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Saint Martin Island

$411+ Cheap flights from Midway (MDW) to Saint Martin Island

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
mai 6 — mai 131
mar. 5/6
mar. 5/13
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 mai 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$411
(Frontier)

Popular in

March

Cheapest in

September

Average price

$714
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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Highest demand for flights based on searches. 4% potential increase in price ($31 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 May 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 mai 1, 2025.

This Frontier deal was found by Cheapflights users on 4/30. 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.
ven. 5/309:12 pmMDW - SXM
1 stop13h 12mFrontier
sam. 6/1412:36 pmSXM - MDW
1 stop8h 41mFrontier
Deal found 4/30$411
This Delta deal was found by Cheapflights users on 4/30. 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.
jeu. 12/46:00 amMDW - SXM
1 stop6h 35mDelta
sam. 12/134:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 4/30$1,037
This Mytrip deal was found by Cheapflights users on 4/30. 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.
lun. 6/29:20 amMDW - SXM
2 stops26h 40mMultiple Airlines
lun. 6/93:40 pmSXM - MDW
3 stops27h 00mMultiple Airlines
Deal found 4/30$3,494
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/295:04 pmMDW - SXM
2 stops20h 13mWestJet
dim. 1/44:10 pmSXM - MDW
2 stops21h 08mWestJet
Deal found 4/30$4,195

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 mai 1, 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

ven. 5/30

9:12 pm-11:24 am

1 stop13h 12m

Simpson Bay Princess Juliana

sam. 6/14

12:36 pm-8:17 pm

1 stop8h 41m

$411

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

lun. 6/2

9:20 am-1:00 pm

2 stops26h 40m

Simpson Bay Princess Juliana

lun. 6/9

3:40 pm-5:40 pm

3 stops27h 00m

$3,494

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

sam. 6/14

6:00 am-2:00 pm

1 stop7h 00m

$518

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 mai 1, 2025.
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Frontier
6.0
Okay
3,287 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

  • 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 July is currently the most expensive (average of $669). 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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