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St. Maarten

$140+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$337
(Cheapflightsfares)

One-way from

$140
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$612

Good round-trip deal

$642 or less

Good one-way deal

$368 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. 8% potential increase in price ($72 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 September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to St. Maarten.
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Price to beat on a one-way 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 September 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 11/15:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Wed 11/54:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 9/15$337
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Fri 10/35:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Fri 10/103:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 9/15$342
This Priceline deal was found by Cheapflights users on 9/14. 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 11/85:05 amORD - SXM
1 stop8h 05mSpirit Airlines
Sat 11/154:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 9/14$347
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/185:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 10/253:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 9/15$367
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/42:00 pmORD - SXM
1 stop24h 00mMultiple Airlines
Wed 12/104:28 pmSXM - ORD
1 stop9h 14mMultiple Airlines
Deal found 9/15$373
This Mytrip deal was found by Cheapflights users on 9/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/291:59 pmORD - SXM
2 stops48h 01mMultiple Airlines
Wed 11/54:28 pmSXM - ORD
1 stop9h 14mMultiple Airlines
Deal found 9/14$383
This Orbitz deal was found by Cheapflights users on 9/14. 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 Orbitz 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
Wed 12/34:28 pmSXM - ORD
1 stop9h 14mMultiple Airlines
Deal found 9/14$393
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sun 10/267:43 pmORD - SXM
1 stop17h 17mSpirit Airlines
Sat 11/13:05 pmSXM - ORD
1 stop21h 45mSpirit Airlines
Deal found 9/15$398
This Priceline deal was found by Cheapflights users on 9/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/317:43 pmORD - SXM
1 stop17h 17mMultiple Airlines
Fri 11/75:00 pmSXM - ORD
2 stops20h 18mMultiple Airlines
Deal found 9/15$401
This Gotogate deal was found by Cheapflights users on 9/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:43 pmORD - SXM
1 stop17h 17mMultiple Airlines
Sat 11/14:00 pmSXM - ORD
2 stops21h 18mMultiple Airlines
Deal found 9/15$402
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/237:43 pmORD - SXM
1 stop17h 17mMultiple Airlines
Sun 10/2612:25 pmSXM - ORD
2 stops21h 57mMultiple Airlines
Deal found 9/15$407
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/196:00 amMDW - SXM
1 stop6h 55mDelta
Sun 11/234:20 pmSXM - MDW
1 stop9h 12mDelta
Deal found 9/15$757

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 September 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

Sat 1/24

5:05 am-3:20 pm

1 stop8h 15m

Simpson Bay Princess Juliana

Sat 1/31

4:30 pm-11:35 pm

1 stop9h 05m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 10/29

1:59 pm-3:00 pm

2 stops48h 01m

Simpson Bay Princess Juliana

Wed 11/5

4:28 pm-11:42 pm

1 stop9h 14m

$383

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 10/31

7:43 pm-2:00 pm

1 stop17h 17m

Simpson Bay Princess Juliana

Fri 11/7

5:00 pm-11:18 am

2 stops20h 18m

$401

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 1/26

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Mon 2/2

4:28 pm-9:23 am

1 stop18h 55m

$435

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 1/10

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 1/17

4:30 pm-11:26 pm

1 stop8h 56m

$439

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 2/3

5:59 pm-3:10 pm

1 stop19h 11m

Simpson Bay Princess Juliana

Fri 2/6

4:28 pm-11:42 pm

1 stop9h 14m

$440

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 1/26

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Thu 2/5

12:25 pm-12:30 pm

2 stops26h 05m

$474

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/11

6:28 pm-4:00 pm

1 stop19h 32m

Simpson Bay Princess Juliana

Mon 12/15

5:00 pm-11:18 am

2 stops20h 18m

$483

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/24

2:13 pm-11:24 am

1 stop19h 11m

Simpson Bay Princess Juliana

Sun 2/1

12:25 pm-12:04 am

1 stop13h 39m

$489

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/1

7:00 am-1:37 pm

1 stop28h 37m

Simpson Bay Princess Juliana

Fri 3/6

5:13 pm-8:54 am

1 stop17h 41m

$496

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 36 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 $652). 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 September 16, 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 September 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
8.0
Very good
7,957 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

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
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

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
8,924 reviews
Delta
8.0
Very good
7,957 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

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
7,957 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

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
8,019 reviews
Delta
8.0
Very good
7,957 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

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.

  • How long is the flight from Chicago to St. Maarten?

    Departing from Chicago to St. Maarten will take you 8h 05m. 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 $313. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $337 on average, our data indicates $585 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 $652). 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.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Punta Cana flights
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O'Hare Intl to Oranjestad flights
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Midway to Punta Cana flights
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O'Hare Intl to Providenciales flights
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O'Hare Intl to Willemstad flights
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O'Hare Intl to Santo Domingo flights
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St. Louis to Montego Bay flights
Midway to Nassau flights
O'Hare Intl to Bridgetown flights
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St. Louis to Georgetown flights
O'Hare Intl to Christiansted flights
O'Hare Intl to St. John's flights
O'Hare Intl to Kingston flights
O'Hare Intl to Puerto Plata flights
St. Louis to Nassau flights
Midway to Simpson Bay flights
Midway to George Town flights
St. Louis to Simpson Bay flights
Midway to Santo Domingo flights
O'Hare Intl to Kralendijk flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to Road Town flights
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Midway to Castries flights
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St. Louis to Santo Domingo flights
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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$318Average$721FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$619Average$713FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$647Average$908FlexibilityNo cancel feeOn-time69%

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