HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Saint Martin Island

$368+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
ago. 18 — ago. 251
lun. 8/18
lun. 8/25
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Saint Martin Island with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 agosto 13, 2025.

Round-trip from

$592
(Delta)

One-way from

$368
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$637
From Chicago Midway to Saint Martin Island
Search Deals
One-way flight from Chicago Midway to Saint Martin Island
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($81 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 agosto 13, 2025.

This Delta deal was found by Cheapflights users on 8/11. 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.
lun. 9/86:00 amMDW - SXM
1 stop6h 45mDelta
mié. 9/173:20 pmSXM - MDW
2 stops28h 15mDelta
Deal found 8/11$592
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/69:35 amMDW - SXM
1 stop26h 39mMultiple Airlines
sáb. 9/133:05 pmSXM - MDW
2 stops19h 18mMultiple Airlines
Deal found 8/11$599
This Delta deal was found by Cheapflights users on 8/11. 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.
sáb. 9/136:00 amMDW - SXM
1 stop6h 50mDelta
mié. 9/173:20 pmSXM - MDW
2 stops28h 15mDelta
Deal found 8/11$617
This Delta deal was found by Cheapflights users on 8/10. 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.
vie. 11/286:00 amMDW - SXM
1 stop6h 35mDelta
sáb. 12/64:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 8/10$767
This Delta deal was found by Cheapflights users on 8/13. 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.
jue. 12/116:00 amMDW - SXM
1 stop6h 35mDelta
mar. 12/164:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 8/13$782
This Delta deal was found by Cheapflights users on 8/11. 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.
mié. 11/56:00 amMDW - SXM
1 stop6h 49mDelta
mar. 11/114:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 8/11$847
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
sáb. 12/1311:00 amMDW - SXM
1 stop26h 21mMultiple Airlines
lun. 12/224:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Deal found 8/13$861
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
sáb. 12/1311:00 amMDW - SXM
1 stop26h 21mMultiple Airlines
dom. 12/214:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Deal found 8/13$888
This Delta deal was found by Cheapflights users on 8/12. 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.
sáb. 10/186:00 amMDW - SXM
1 stop6h 49mDelta
sáb. 10/253:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 8/12$897
This Delta deal was found by Cheapflights users on 8/11. 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.
sáb. 9/66:00 amMDW - SXM
1 stop6h 56mDelta
sáb. 9/133:20 pmSXM - MDW
1 stop19h 20mDelta
Deal found 8/11$913
This Delta deal was found by Cheapflights users on 8/11. 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.
mar. 10/146:23 pmMDW - SXM
2 stops18h 26mDelta
dom. 10/193:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 8/11$962

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 agosto 13, 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

mar. 9/9

9:30 am-1:45 pm

2 stops27h 15m

Simpson Bay Princess Juliana

mié. 9/17

3:20 pm-12:28 pm

2 stops22h 08m

$592

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

mié. 9/10

6:00 am-1:45 pm

1 stop6h 45m

Simpson Bay Princess Juliana

vie. 9/19

3:20 pm-8:40 am

2 stops18h 20m

$592

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

lun. 9/8

6:00 am-1:45 pm

1 stop6h 45m

Simpson Bay Princess Juliana

mié. 9/17

3:20 pm-6:35 pm

2 stops28h 15m

$592

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

mar. 9/9

1:08 pm-1:45 pm

2 stops23h 37m

Simpson Bay Princess Juliana

vie. 9/19

3:20 pm-8:40 am

2 stops18h 20m

$592

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

lun. 9/8

6:00 am-1:45 pm

1 stop6h 45m

Simpson Bay Princess Juliana

vie. 9/19

3:20 pm-12:28 pm

2 stops22h 08m

$592

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

mié. 9/10

6:00 am-1:45 pm

1 stop6h 45m

Simpson Bay Princess Juliana

mié. 9/17

3:20 pm-6:35 pm

2 stops28h 15m

$592

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

sáb. 9/6

9:35 am-1:14 pm

1 stop26h 39m

Simpson Bay Princess Juliana

sáb. 9/13

3:05 pm-9:23 am

2 stops19h 18m

$599

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

sáb. 1/31

6:00 am-2:56 pm

1 stop6h 56m

Simpson Bay Princess Juliana

vie. 2/6

1:45 pm-9:46 pm

1 stop10h 01m

$612

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

dom. 2/1

6:00 am-2:56 pm

1 stop6h 56m

Simpson Bay Princess Juliana

dom. 2/8

1:45 pm-9:46 pm

1 stop10h 01m

$612

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

vie. 9/12

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

vie. 9/19

3:20 pm-8:40 am

2 stops18h 20m

$617

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 15 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 agosto 13, 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
7,979 reviews

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

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
7,979 reviews
Delta
8.0
Very good
7,979 reviews

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

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.

  • 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 $654). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Saint Martin Island

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
Midway to Punta Cana flights
Midway to Montego Bay flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Providenciales flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Castries flights
Midway to Oranjestad flights
O'Hare Intl to Willemstad flights
Midway to Saint Thomas Island flights
Midway to Nassau flights
Midway to Santo Domingo flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Christiansted flights
O'Hare Intl to St. John's flights
Midway to George Town flights
O'Hare Intl to Kingston flights
Midway to Providenciales flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Puerto Plata flights
Midway to Simpson Bay flights
O'Hare Intl to Ponce flights
Midway to Castries flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to St. George's flights
O'Hare Intl to Road Town flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Castries flights
Midway to Kingston flights
O'Hare Intl to Havana flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Basseterre flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Freeport flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Kingstown flights
Midway to St. John's flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Fort-de-France flights
Midway to Santiago de los Caballeros flights
O'Hare Intl to Port Au Prince flights

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 agosto 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$622Average$637FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.