$252+ Cheap flights from Midway (MDW) to St. Maarten
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 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Nov 21 — Nov 281
Round-trip
1 adult, Economy
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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
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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 St. Maarten
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One-way
Cheapest flights from Midway to St. MaartenExplore 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 October 22, 2026.
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 October 22, 2026.
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/145:20 am -
1 stop6h 55m
Fri 12/183:15 pm -
1 stop10h 00m
Deal found 10/19![Southwest logo]()
$547
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:20 am -
1 stop6h 55m
Fri 12/114:40 pm -
1 stop8h 30m
Deal found 10/19![Southwest logo]()
$576
This Southwest deal was found by Cheapflights users on 10/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/289:05 pm -
2 stops16h 35m
Fri 1/83:35 pm -
1 stop9h 15m
Deal found 10/17![Southwest logo]()
$593
This Delta deal was found by Cheapflights users on 10/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/216:00 am -
1 stop6h 45m
Tue 12/291:40 pm -
1 stop10h 42m
Deal found 10/19![Delta logo]()
$629
This Delta deal was found by Cheapflights users on 10/18. 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 12/209:30 am -
2 stops27h 15m
Wed 12/301:40 pm -
2 stops21h 10m
Deal found 10/18![Delta logo]()
$634
This Southwest deal was found by Cheapflights users on 10/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/165:20 am -
1 stop6h 55m
Sun 12/204:40 pm -
2 stops17h 40m
Deal found 10/18![Southwest logo]()
$639
This Southwest deal was found by Cheapflights users on 10/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/315:20 am -
1 stop6h 55m
Thu 1/73:35 pm -
1 stop9h 15m
Deal found 10/17![Southwest logo]()
$642
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:00 am -
1 stop7h 15m
Sat 11/213:15 pm -
1 stop9h 50m
Deal found 10/21![Southwest logo]()
$644
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/115:20 am -
1 stop6h 55m
Sat 11/143:15 pm -
1 stop8h 30m
Deal found 10/21![Southwest logo]()
$648
This Delta deal was found by Cheapflights users on 10/21. 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 12/56:00 am -
1 stop6h 45m
Fri 12/114:05 pm -
1 stop8h 49m
Deal found 10/21![Delta logo]()
$649
Best flights from Midway to St. MaartenDiscover carefully curated flight deals from Midway to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 22, 2026.
Discover carefully curated flight deals from Midway to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 22, 2026.
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/255:10 am -
1 stop8h 05m
Wed 3/33:35 pm -
1 stop9h 15m
Deal found 10/20![Southwest logo]()
$584
This Delta deal was found by Cheapflights users on 10/18. 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.
Tue 12/226:00 am -
1 stop6h 45m
Mon 12/281:40 pm -
2 stops21h 10m
Deal found 10/18![Delta logo]()
$654
This Southwest deal was found by Cheapflights users on 10/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/289:05 pm -
2 stops16h 35m
Fri 1/83:35 pm -
1 stop9h 15m
Deal found 10/17![Southwest logo]()
$593
This Delta deal was found by Cheapflights users on 10/18. 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 12/209:30 am -
2 stops27h 15m
Mon 12/281:40 pm -
2 stops21h 10m
Deal found 10/18![Delta logo]()
$654
This Southwest deal was found by Cheapflights users on 10/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/165:20 am -
1 stop6h 55m
Sun 12/204:40 pm -
2 stops17h 40m
Deal found 10/18![Southwest logo]()
$639
This Delta deal was found by Cheapflights users on 10/18. 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 11/86:04 am -
1 stop6h 36m
Fri 11/134:05 pm -
1 stop8h 49m
Deal found 10/18![Delta logo]()
$685
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:00 am -
1 stop7h 15m
Sat 11/213:15 pm -
2 stops11h 10m
Deal found 10/21![Southwest logo]()
$649
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/175:05 am -
1 stop7h 10m
Mon 12/214:40 pm -
2 stops17h 40m
Deal found 10/21![Southwest logo]()
$682
This Southwest deal was found by Cheapflights users on 10/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:00 am -
1 stop7h 15m
Sat 12/193:15 pm -
1 stop8h 15m
Deal found 10/17![Southwest logo]()
$687
This Southwest deal was found by Cheapflights users on 10/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/285:45 am -
1 stop6h 50m
Mon 2/83:35 pm -
1 stop9h 20m
Deal found 10/17![Southwest logo]()
$695
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/165:25 am -
1 stop7h 05m
Sun 4/181:40 pm -
1 stop11h 00m
Deal found 10/20![Southwest logo]()
$695
This Southwest deal was found by Cheapflights users on 10/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/265:10 pm -
2 stops18h 20m
Sun 3/72:55 pm -
2 stops19h 35m
Deal found 10/20![Southwest logo]()
$699
Last-minute flights from Midway to St. MaartenDiscover last-minute flight deals from Midway to St. Maarten. Data last updated October 22, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to St. Maarten. Data last updated October 22, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/284:35 pm -
2 stops20h 30m
Wed 11/43:15 pm -
2 stops16h 25m
Deal found 10/21![Southwest logo]()
$690
This Southwest deal was found by Cheapflights users on 10/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:10 am -
1 stop8h 30m
Mon 11/93:15 pm -
1 stop9h 45m
Deal found 10/17![Southwest logo]()
$687
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:05 am -
1 stop7h 10m
Mon 11/94:40 pm -
1 stop8h 35m
Deal found 10/21![Southwest logo]()
$752
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:00 am -
1 stop7h 15m
Wed 11/113:15 pm -
2 stops16h 25m
Deal found 10/21![Southwest logo]()
$728
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:10 am -
1 stop8h 30m
Wed 11/113:15 pm -
2 stops16h 25m
Deal found 10/21![Southwest logo]()
$662
This Delta deal was found by Cheapflights users on 10/20. 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.
Sun 11/86:04 am -
1 stop6h 36m
Fri 11/134:05 pm -
1 stop8h 49m
Deal found 10/20![Delta logo]()
$685
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/115:20 am -
1 stop6h 55m
Sat 11/143:15 pm -
1 stop8h 30m
Deal found 10/21![Southwest logo]()
$648
This Delta deal was found by Cheapflights users on 10/21. 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 11/136:00 am -
1 stop6h 40m
Tue 11/174:05 pm -
1 stop8h 49m
Deal found 10/21![Delta logo]()
$740
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:00 am -
1 stop7h 15m
Sat 11/213:15 pm -
1 stop9h 50m
Deal found 10/21![Southwest logo]()
$644
This Delta deal was found by Cheapflights users on 10/21. 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.
Tue 11/176:00 am -
1 stop6h 40m
Sat 11/213:36 pm -
1 stop9h 18m
Deal found 10/21![Delta logo]()
$735
One-way flights from Midway to St. MaartenSearch for one-way flight options from Midway to St. Maarten. Find affordable one-way fares based on user searches. Data last updated October 22, 2026.
Search for one-way flight options from Midway to St. Maarten. Find affordable one-way fares based on user searches. Data last updated October 22, 2026.
This Southwest deal was found by Cheapflights users on 10/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/299:05 pm -
2 stops16h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 10/20. 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.
Sun 11/296:00 am -
1 stop6h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Delta logo]()
$298
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/239:05 pm -
2 stops15h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/279:05 pm -
2 stops16h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 1/158:47 pm -
3 stops35h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$442
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Wed 12/308:35 pm -
2 stops14h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Multiple Airlines logo]()
$464
This Southwest deal was found by Cheapflights users on 10/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/155:00 am -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Southwest logo]()
$479
Find 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 October 22, 2026.
Round-trip from | $547 (Southwest) |
|---|---|
One-way from | $252 (Southwest) |
Popular in | June |
Cheapest in | January |
Average price | $665 |
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 7,457,451 searches. Data last updated October 22, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to St. Maarten that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Tue 12/29
9:05 pm-3:40 pm
2 stops16h 35m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$252
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Wed 12/30
6:00 am-2:45 pm
1 stop6h 45m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$298
Quickest round-trip
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Sun 11/29
6:00 am-2:37 pm
1 stop6h 37m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$298
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Wed 12/23
9:05 pm-2:15 pm
2 stops15h 10m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$304
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Sun 12/27
9:05 pm-3:40 pm
2 stops16h 35m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$354
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Fri 1/15
8:47 pm-3:25 pm
2 stops40h 38m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$478
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Sat 12/26
8:55 pm-3:40 pm
2 stops16h 45m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$485
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Thu 2/25
5:10 am-3:15 pm
1 stop8h 05m
Simpson Bay Princess Juliana
Wed 3/3
3:35 pm-10:50 pm
1 stop9h 15m
$584
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Mon 12/28
9:05 pm-3:40 pm
2 stops16h 35m
Simpson Bay Princess Juliana
Fri 1/8
3:35 pm-10:50 pm
1 stop9h 15m
$593
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Wed 12/16
5:20 am-2:15 pm
1 stop6h 55m
Simpson Bay Princess Juliana
Sun 12/20
4:40 pm-8:20 am
2 stops17h 40m
$639
Showing 1-10 of 19 resultsSorted by cheapest first
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.
MDW-SXM
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
MDW-SX0
MDW-SXM
No data available for this route at this time. Please check back soon.
Related info for your journey
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