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

$273+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$632
(Delta)

One-way from

$273
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$670
Provider with most accurate pricing for Chicago (CHI)-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Simpson Bay Princess Juliana flights.
Search Deals
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. 5% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 20, 2025.

This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/309:12 pmMDW - SXM
1 stop12h 46mFrontier
Sat 6/1412:18 pmSXM - MDW
2 stops12h 37mFrontier
Deal found 2/20$474
This Delta deal was found by Cheapflights users on 2/20. 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 4/96:00 amMDW - SXM
1 stop6h 59mDelta
Tue 4/151:46 pmSXM - MDW
1 stop9h 40mDelta
Deal found 2/20$632
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1912:55 pmMDW - SXM
1 stop24h 21mMultiple Airlines
Sat 4/2612:25 pmSXM - MDW
1 stop22h 55mMultiple Airlines
Deal found 2/19$646
This Kissandfly.com deal was found by Cheapflights users on 2/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/66:00 amMDW - SXM
1 stop6h 59mKLM
Sun 4/131:40 pmSXM - MDW
1 stop9h 41mKLM
Deal found 2/19$1,393
This SmartFares deal was found by Cheapflights users on 2/19. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/210:25 amMDW - SXM
2 stops26h 51mWestJet
Mon 4/143:10 pmSXM - MDW
2 stops24h 12mWestJet
Deal found 2/19$3,164

Find flights from Midway to Saint Martin Island within your budget

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 February 20, 2025.

Fly from

Midway

Fly to

Saint Martin Island

Route

Depart

Return

Price

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 4/9

6:00 am-1:59 pm

1 stop6h 59m

Simpson Bay Princess Juliana

Tue 4/15

1:46 pm-10:26 pm

1 stop9h 40m

$632

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 4/19

12:55 pm-2:16 pm

1 stop24h 21m

Simpson Bay Princess Juliana

Sat 4/26

12:25 pm-10:20 am

1 stop22h 55m

$646

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 4/6

6:00 am-1:59 pm

1 stop6h 59m

Simpson Bay Princess Juliana

Sun 4/13

1:40 pm-10:21 pm

1 stop9h 41m

$1,393

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 4/2

10:25 am-2:16 pm

2 stops26h 51m

Simpson Bay Princess Juliana

Mon 4/14

3:10 pm-2:22 pm

2 stops24h 12m

$3,164

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 3/2

12:43 pm-2:30 pm

2 stops23h 47m

$273

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 3/2

6:00 am-3:16 pm

1 stop7h 16m

$448

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 3/23

7:09 pm-2:16 pm

2 stops42h 07m

$1,596

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

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.

Travel insights for flights from Midway to Saint Martin Island

Get recent, data-driven insights about flights from Midway to Saint Martin Island including ideal travel times, pricing trends, and more.
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 February 20, 2025.
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

8.0

Boarding

8.2

Overall

8.0

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
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

8.0

Boarding

8.2

Overall

8.0

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.

KLM
7.8
Good
1,333 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

8.0

Boarding

8.2

Overall

8.0

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.

WestJet
7.2
Good
2,801 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

8.0

Boarding

8.2

Overall

8.0

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 $684). 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
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
Midway to Punta Cana flights
Midway to Montego Bay flights
O'Hare Intl to George Town flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Santo Domingo flights
Midway to Saint Thomas Island flights
O'Hare Intl to Castries flights
Midway to Nassau flights
O'Hare Intl to Puerto Plata flights
Midway to Oranjestad flights
O'Hare Intl to Christiansted flights
Midway to Simpson Bay flights
Midway to Providenciales flights
O'Hare Intl to Bridgetown flights
Midway to Santo Domingo flights
O'Hare Intl to St. John's flights
O'Hare Intl to Kingston flights
Midway to George Town flights
O'Hare Intl to Basseterre flights
O'Hare Intl to Santiago de los Caballeros flights
Midway to Castries flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to St. George's flights
O'Hare Intl to Freeport flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Georgetown flights
O'Hare Intl to The Valley flights
O'Hare Intl to Castries flights
O'Hare Intl to Havana flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Road Town flights
Midway to Kingston 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 Kingstown flights
O'Hare Intl to Pointe-à-Pitre flights
Midway to Gregory Town flights
Midway to Georgetown flights
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.