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St. Maarten

$310+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Delta deal was found by Cheapflights users on 12/15. 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.
Tue 12/166:00 amMDW - SXM
1 stop6h 28mDelta
Tue 12/231:45 pmSXM - MDW
1 stop10h 37mDelta
Deal found 12/15$501
This Delta deal was found by Cheapflights users on 12/15. 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 12/246:00 amMDW - SXM
1 stop6h 50mDelta
Mon 12/291:45 pmSXM - MDW
1 stop10h 37mDelta
Deal found 12/15$709
This Delta deal was found by Cheapflights users on 12/17. 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 12/206:00 amMDW - SXM
1 stop7h 57mDelta
Sat 12/271:45 pmSXM - MDW
1 stop10h 37mDelta
Deal found 12/17$966
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:12 amMDW - SXM
2 stops30h 03mMultiple Airlines
Wed 12/314:20 pmSXM - MDW
1 stop25h 00mMultiple Airlines
Deal found 12/16$1,139
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/154:15 pmMDW - SXM
1 stop21h 06mMultiple Airlines
Mon 12/224:20 pmSXM - MDW
1 stop25h 00mMultiple Airlines
Deal found 12/14$1,375
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Sat 12/204:15 pmMDW - SXM
1 stop21h 06mMultiple Airlines
Sat 12/276:10 pmSXM - MDW
2 stops45h 55mMultiple Airlines
Deal found 12/14$1,423
This Delta deal was found by Cheapflights users on 12/17. 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 12/276:00 amMDW - SXM
1 stop6h 50mDelta
Thu 1/11:45 pmSXM - MDW
1 stop10h 37mDelta
Deal found 12/17$1,875

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$356
(Frontier)

One-way from

$310
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$988
Provider with most accurate pricing for Chicago (CHI)-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Simpson Bay Princess Juliana flights.
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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. 7% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 December 18, 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

Sun 1/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Wed 1/28

1:55 pm-10:22 pm

1 stop10h 27m

$501

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 4/4

6:00 am-2:40 pm

1 stop7h 40m

Simpson Bay Princess Juliana

Sat 4/11

3:40 pm-11:42 pm

1 stop9h 02m

$576

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 1/30

1:55 pm-10:22 pm

1 stop10h 27m

$581

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 4/29

6:00 am-2:09 pm

1 stop7h 09m

Simpson Bay Princess Juliana

Tue 5/5

1:50 pm-9:45 pm

1 stop8h 55m

$584

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 2/17

1:28 pm-12:13 pm

2 stops20h 45m

Simpson Bay Princess Juliana

Tue 2/24

1:38 pm-10:44 pm

1 stop11h 06m

$586

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 3/18

1:09 pm-11:30 am

2 stops21h 21m

Simpson Bay Princess Juliana

Wed 3/25

3:45 pm-1:23 pm

2 stops22h 38m

$589

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 3/16

2:03 pm-11:30 am

2 stops20h 27m

Simpson Bay Princess Juliana

Wed 3/25

3:45 pm-12:29 pm

2 stops21h 44m

$589

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 1/2

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Wed 1/7

1:55 pm-10:07 pm

1 stop10h 12m

$651

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/25

4:15 pm-11:55 am

2 stops17h 40m

Simpson Bay Princess Juliana

Wed 1/28

4:20 pm-10:10 am

1 stop19h 50m

$654

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 3/21

2:03 pm-11:30 am

2 stops20h 27m

Simpson Bay Princess Juliana

Wed 3/25

3:45 pm-12:29 pm

2 stops21h 44m

$659

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 16 results
1
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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 December 18, 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
7.9
Good
8,005 reviews

Food

7.3

Boarding

8.1

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

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
8,005 reviews
Delta
7.9
Good
8,005 reviews

Food

7.3

Boarding

8.1

Entertainment

7.9

Crew

8.5

Overall

7.9

Comfort

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 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 6h 55m. Fly via Delta or Frontier 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.

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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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$512Average$637FlexibilityNo cancel feeOn-timeN/A

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