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St. Maarten

$158+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
juin 17 — juin 241
mar. 6/17
mar. 6/24
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 juin 12, 2025.

Round-trip from

$313
(Priceline)

One-way from

$158
(SmartFares)

Popular in

March

Cheapest in

September

Average price

$755

Good round-trip deal

$622 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. 5% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in June 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 juin 12, 2025.

This Priceline deal was found by Cheapflights users on 6/11. 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.
ven. 9/58:34 amMDW - SXM
1 stop26h 51mFrontier
sam. 9/131:58 pmSXM - MDW
1 stop18h 41mFrontier
Deal found 6/11$313
This Priceline deal was found by Cheapflights users on 6/11. 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.
ven. 9/56:10 amORD - SXM
1 stop29h 15mFrontier
sam. 9/131:58 pmSXM - ORD
1 stop23h 59mFrontier
Deal found 6/11$313
This Booking.com deal was found by Cheapflights users on 6/10. 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.
sam. 9/65:05 amORD - SXM
1 stop8h 19mMultiple Airlines
sam. 9/131:58 pmSXM - ORD
1 stop23h 59mMultiple Airlines
Deal found 6/10$366
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
mer. 7/165:05 amORD - SXM
1 stop7h 55mSpirit Airlines
sam. 7/263:05 pmSXM - ORD
1 stop9h 48mSpirit Airlines
Deal found 6/10$377
This FlightHub deal was found by Cheapflights users on 6/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 12/48:25 pmORD - SXM
1 stop17h 50mAir Canada
sam. 12/135:15 pmSXM - ORD
1 stop19h 43mAir Canada
Deal found 6/11$530
This Delta deal was found by Cheapflights users on 6/10. 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.
mer. 7/95:35 amORD - SXM
1 stop7h 21mDelta
mar. 7/153:21 pmSXM - ORD
1 stop9h 48mDelta
Deal found 6/10$587
This Delta deal was found by Cheapflights users on 6/10. 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.
sam. 9/136:00 amMDW - SXM
1 stop6h 50mDelta
ven. 9/193:15 pmSXM - MDW
1 stop7h 29mDelta
Deal found 6/10$612
This American Airlines deal was found by Cheapflights users on 6/11. 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.
sam. 10/186:55 pmORD - SXM
1 stop17h 20mAmerican Airlines
sam. 10/252:40 pmSXM - ORD
1 stop8h 54mAmerican Airlines
Deal found 6/11$612
This Mytrip deal was found by Cheapflights users on 6/10. 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.
ven. 7/410:31 amMDW - SXM
2 stops26h 29mMultiple Airlines
lun. 7/73:05 pmSXM - MDW
3 stops26h 19mMultiple Airlines
Deal found 6/10$767
This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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.
sam. 11/222:00 pmMDW - SXM
2 stops23h 17mWestJet
jeu. 11/274:10 pmSXM - MDW
2 stops22h 59mWestJet
Deal found 6/12$3,363

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 juin 12, 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

MDW - SXM

MDWSXM

Chicago Midway

ven. 9/5

8:34 am-12:25 pm

1 stop26h 51m

Simpson Bay Princess Juliana

sam. 9/13

1:58 pm-7:39 am

1 stop18h 41m

$313

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

ven. 9/5

6:10 am-12:25 pm

1 stop29h 15m

Simpson Bay Princess Juliana

sam. 9/13

1:58 pm-12:57 pm

1 stop23h 59m

$313

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

sam. 9/6

5:05 am-2:24 pm

1 stop8h 19m

Simpson Bay Princess Juliana

sam. 9/13

1:58 pm-12:57 pm

1 stop23h 59m

$366

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

mer. 7/16

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

sam. 7/26

3:05 pm-11:53 pm

1 stop9h 48m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

jeu. 12/4

8:25 pm-4:15 pm

1 stop17h 50m

Simpson Bay Princess Juliana

sam. 12/13

5:15 pm-10:58 am

1 stop19h 43m

$530

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

mer. 7/9

5:35 am-1:56 pm

1 stop7h 21m

Simpson Bay Princess Juliana

mar. 7/15

3:21 pm-12:09 am

1 stop9h 48m

$587

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

sam. 10/18

6:55 pm-1:15 pm

1 stop17h 20m

Simpson Bay Princess Juliana

sam. 10/25

2:40 pm-10:34 pm

1 stop8h 54m

$612

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

sam. 9/13

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

ven. 9/19

3:15 pm-9:44 pm

1 stop7h 29m

$612

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

ven. 7/4

10:31 am-2:00 pm

2 stops26h 29m

Simpson Bay Princess Juliana

lun. 7/7

3:05 pm-4:24 pm

3 stops26h 19m

$767

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

sam. 11/22

2:00 pm-3:17 pm

2 stops23h 17m

Simpson Bay Princess Juliana

jeu. 11/27

4:10 pm-1:09 pm

2 stops22h 59m

$3,363

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 18 results
1
2

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 $657). 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 juin 12, 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 juin 12, 2025.
See what other customers who have flown with Delta, Copa Airlines and American Airlines from Chicago to St. Maarten have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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!
Copa Airlines
7.5
Good
1,451 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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!
WestJet
7.2
Good
2,868 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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!
Air Canada
7.1
Good
9,531 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

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 airlines to fly from Chicago to St. Maarten one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $158. Frontier flights start at $163 while deals on American Airlines start at $293 one-way.

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

    Looking at all options, your cheapest flight can be booked for $607. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $366 on average our data indicates $707 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 $657). 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 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 juin 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$330Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$554Average$721FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$615Average$707FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$654Average$912FlexibilityNo cancel feeOn-time69%

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