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St. Maarten

$125+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Find 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 November 3, 2025.

This Expedia deal was found by Cheapflights users on 11/1. 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 11/295:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Sat 12/63:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/1$302
This Priceline deal was found by Cheapflights users on 11/1. 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 12/155:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Wed 12/173:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/1$315
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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 12/135:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Sat 12/203:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 11/3$328
This United Airlines deal was found by Cheapflights users on 11/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:45 amORD - SXM
Nonstop5h 12mUnited Airlines
Sat 12/62:40 pmSXM - ORD
Nonstop6h 00mUnited Airlines
Deal found 11/1$361
This Delta deal was found by Cheapflights users on 11/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:02 pmORD - SXM
1 stop16h 53mDelta
Sat 12/63:25 pmSXM - ORD
1 stop9h 18mDelta
Deal found 11/2$365
This Delta deal was found by Cheapflights users on 11/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:30 amORD - SXM
1 stop6h 58mDelta
Tue 12/163:53 pmSXM - ORD
1 stop8h 50mDelta
Deal found 11/3$375
This Expedia deal was found by Cheapflights users on 11/1. 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 11/295:55 pmORD - SXM
2 stops44h 05mMultiple Airlines
Sat 12/63:20 pmSXM - ORD
1 stop10h 49mMultiple Airlines
Deal found 11/1$377
This Mytrip deal was found by Cheapflights users on 11/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:34 pmORD - SXM
2 stops16h 41mSpirit Airlines
Mon 11/173:20 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Deal found 11/1$378
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:07 pmORD - SXM
1 stop17h 13mAmerican Airlines
Sun 12/211:39 pmSXM - ORD
1 stop13h 04mAmerican Airlines
Deal found 11/2$380
This KAYAK deal was found by Cheapflights users on 11/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/175:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Fri 1/94:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 11/2$389

Cheap 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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$313
(Cheapflightsfares)

One-way from

$125
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$682

Good round-trip deal

$420 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
Highest demand for flights based on searches. 7% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip 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 November 3, 2025.
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 2/7

5:05 am-3:20 pm

1 stop8h 15m

Simpson Bay Princess Juliana

Wed 2/11

4:28 pm-11:42 pm

1 stop9h 14m

$329

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 11/29

8:02 pm-2:55 pm

1 stop16h 53m

Simpson Bay Princess Juliana

Sat 12/6

3:25 pm-1:50 pm

2 stops24h 25m

$365

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 11/29

8:45 am-3:57 pm

Nonstop5h 12m

Simpson Bay Princess Juliana

Sat 12/6

5:00 pm-11:43 pm

1 stop8h 43m

$371

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 12/16

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Tue 12/23

1:45 pm-12:02 am

1 stop12h 17m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 12/7

5:30 am-2:28 pm

1 stop6h 58m

Simpson Bay Princess Juliana

Tue 12/16

3:53 pm-10:43 pm

1 stop8h 50m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/7

8:45 am-3:57 pm

Nonstop5h 12m

Simpson Bay Princess Juliana

Wed 2/11

2:52 pm-10:59 pm

1 stop10h 07m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 1/5

5:33 am-2:55 pm

1 stop7h 22m

Simpson Bay Princess Juliana

Mon 1/12

4:20 pm-9:44 am

1 stop19h 24m

$381

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/4

6:15 pm-12:30 pm

1 stop16h 15m

Simpson Bay Princess Juliana

Mon 1/12

4:20 pm-9:44 am

1 stop19h 24m

$381

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 1/12

5:33 am-2:55 pm

1 stop7h 22m

Simpson Bay Princess Juliana

Sat 1/17

5:28 pm-11:57 pm

1 stop8h 29m

$381

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/10

5:05 am-3:20 pm

1 stop8h 15m

Simpson Bay Princess Juliana

Sat 1/17

4:30 pm-12:12 am

1 stop9h 42m

$395

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 19 results
1
2

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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to St. Maarten (average of $312). Flying from Chicago O'Hare Intl Airport to St. Maarten in June is currently the most expensive (average of $595). 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 November 3, 2025.

One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to St. Maarten is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 52% on airfare.

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 November 3, 2025.
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
8,002 reviews

Food

7.3

Overall

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

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
8,002 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Overall

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

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
8,997 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Overall

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

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
11,038 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Overall

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

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
8,115 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Overall

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

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 Delta and United Airlines fly from Chicago O'Hare Intl Airport to St. Maarten in about 5h 12m. The time it takes to get you to your destination can typically vary by up to 11h 41m. The distance from Chicago O'Hare Intl Airport to St. Maarten is about 2204 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $530, our data indicates the cheapest price to be $366. The most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana), is priced around $313.

  • 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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to St. Maarten (average of $312). Flying from Chicago O'Hare Intl Airport to St. Maarten in June is currently the most expensive (average of $595). 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 5 airlines flying from O'Hare Intl to St. Maarten

Discover the top 5 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$318Average$776FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$420Average$877FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$535Average$711FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$585Average$711FlexibilityNo cancel feeOn-time71%

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