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St. Maarten

$91+ Cheap flights from Chicago (CHI) 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Dec 16 — Dec 231
Tue 12/16
Tue 12/23
1 adult, Economy
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Find flight deals from Chicago to St. Maarten

Cheapest flights from Chicago to St. Maarten
Explore the most affordable flight options available from Chicago to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 16, 2025.

This Super.com deal was found by Cheapflights users on 11/14. 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 12/105:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Sat 12/133:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/14$219
This Super.com deal was found by Cheapflights users on 11/14. 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.
Mon 12/85:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Fri 12/123:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/14$257
This Priceline deal was found by Cheapflights users on 11/14. 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.
Sat 12/65:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Wed 12/103:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/14$261
This Cheapflightsfares deal was found by Cheapflights users on 11/15. 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.
Mon 12/155:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Mon 12/223:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 11/15$275
This Cheapflightsfares deal was found by Cheapflights users on 11/15. 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 11/295:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Sat 12/63:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/15$281
This Kiwi.com deal was found by Cheapflights users on 11/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:17 pmORD - SXM
2 stops42h 58mMultiple Airlines
Fri 12/123:20 pmSXM - ORD
1 stop10h 49mMultiple Airlines
Deal found 11/14$320
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:17 pmORD - SXM
2 stops42h 58mMultiple Airlines
Mon 12/223:20 pmSXM - ORD
1 stop21h 54mMultiple Airlines
Deal found 11/15$348
This Delta deal was found by Cheapflights users on 11/14. 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 11/156:00 amMDW - SXM
1 stop6h 55mDelta
Sun 11/164:20 pmSXM - MDW
1 stop9h 20mDelta
Deal found 11/14$457
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:23 pmMDW - SXM
2 stops40h 52mMultiple Airlines
Thu 12/184:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Deal found 11/13$489
This Delta deal was found by Cheapflights users on 11/13. 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.
Thu 12/116:00 amMDW - SXM
1 stop6h 28mDelta
Thu 12/181:45 pmSXM - MDW
1 stop12h 02mDelta
Deal found 11/13$592
This Delta deal was found by Cheapflights users on 11/14. 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 11/296:00 amMDW - SXM
1 stop6h 55mDelta
Sat 12/63:25 pmSXM - MDW
1 stop10h 22mDelta
Deal found 11/14$597
This Kissandfly.com deal was found by Cheapflights users on 11/14. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:00 amMDW - SXM
1 stop6h 55mKLM
Sat 12/63:25 pmSXM - MDW
2 stops23h 09mKLM
Deal found 11/14$630

Cheap flight deals from Chicago to St. Maarten

Keep the following information in mind while searching for Chicago to St. Maarten flight deals. Data was last updated November 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$219
(Super.com)

One-way from

$91
(Super.com)

Popular in

December

Cheapest in

August

Average price

$706

Good round-trip deal

$420 or less
Provider with most accurate pricing for Chicago (CHI)-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Simpson Bay Princess Juliana flights.
Search Deals
From Chicago (CHI) to St. Maarten
Search Deals
One-way flight from Chicago (CHI) to St. Maarten
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to St. Maarten.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 16, 2025.
Use the filters below to find and compare flights from Chicago to St. Maarten that are best for you.

Fly from

Chicago

Fly to

St. Maarten

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 12/8

5:00 am-2:15 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Fri 12/12

3:20 pm-12:09 am

1 stop10h 49m

$257

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 12/15

5:00 am-2:15 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Mon 12/22

3:20 pm-12:30 am

1 stop11h 10m

$275

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 1/15

8:22 pm-2:14 pm

1 stop15h 52m

Simpson Bay Princess Juliana

Sun 1/18

3:09 pm-11:46 pm

1 stop10h 37m

$291

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

2:40 pm-6:40 pm

Nonstop6h 00m

$363

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/21

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/28

4:30 pm-11:25 pm

1 stop8h 55m

$369

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/11

6:25 pm-12:30 pm

1 stop16h 05m

Simpson Bay Princess Juliana

Wed 1/14

4:20 pm-9:44 am

1 stop19h 24m

$377

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

Thu 1/15

4:20 pm-9:44 am

1 stop19h 24m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 1/12

6:25 pm-12:30 pm

1 stop16h 05m

Simpson Bay Princess Juliana

Fri 1/16

1:55 pm-11:57 pm

1 stop12h 02m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 2/9

7:56 pm-1:45 pm

1 stop15h 49m

Simpson Bay Princess Juliana

Wed 2/18

5:33 pm-7:24 am

2 stops15h 51m

$382

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 3/10

6:00 am-1:53 pm

1 stop6h 53m

Simpson Bay Princess Juliana

Wed 3/11

3:45 pm-12:35 pm

2 stops21h 50m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/15

Showing 1-10 of 32 results
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Best time to book a flight from Chicago to St. Maarten

Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Chicago 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 to St. Maarten

What is the cheapest month to book a flight from Chicago to St. Maarten?

Currently, September is the cheapest month in which you can book a flight from Chicago to St. Maarten (average of $312). Flying from Chicago 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 CHI to SX?

Find hourly flight availability from Chicago 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 16, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 47% on flights from Chicago to St. Maarten by exploring options for tickets at noon.

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 16, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Chicago to St. Maarten by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,010 reviews

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

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
8,010 reviews
Delta
7.9
Good
8,010 reviews

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

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
9,016 reviews
Delta
7.9
Good
8,010 reviews

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

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
11,051 reviews
Delta
7.9
Good
8,010 reviews

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

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
8,143 reviews
Delta
7.9
Good
8,010 reviews

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

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 Chicago 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 to St. Maarten?

    Departing from Chicago to St. Maarten will take you 5h 12m. There are 2204 mi between Chicago and St. Maarten. 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 to St. Maarten?

    Looking at all options, your cheapest flight can be booked for $366. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $219 on average, our data indicates $530 when flying from Chicago to St. Maarten.

  • Can I find deals for flights from Chicago to St. Maarten that include hotel bookings?

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

  • How can I find direct flights from Chicago to St. Maarten?

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

  • Can I find deals for business class flights from Chicago to St. Maarten?

    Yes. Cheapflights offers flight deals from Chicago 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 to St. Maarten?

    Currently, September is the cheapest month in which you can book a flight from Chicago to St. Maarten (average of $312). Flying from Chicago 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago 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 Chicago to St. Maarten

Discover the top 5 airlines that operate flights from Chicago 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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$318Average$706FlexibilityNo 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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