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Saint Martin Island

$111+ Cheap flights from Midway (MDW) to Saint Martin Island

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 12/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Cheap flight deals from Midway to Saint Martin Island

Keep the following information in mind while searching for Midway to Saint Martin Island flight deals. Data was last updated November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$308
(Frontier)

One-way from

$111
(Priceline)

Popular in

December

Cheapest in

August

Average price

$706
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 Saint Martin Island
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One-way flight from Chicago Midway to Saint Martin Island
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Highest demand for flights based on searches. 9% potential increase in price ($72 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 November 2025
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Find flight deals from Midway to Saint Martin Island

Cheapest flights from Midway to Saint Martin Island
Explore the most affordable flight options available from Midway to Saint Martin Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2025.

This Delta deal was found by Cheapflights users on 11/20. 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 12/136:00 amMDW - SXM
1 stop6h 50mDelta
Sat 12/205:22 pmSXM - MDW
1 stop17h 43mDelta
Deal found 11/20$368
This Delta deal was found by Cheapflights users on 11/19. 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 12/216:00 amMDW - SXM
1 stop6h 50mDelta
Tue 12/301:45 pmSXM - MDW
1 stop10h 37mDelta
Deal found 11/19$377
This Delta deal was found by Cheapflights users on 11/19. 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 12/216:00 amMDW - SXM
1 stop6h 50mDelta
Mon 12/294:15 pmSXM - MDW
2 stops20h 51mDelta
Deal found 11/19$382
This Delta deal was found by Cheapflights users on 11/20. 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
Tue 12/301:45 pmSXM - MDW
1 stop10h 37mDelta
Deal found 11/20$457
This Delta deal was found by Cheapflights users on 11/19. 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 55mDelta
Thu 11/274:20 pmSXM - MDW
1 stop9h 20mDelta
Deal found 11/19$487
This Delta deal was found by Cheapflights users on 11/19. 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 12/265:59 pmMDW - SXM
1 stop18h 18mDelta
Tue 12/301:45 pmSXM - MDW
1 stop10h 37mDelta
Deal found 11/19$507
This Delta deal was found by Cheapflights users on 11/19. 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 12/265:59 pmMDW - SXM
1 stop18h 18mDelta
Mon 12/294:15 pmSXM - MDW
2 stops27h 11mDelta
Deal found 11/19$512
This Delta deal was found by Cheapflights users on 11/19. 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 12/216:00 amMDW - SXM
1 stop6h 50mDelta
Wed 12/314:15 pmSXM - MDW
2 stops27h 11mDelta
Deal found 11/19$527
This Delta deal was found by Cheapflights users on 11/20. 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 12/96:00 amMDW - SXM
1 stop6h 28mDelta
Tue 12/163:53 pmSXM - MDW
1 stop9h 54mDelta
Deal found 11/20$536

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Saint Martin Island 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 November 20, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Saint Martin Island that are best for you.

Fly from

Midway

Fly to

Saint Martin Island

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

Thu 1/29

1:55 pm-10:22 pm

1 stop10h 27m

$355

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 1/13

6:14 pm-2:55 pm

2 stops18h 41m

Simpson Bay Princess Juliana

Fri 1/16

1:55 pm-10:07 pm

1 stop10h 12m

$360

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 1/7

1:28 pm-12:30 pm

2 stops21h 02m

Simpson Bay Princess Juliana

Fri 1/16

1:55 pm-10:07 pm

1 stop10h 12m

$360

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/11

1:49 pm-12:30 pm

2 stops20h 41m

Simpson Bay Princess Juliana

Thu 1/15

1:55 pm-10:07 pm

1 stop10h 12m

$360

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/11

5:31 pm-12:30 pm

2 stops16h 59m

Simpson Bay Princess Juliana

Wed 1/14

1:55 pm-10:07 pm

1 stop10h 12m

$360

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 1/12

5:31 pm-12:30 pm

2 stops16h 59m

Simpson Bay Princess Juliana

Fri 1/16

1:55 pm-10:07 pm

1 stop10h 12m

$360

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 1/28

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 2/6

1:55 pm-10:22 pm

1 stop10h 27m

$377

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 12/21

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Mon 12/29

1:45 pm-10:22 pm

1 stop10h 37m

$377

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 12/19

6:12 am-1:30 pm

1 stop29h 18m

$111

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 12/19

8:15 am-2:15 pm

2 stops28h 00m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 14 results
1
2

Best time to book a flight from Midway to Saint Martin Island

Have a flexible travel schedule? Discover the best time to fly to Saint Martin Island 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 Saint Martin Island
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Saint Martin Island

Get insights into the airlines that provide service to Saint Martin Island. 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 Saint Martin Island. Reviews last updated November 20, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Saint Martin Island, such as Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,002 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.1

Overall

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
8,002 reviews
Delta
7.9
Good
8,002 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.1

Overall

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 Saint Martin Island. 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 Saint Martin Island?

    Departing from Chicago Midway Airport to Saint Martin Island will take you 6h 55m. The distance from Chicago Midway Airport to Saint Martin Island is about 2189 mi.

  • Can I find deals for flights from Midway to Saint Martin Island that include hotel bookings?

    Yes. In addition to deals on Midway to Saint Martin Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Saint Martin Island?

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

  • Can I find deals for business class flights from Midway to Saint Martin Island?

    Yes. Cheapflights offers flight deals from Midway to Saint Martin Island 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

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Alternative routes for Midway to Saint Martin Island

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 Saint Martin Island

Discover the top airline that operate flights from Midway to Saint Martin Island. 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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$622Average$637FlexibilityNo cancel feeOn-timeN/A

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