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St. Maarten

$139+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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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 August 14, 2025.

Round-trip from

$317
(Cheapflightsfares)

One-way from

$139
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$637

Good round-trip deal

$882 or less
From Chicago (CHI) to St. Maarten
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One-way flight from Chicago (CHI) to St. Maarten
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Highest demand for flights based on searches. 10% potential increase in price ($81 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago (CHI) to St. Maarten.
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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 August 14, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/65:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 9/203:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/13$317
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 9/35:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 9/63:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/12$337
This Priceline deal was found by Cheapflights users on 8/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/275:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 10/43:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/13$342
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/185:05 amORD - SXM
1 stop7h 54mSpirit Airlines
Sat 11/13:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Deal found 8/13$351
This Priceline deal was found by Cheapflights users on 8/14. 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.
Tue 9/28:12 pmORD - SXM
1 stop16h 48mSpirit Airlines
Sat 9/203:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/14$367
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/116:44 pmORD - SXM
1 stop18h 16mSpirit Airlines
Mon 9/153:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/13$369
This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:29 pmORD - SXM
1 stop17h 30mSpirit Airlines
Mon 10/273:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Deal found 8/14$387
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/295:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Fri 9/53:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/13$396
This Delta deal was found by Cheapflights users on 8/14. 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.
Wed 11/266:00 amMDW - SXM
1 stop6h 35mDelta
Wed 12/34:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 8/14$667
This Delta deal was found by Cheapflights users on 8/13. 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 35mDelta
Tue 12/164:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 8/13$782
This Delta deal was found by Cheapflights users on 8/13. 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.
Fri 11/286:00 amMDW - SXM
1 stop6h 35mDelta
Sat 12/64:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 8/13$807
This Delta deal was found by Cheapflights users on 8/14. 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.
Wed 11/56:00 amMDW - SXM
1 stop6h 49mDelta
Tue 11/114:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 8/14$847

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 August 14, 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

Sat 9/6

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 9/20

3:05 pm-10:48 pm

1 stop8h 43m

$317

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 9/3

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-10:48 pm

1 stop8h 43m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/18

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Sat 10/25

3:05 pm-11:45 pm

1 stop9h 40m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/27

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 10/4

3:05 pm-10:48 pm

1 stop8h 43m

$342

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/18

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Sat 11/1

3:05 pm-1:03 am

1 stop10h 58m

$351

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 9/2

8:12 pm-2:00 pm

1 stop16h 48m

Simpson Bay Princess Juliana

Sat 9/20

3:05 pm-10:48 pm

1 stop8h 43m

$367

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 9/11

6:44 pm-2:00 pm

1 stop18h 16m

Simpson Bay Princess Juliana

Mon 9/15

3:05 pm-10:48 pm

1 stop8h 43m

$369

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 10/23

7:29 pm-1:59 pm

1 stop17h 30m

Simpson Bay Princess Juliana

Mon 10/27

3:05 pm-1:03 am

1 stop10h 58m

$387

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 8/29

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Fri 9/5

3:05 pm-10:48 pm

1 stop8h 43m

$396

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/25

6:00 am-2:56 pm

1 stop6h 56m

Simpson Bay Princess Juliana

Sun 2/1

1:45 pm-9:46 pm

1 stop10h 01m

$612

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

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 $459). Flying from Chicago to St. Maarten in March is currently the most expensive (average of $654). 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 August 14, 2025.

When flying from Chicago 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.

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 August 14, 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
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,916 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,045 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest flights from Chicago to St. Maarten?

    Looking at all options, your cheapest flight can be booked for $732. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $317 on average our data indicates $882 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 $459). Flying from Chicago to St. Maarten in March is currently the most expensive (average of $654). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 4 airlines flying from Chicago to St. Maarten

Discover the top 4 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$333Average$401FlexibilityNo cancel feeOn-time65%
DeltaCheapest$564Average$721FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$614Average$713FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$654Average$911FlexibilityNo cancel feeOn-time69%

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