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Saint Martin Island

$406+ 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 12/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$444
(Priceline)

One-way from

$406
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$642
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. 8% potential increase in price ($67 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 September 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 September 29, 2025.

This Delta deal was found by Cheapflights users on 9/27. 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 10/276:00 amMDW - SXM
1 stop6h 49mDelta
Fri 10/313:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 9/27$687
This Delta deal was found by Cheapflights users on 9/27. 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 11/56:00 amMDW - SXM
1 stop6h 49mDelta
Tue 11/114:20 pmSXM - MDW
1 stop9h 20mDelta
Deal found 9/27$732
This Delta deal was found by Cheapflights users on 9/28. 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 11/126:00 amMDW - SXM
1 stop6h 55mDelta
Wed 11/194:20 pmSXM - MDW
1 stop9h 20mDelta
Deal found 9/28$737
This Delta deal was found by Cheapflights users on 9/27. 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.
Thu 11/136:00 amMDW - SXM
1 stop6h 55mDelta
Sun 11/164:20 pmSXM - MDW
1 stop9h 20mDelta
Deal found 9/27$742
This Mytrip deal was found by Cheapflights users on 9/29. 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 10/271:48 pmMDW - SXM
2 stops23h 33mWestJet
Fri 10/313:20 pmSXM - MDW
2 stops20h 10mWestJet
Deal found 9/29$757
This Delta deal was found by Cheapflights users on 9/29. 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.
Thu 11/66:00 amMDW - SXM
1 stop6h 49mDelta
Thu 11/134:20 pmSXM - MDW
1 stop9h 20mDelta
Deal found 9/29$762
This Mytrip deal was found by Cheapflights users on 9/28. 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 10/271:48 pmMDW - SXM
2 stops23h 33mMultiple Airlines
Fri 10/314:00 pmSXM - MDW
2 stops19h 30mMultiple Airlines
Deal found 9/28$780
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/104:12 pmMDW - SXM
2 stops20h 48mMultiple Airlines
Sun 10/122:10 pmSXM - MDW
1 stop19h 29mMultiple Airlines
Deal found 9/27$866
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 12/612:45 pmMDW - SXM
1 stop24h 36mMultiple Airlines
Sat 12/136:10 pmSXM - MDW
2 stops31h 15mMultiple Airlines
Deal found 9/27$884

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 September 29, 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

Mon 10/27

6:00 am-1:49 pm

1 stop6h 49m

Simpson Bay Princess Juliana

Fri 10/31

3:14 pm-10:14 pm

1 stop8h 00m

$687

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 11/12

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Wed 11/19

4:20 pm-11:40 pm

1 stop9h 20m

$737

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 11/26

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Tue 12/2

3:53 pm-11:49 pm

1 stop9h 56m

$737

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 11/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Tue 12/2

3:53 pm-11:49 pm

1 stop9h 56m

$737

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 11/13

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sun 11/16

4:20 pm-11:40 pm

1 stop9h 20m

$742

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 10/27

1:48 pm-2:21 pm

2 stops23h 33m

Simpson Bay Princess Juliana

Fri 10/31

3:20 pm-10:30 am

2 stops20h 10m

$757

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 11/6

6:00 am-2:49 pm

1 stop6h 49m

Simpson Bay Princess Juliana

Thu 11/13

4:20 pm-11:40 pm

1 stop9h 20m

$762

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 10/27

1:48 pm-2:21 pm

2 stops23h 33m

Simpson Bay Princess Juliana

Fri 10/31

4:00 pm-10:30 am

2 stops19h 30m

$780

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 12/6

1:50 pm-3:21 pm

2 stops23h 31m

Simpson Bay Princess Juliana

Sat 12/13

3:40 pm-10:05 am

2 stops20h 25m

$901

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 12/27

6:00 am-3:20 pm

1 stop7h 20m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/28

Showing 1-10 of 11 results
1
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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 September 29, 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
8.0
Very good
7,964 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

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
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

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 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 49m. 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Saint Martin Island?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Saint Martin Island (average of $459). Flying from Chicago Midway Airport to Saint Martin Island in March is currently the most expensive (average of $651). 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 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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$622Average$637FlexibilityNo cancel feeOn-timeN/A

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