$189+ 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Oct 8 — Oct 151
Round-trip
1 adult, Economy
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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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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 September 8, 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 September 8, 2026.
This Southwest deal was found by Cheapflights users on 9/3. 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 11/65:10 am -
1 stop8h 30m
Fri 11/134:40 pm -
1 stop8h 25m
Deal found 9/3![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 9/4. 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 10/297:15 pm -
2 stops17h 50m
Sun 11/14:40 pm -
1 stop8h 25m
Deal found 9/4![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 9/7. 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 10/226:25 pm -
2 stops18h 40m
Thu 10/293:05 pm -
2 stops9h 50m
Deal found 9/7![Southwest logo]()
$499
This Southwest deal was found by Cheapflights users on 9/3. 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 10/19:20 pm -
2 stops15h 45m
Thu 10/83:05 pm -
1 stop10h 20m
Deal found 9/3![Southwest logo]()
$516
This Southwest deal was found by Cheapflights users on 9/3. 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 12/303:15 pm -
2 stops21h 05m
Wed 1/63:35 pm -
2 stops16h 05m
Deal found 9/3![Southwest logo]()
$538
This Southwest deal was found by Cheapflights users on 9/3. 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 11/55:05 am -
1 stop7h 15m
Thu 11/54:40 pm -
1 stop8h 25m
Deal found 9/3![Southwest logo]()
$543
This Southwest deal was found by Cheapflights users on 9/7. 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 11/228:25 pm -
2 stops17h 15m
Tue 12/13:20 pm -
2 stops16h 20m
Deal found 9/7![Southwest logo]()
$552
This Southwest deal was found by Cheapflights users on 9/4. 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 11/95:05 am -
1 stop7h 15m
Mon 11/163:20 pm -
2 stops16h 20m
Deal found 9/4![Southwest logo]()
$571
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 September 8, 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 September 8, 2026.
This Southwest deal was found by Cheapflights users on 9/7. 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 12/38:50 pm -
2 stops15h 30m
Thu 12/103:20 pm -
2 stops22h 30m
Deal found 9/7![Southwest logo]()
$584
This Delta deal was found by Cheapflights users on 9/2. 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 10/246:04 am -
1 stop6h 36m
Sat 10/313:05 pm -
1 stop8h 28m
Deal found 9/2![Delta logo]()
$665
This Southwest deal was found by Cheapflights users on 9/3. 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 10/98:55 pm -
2 stops15h 50m
Mon 10/123:05 pm -
2 stops18h 10m
Deal found 9/3![Southwest logo]()
$590
This Southwest deal was found by Cheapflights users on 9/4. 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 10/25:00 am -
1 stop8h 05m
Mon 10/123:05 pm -
1 stop10h 20m
Deal found 9/4![Southwest logo]()
$591
This Delta deal was found by Cheapflights users on 9/3. 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 9/186:05 am -
1 stop6h 48m
Fri 9/253:18 pm -
1 stop8h 26m
Deal found 9/3![Delta logo]()
$675
This Southwest deal was found by Cheapflights users on 9/5. 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 stop7h 00m
Sun 12/63:15 pm -
2 stops19h 45m
Deal found 9/5![Southwest logo]()
$655
This Delta deal was found by Cheapflights users on 9/7. 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 9/7![Delta logo]()
$752
This Delta deal was found by Cheapflights users on 9/7. 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
Sat 12/123:36 pm -
1 stop9h 19m
Deal found 9/7![Delta logo]()
$768
Last-minute flights from Midway to St. MaartenDiscover last-minute flight deals from Midway to St. Maarten. Data last updated September 8, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to St. Maarten. Data last updated September 8, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/6. 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 9/205:10 am -
1 stop7h 55m
Thu 9/243:05 pm -
1 stop8h 40m
Deal found 9/6![Southwest logo]()
$595
This Southwest deal was found by Cheapflights users on 9/3. 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 10/19:20 pm -
2 stops15h 45m
Thu 10/83:05 pm -
1 stop10h 20m
Deal found 9/3![Southwest logo]()
$516
This Southwest deal was found by Cheapflights users on 9/4. 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 10/25:00 am -
1 stop8h 05m
Mon 10/123:05 pm -
2 stops18h 10m
Deal found 9/4![Southwest logo]()
$571
This Southwest deal was found by Cheapflights users on 9/3. 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 10/98:55 pm -
2 stops15h 50m
Mon 10/123:05 pm -
2 stops18h 10m
Deal found 9/3![Southwest logo]()
$590
This Southwest deal was found by Cheapflights users on 9/7. 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 10/226:25 pm -
2 stops18h 40m
Thu 10/293:05 pm -
2 stops9h 50m
Deal found 9/7![Southwest logo]()
$499
This Southwest deal was found by Cheapflights users on 9/4. 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 10/297:15 pm -
2 stops17h 50m
Sun 11/14:40 pm -
1 stop8h 25m
Deal found 9/4![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 9/5. 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 10/305:00 am -
1 stop8h 05m
Sun 11/83:20 pm -
1 stop9h 35m
Deal found 9/5![Southwest logo]()
$599
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 September 8, 2026.
Search for one-way flight options from Midway to St. Maarten. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.
This Southwest deal was found by Cheapflights users on 9/3. 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 11/65:10 am -
1 stop8h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 9/3. 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 11/58:25 pm -
2 stops17h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 9/4. 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 9/266:00 pm -
2 stops19h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 9/6. 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 11/288:55 pm -
2 stops17h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Southwest logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Sat 9/266:25 am -
3 stops28h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$272
This Delta deal was found by Cheapflights users on 9/7. 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 9/236:05 am -
1 stop6h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$282
This Delta deal was found by Cheapflights users on 9/7. 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 9/227:01 pm -
2 stops17h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 9/4. 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 9/245:00 am -
1 stop8h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Southwest logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 11/66:16 am -
3 stops27h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Multiple Airlines logo]()
$336
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 September 8, 2026.
Round-trip from | $467 (Southwest) |
|---|---|
One-way from | $189 (Southwest) |
Popular in | December |
Cheapest in | January |
Average price | $670 |
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 September 8, 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
Thu 11/5
8:25 pm-3:40 pm
2 stops17h 15m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$212
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Sat 9/26
6:00 pm-2:05 pm
2 stops19h 05m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$222
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Fri 11/6
8:25 pm-2:20 pm
2 stops15h 55m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$281
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Wed 9/23
6:05 am-1:53 pm
1 stop6h 48m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$282
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Tue 9/22
7:01 pm-1:53 pm
2 stops17h 52m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$288
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Thu 9/24
5:00 am-2:05 pm
1 stop8h 05m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$322
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Wed 9/23
8:20 pm-2:05 pm
2 stops16h 45m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$369
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
$383
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Thu 12/3
8:50 pm-2:20 pm
2 stops15h 30m
Simpson Bay Princess Juliana
Thu 12/10
3:20 pm-11:50 am
2 stops22h 30m
$584
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Fri 10/9
8:55 pm-1:45 pm
2 stops15h 50m
Simpson Bay Princess Juliana
Mon 10/12
3:05 pm-8:15 am
2 stops18h 10m
$590
Showing 1-10 of 16 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
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.
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