simpson Bay Princess Juliana

Sat 5/9

2:35 pm-12:14 am

1 stop10h 39m

$347

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 3/5

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Mon 3/16

2:20 pm-10:36 am

1 stop21h 16m

$351

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 3/7

8:16 pm-1:15 pm

1 stop14h 59m

Simpson Bay Princess Juliana

Sat 3/14

2:35 pm-10:52 am

1 stop21h 17m

$374

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/18

5:09 pm-1:30 pm

3 stops19h 21m

Simpson Bay Princess Juliana

Sat 4/25

2:35 pm-12:14 am

1 stop10h 39m

$400

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 4/30

5:05 am-1:30 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Fri 5/15

2:35 pm-9:17 pm

1 stop31h 42m

$400

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/4

1:55 pm-1:35 pm

2 stops22h 40m

Simpson Bay Princess Juliana

Mon 4/6

4:00 pm-10:53 am

2 stops19h 53m

$401

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 4/1

5:05 am-1:30 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Wed 4/8

2:35 pm-12:22 am

3 stops34h 47m

$406

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 3/14

6:10 pm-1:15 pm

1 stop18h 05m

Simpson Bay Princess Juliana

Wed 3/18

2:20 pm-11:17 pm

1 stop9h 57m

$407

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 4/16

7:20 pm-1:30 pm

2 stops17h 10m

Simpson Bay Princess Juliana

Mon 4/20

2:35 pm-9:17 pm

1 stop31h 42m

$427

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 5/16

5:05 am-1:30 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Sat 5/23

2:55 pm-12:11 pm

2 stops22h 16m

$428

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 21 results
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Best time to book a flight from O'Hare Intl to St. Maarten

Have a flexible travel schedule? Discover the best time to fly to St. Maarten from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to St. Maarten

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to St. Maarten?

Currently, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to St. Maarten (average of $231). Flying from Chicago O'Hare Intl Airport to St. Maarten in June is currently the most expensive (average of $597). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to SX?

Find hourly flight availability from O'Hare Intl to St. Maarten. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 21, 2026.

When flying from Chicago O'Hare Intl Airport to St. Maarten, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

About 28% of weekly flights between Chicago and St. Maarten have experienced delays in the past year, with the average delay time being 96 minutes.

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

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

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

Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

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

Over the last year, American Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.

Reviews of airlines servicing St. Maarten

Get insights into the airlines that provide service to St. Maarten. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to St. Maarten. Reviews last updated February 21, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to St. Maarten, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,228 reviews

Comfort

7.9

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,228 reviews
Delta
7.9
Good
8,228 reviews

Comfort

7.9

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,335 reviews
Delta
7.9
Good
8,228 reviews

Comfort

7.9

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,334 reviews
Delta
7.9
Good
8,228 reviews

Comfort

7.9

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,898 reviews
Delta
7.9
Good
8,228 reviews

Comfort

7.9

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,482 reviews
Delta
7.9
Good
8,228 reviews

Comfort

7.9

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to St. Maarten. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago O'Hare Intl Airport to St. Maarten?

    Airlines like Spirit Airlines fly from Chicago O'Hare Intl Airport to St. Maarten in about 18h 56m. The time it takes to get you to your destination can typically vary by up to . The distance from Chicago O'Hare Intl Airport to St. Maarten is about 2204 mi.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to St. Maarten?

    Looking for the cheapest flight from Chicago O'Hare Intl Airport to St. Maarten? While on average our users pay $686, our data indicates the cheapest price to be $554. The most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana), is priced around $309.

  • Can I find deals for flights from O'Hare Intl to St. Maarten that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to St. Maarten flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to St. Maarten?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to St. Maarten.

  • Can I find deals for business class flights from O'Hare Intl to St. Maarten?

    Yes. Cheapflights offers flight deals from O'Hare Intl to St. Maarten by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to St. Maarten?

    Currently, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to St. Maarten (average of $231). Flying from Chicago O'Hare Intl Airport to St. Maarten in June is currently the most expensive (average of $597). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for O'Hare Intl to St. Maarten

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from O'Hare Intl to St. Maarten

Discover the top 6 airlines that operate flights from O'Hare Intl to St. Maarten. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$231Average$382FlexibilityNo cancel feeOn-time65%
DeltaCheapest$290Average$392FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$389Average$748FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$487Average$617FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$501Average$677FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$568Average$731FlexibilityNo cancel feeOn-time62%

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