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St. Maarten

$244+ Cheap flights from Midway (MDW) 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Midway to St. Maarten

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

Round-trip from

$375
(Frontier)

One-way from

$244
(Trip.com)

Popular in

December

Cheapest in

August

Average price

$612
From Chicago Midway to St. Maarten
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One-way flight from Chicago Midway 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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Find flight deals from Midway to St. Maarten

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

This Mytrip deal was found by Cheapflights users on 9/16. 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.
Mon 10/279:20 amMDW - SXM
2 stops28h 01mWestJet
Fri 10/313:20 pmSXM - MDW
2 stops22h 48mWestJet
Deal found 9/16$639
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
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.
Sat 11/16:00 amMDW - SXM
1 stop6h 49mDelta
Wed 11/54:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 9/15$762
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.
Sat 10/186:00 amMDW - SXM
1 stop6h 49mDelta
Sat 10/253:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 9/15$787
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.
Wed 11/511:00 amMDW - SXM
1 stop26h 21mMultiple Airlines
Tue 11/114:20 pmSXM - MDW
2 stops42h 52mMultiple Airlines
Deal found 9/15$811
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:00 amMDW - SXM
1 stop6h 49mDelta
Wed 11/54:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 9/14$832
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.
Fri 10/316:00 amMDW - SXM
1 stop6h 49mDelta
Fri 11/74:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 9/15$857
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.
Sun 10/266:00 amMDW - SXM
1 stop6h 49mDelta
Sat 11/13:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 9/15$897
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/216:00 amMDW - SXM
1 stop6h 50mDelta
Mon 9/293:20 pmSXM - MDW
2 stops22h 08mDelta
Deal found 9/14$902
This Delta 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 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 07mDelta
Deal found 9/14$922

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 Midway Airport to St. Maarten that are best for you.

Fly from

Midway

Fly to

St. Maarten

Route

Depart

Return

Price

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

MDW - SXM

MDWSXM

Chicago Midway

Sat 1/3

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 1/10

4:30 pm-11:25 pm

1 stop8h 55m

$568

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/28

4:30 pm-12:15 pm

2 stops17h 45m

Simpson Bay Princess Juliana

Wed 3/4

4:26 pm-12:35 pm

2 stops22h 09m

$624

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/28

4:30 pm-12:15 pm

2 stops17h 45m

Simpson Bay Princess Juliana

Thu 3/5

1:45 pm-9:46 pm

1 stop10h 01m

$624

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 3/3

6:00 am-2:56 pm

1 stop6h 56m

Simpson Bay Princess Juliana

Wed 3/4

4:26 pm-12:35 pm

2 stops22h 09m

$679

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/4

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Thu 1/8

1:45 pm-9:46 pm

1 stop10h 01m

$687

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 2/27

6:45 pm-2:15 pm

1 stop17h 30m

Simpson Bay Princess Juliana

Sat 3/7

5:16 pm-8:56 am

1 stop17h 40m

$689

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-4:25 pm

2 stops25h 40m

$692

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 1/24

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

$697

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 9/25

4:56 pm-2:00 pm

2 stops20h 04m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 18 results
1
2

Best time to book a flight from Midway to St. Maarten

Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Midway 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 Midway Airport to St. Maarten
No data available for this route at this time. Please check back soon.

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 from Chicago Midway Airport 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

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

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

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

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 Midway 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 Midway Airport to St. Maarten?

    There are many flights that can get you from Chicago Midway Airport to St. Maarten in 7h 20m. Fly via Frontier or Delta to get the fastest option. The distance from Chicago Midway Airport to St. Maarten is about 2189 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway 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 Midway Airport to St. Maarten?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to St. Maarten (average of $459). Flying from Chicago Midway Airport 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 Midway to St. Maarten

See prices for flight routes from nearby airports that may be better suited for you.
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O'Hare Intl to The Valley flights
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Midway to St. John's flights
O'Hare Intl to Gustavia flights

Top airline flying from Midway to St. Maarten

Discover the top airline that operate flights from Midway 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
DeltaCheapest$622Average$637FlexibilityNo cancel feeOn-timeN/A

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