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Saint Martin Island

$95+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
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 January 12, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$431
(Frontier)

One-way from

$95
(Trip.com)

Popular in

December

Cheapest in

February

Average price

$612
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. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 12, 2026.

This Frontier deal was found by Cheapflights users on 1/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:00 am
MDW
-
SXM
1 stop7h 40m
Frontier
Sat 4/113:40 pm
SXM
-
MDW
1 stop9h 02m
Frontier
Deal found 1/12$431
This Delta deal was found by Cheapflights users on 1/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/96:00 am
MDW
-
SXM
1 stop6h 55m
Delta
Wed 2/181:38 pm
SXM
-
MDW
1 stop10h 53m
Delta
Deal found 1/11$509
This Delta deal was found by Cheapflights users on 1/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/96:35 pm
MDW
-
SXM
2 stops15h 55m
Delta
Tue 2/171:38 pm
SXM
-
MDW
1 stop10h 55m
Delta
Deal found 1/12$514
This Delta deal was found by Cheapflights users on 1/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/266:00 am
MDW
-
SXM
1 stop6h 55m
Delta
Thu 1/291:55 pm
SXM
-
MDW
1 stop10h 27m
Delta
Deal found 1/12$519
This Delta deal was found by Cheapflights users on 1/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/186:00 am
MDW
-
SXM
1 stop6h 50m
Delta
Wed 2/251:38 pm
SXM
-
MDW
1 stop10h 53m
Delta
Deal found 1/12$529
This Delta deal was found by Cheapflights users on 1/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/96:00 am
MDW
-
SXM
1 stop6h 55m
Delta
Sat 2/141:38 pm
SXM
-
MDW
1 stop10h 53m
Delta
Deal found 1/11$539
This Delta deal was found by Cheapflights users on 1/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/106:00 am
MDW
-
SXM
1 stop6h 55m
Delta
Sun 2/152:50 pm
SXM
-
MDW
2 stops23h 56m
Delta
Deal found 1/12$544
This Delta deal was found by Cheapflights users on 1/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:00 am
MDW
-
SXM
1 stop6h 50m
Delta
Wed 3/41:38 pm
SXM
-
MDW
1 stop10h 53m
Delta
Deal found 1/11$552
This Delta deal was found by Cheapflights users on 1/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/316:25 am
MDW
-
SXM
1 stop7h 38m
Delta
Sat 2/75:28 pm
SXM
-
MDW
1 stop18h 25m
Delta
Deal found 1/11$560
This Delta deal was found by Cheapflights users on 1/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/86:00 am
MDW
-
SXM
1 stop6h 55m
Delta
Mon 2/161:38 pm
SXM
-
MDW
1 stop10h 53m
Delta
Deal found 1/12$579
This Gotogate deal was found by Cheapflights users on 1/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/216:00 am
MDW
-
SXM
1 stop7h 20m
Frontier
Sat 3/283:41 pm
SXM
-
MDW
1 stop29h 06m
Frontier
Deal found 1/11$581

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 January 12, 2026.
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

Fri 1/30

1:55 pm-10:22 pm

1 stop10h 27m

$509

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 2/8

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Tue 2/17

1:38 pm-10:33 pm

1 stop10h 55m

$509

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 2/18

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Wed 2/25

1:38 pm-10:31 pm

1 stop10h 53m

$509

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 2/11

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Tue 2/17

1:38 pm-10:33 pm

1 stop10h 55m

$509

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 2/10

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Tue 2/17

1:38 pm-10:33 pm

1 stop10h 55m

$509

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 2/11

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Wed 2/18

4:15 pm-12:46 pm

2 stops22h 31m

$514

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 2/9

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sat 2/14

1:38 pm-10:31 pm

1 stop10h 53m

$539

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 4/11

6:00 am-2:40 pm

1 stop7h 40m

$95

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 4/10

8:00 am-2:40 pm

2 stops29h 40m

$140

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 3/23

10:00 am-1:08 pm

2 stops26h 08m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/12

Showing 1-10 of 16 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 January 12, 2026.
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
8,039 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Entertainment

7.8

Food

7.2

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
8,039 reviews
Delta
7.9
Good
8,039 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Entertainment

7.8

Food

7.2

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 January 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$512Average$637FlexibilityNo cancel feeOn-timeN/A

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