HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
St. Maarten

$184+ Cheap flights from Midway (MDW) to St. Maarten

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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to St. Maarten 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.

Find flight deals from Midway to St. Maarten

Cheapest flights from Midway to St. Maarten
Explore the most affordable flight options available from Midway to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Delta deal was found by Cheapflights users on 11/1. 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 12/156:00 amMDW - SXM
1 stop6h 28mDelta
Wed 12/173:53 pmSXM - MDW
1 stop9h 54mDelta
Deal found 11/1$375
This Delta deal was found by Cheapflights users on 11/1. 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 12/116:00 amMDW - SXM
1 stop6h 28mDelta
Thu 12/181:45 pmSXM - MDW
1 stop12h 02mDelta
Deal found 11/1$463
This Delta deal was found by Cheapflights users on 11/1. 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.
Fri 11/76:00 amMDW - SXM
1 stop6h 49mDelta
Mon 11/104:20 pmSXM - MDW
1 stop9h 20mDelta
Deal found 11/1$717
This Delta deal was found by Cheapflights users on 11/2. 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.
Fri 12/197:02 pmMDW - SXM
1 stop17h 15mDelta
Fri 1/94:20 pmSXM - MDW
2 stops20h 14mDelta
Deal found 11/2$747
This Delta deal was found by Cheapflights users on 11/2. 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.
Fri 12/197:02 pmMDW - SXM
1 stop17h 15mDelta
Sat 1/103:42 pmSXM - MDW
1 stop19h 26mDelta
Deal found 11/2$767
This Delta deal was found by Cheapflights users on 11/1. 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.
Fri 11/146:00 amMDW - SXM
1 stop6h 55mDelta
Mon 11/174:20 pmSXM - MDW
1 stop9h 20mDelta
Deal found 11/1$812
This Mytrip deal was found by Cheapflights users on 11/1. 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.
Tue 12/169:59 amMDW - SXM
2 stops28h 01mMultiple Airlines
Tue 12/233:40 pmSXM - MDW
2 stops20h 25mMultiple Airlines
Deal found 11/1$853
This Delta deal was found by Cheapflights users on 11/2. 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 12/216:00 amMDW - SXM
1 stop6h 50mDelta
Fri 1/94:20 pmSXM - MDW
2 stops20h 14mDelta
Deal found 11/2$889
This Delta deal was found by Cheapflights users on 11/2. 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 12/206:08 pmMDW - SXM
2 stops18h 42mDelta
Fri 1/94:20 pmSXM - MDW
2 stops20h 14mDelta
Deal found 11/2$942

Cheap flight deals from Midway to St. Maarten

Keep the following information in mind while searching for Midway to St. Maarten flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$369
(Frontier)

One-way from

$184
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$682
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 St. Maarten
Search Deals
One-way flight from Chicago Midway to St. Maarten
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($63 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to St. Maarten 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 November 3, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to St. Maarten that are best for you.

Fly from

Midway

Fly to

St. Maarten

Route

Depart

Return

Price

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 1/24

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 1/31

4:30 pm-11:25 pm

1 stop8h 55m

$369

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 12/16

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Tue 12/23

1:45 pm-10:22 pm

1 stop10h 37m

$375

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/21

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/28

4:30 pm-11:25 pm

1 stop8h 55m

$393

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/14

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/28

4:30 pm-11:25 pm

1 stop8h 55m

$393

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 12/11

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Thu 12/18

1:45 pm-11:47 pm

1 stop12h 02m

$463

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 3/10

6:00 am-1:53 pm

1 stop6h 53m

Simpson Bay Princess Juliana

Wed 3/11

3:45 pm-12:01 pm

2 stops21h 16m

$672

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 3/11

6:00 am-1:53 pm

1 stop6h 53m

Simpson Bay Princess Juliana

Wed 3/18

12:45 pm-9:46 pm

1 stop10h 01m

$757

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 12/19

7:02 pm-2:17 pm

1 stop17h 15m

Simpson Bay Princess Juliana

Sat 1/10

3:42 pm-9:08 am

1 stop19h 26m

$767

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 1/24

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sun 2/1

1:55 pm-10:26 pm

1 stop10h 31m

$819

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 3/25

6:00 am-1:53 pm

1 stop6h 53m

Simpson Bay Princess Juliana

Thu 4/2

12:45 pm-9:46 pm

1 stop10h 01m

$847

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 19 results
1
2

Best time to book a flight from Midway to St. Maarten

Have a flexible travel schedule? Discover the best time to fly to St. Maarten 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 St. Maarten
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing St. Maarten

Get insights into the airlines that provide service to St. Maarten. 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 St. Maarten. Reviews last updated November 3, 2025.
Get a feel of what it's like to fly with Delta from Chicago Midway Airport to St. Maarten by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,001 reviews

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.
Delta
7.9
Good
8,001 reviews
Delta
7.9
Good
8,001 reviews

Overall

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Lane,Nov 2025

MEM - ATL

The crew was very friendly, but they only came around and offered the better Delta Comfort snacks one time. I thought they would come around more frequently on a 5 hour flight. They did do two beverage services though, which was nice.

Related info for your journey

Find useful and relevant information for your journey from Midway to St. Maarten. 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 St. Maarten?

    There are many flights that can get you from Chicago Midway Airport to St. Maarten in 6h 28m. Fly via Frontier or Delta to get the fastest option. The distance from Chicago Midway Airport to St. Maarten is about 2189 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Midway to St. Maarten that include hotel bookings?

    Yes. In addition to deals on Midway to St. Maarten flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to St. Maarten?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to St. Maarten.

  • Can I find deals for business class flights from Midway to St. Maarten?

    Yes. Cheapflights offers flight deals from Midway to St. Maarten 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

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 St. Maarten

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

Top airline flying from Midway to St. Maarten

Discover the top airline that operate flights from Midway to St. Maarten. 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 November 3, 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.