$115+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Mar 10 — Mar 171
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
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 St. Maarten
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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 February 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 February 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/911:00 am
MDW
- SXM
1 stop23h 15m
Multiple Airlines
Sat 3/142:20 pm
SXM
- MDW
2 stops32h 59m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$536
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
MDW
- SXM
1 stop6h 50m
Delta
Wed 3/1812:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/5![Delta logo]()
$571
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
MDW
- SXM
1 stop8h 00m
Delta
Sat 2/281:38 pm
SXM
- MDW
1 stop10h 53m
Delta
Deal found 2/5![Delta logo]()
$585
This Delta deal was found by Cheapflights users on 2/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:00 am
MDW
- SXM
1 stop6h 54m
Delta
Mon 3/1612:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/6![Delta logo]()
$598
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:00 am
MDW
- SXM
1 stop6h 54m
Delta
Tue 3/3112:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/5![Delta logo]()
$611
This Southwest deal was found by Cheapflights users on 2/4. 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 4/245:35 am
MDW
- SXM
1 stop7h 05m
Southwest
Tue 4/282:35 pm
SXM
- MDW
2 stops18h 00m
Southwest
Deal found 2/4![Southwest logo]()
$613
This Southwest deal was found by Cheapflights users on 2/6. 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.
Wed 6/38:50 pm
MDW
- SXM
2 stops16h 10m
Southwest
Sun 6/72:15 pm
SXM
- MDW
2 stops17h 55m
Southwest
Deal found 2/6![Southwest logo]()
$630
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:00 am
MDW
- SXM
1 stop6h 54m
Delta
Mon 3/1612:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/5![Delta logo]()
$631
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 February 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 February 8, 2026.
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
MDW
- SXM
1 stop6h 50m
Delta
Wed 3/1812:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/5![Delta logo]()
$571
This Southwest deal was found by Cheapflights users on 2/4. 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 4/245:35 am
MDW
- SXM
1 stop7h 05m
Southwest
Tue 4/282:35 pm
SXM
- MDW
2 stops18h 00m
Southwest
Deal found 2/4![Southwest logo]()
$613
This Delta deal was found by Cheapflights users on 2/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:00 am
MDW
- SXM
1 stop6h 54m
Delta
Mon 3/1612:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/6![Delta logo]()
$598
This Southwest deal was found by Cheapflights users on 2/6. 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.
Fri 4/245:35 am
MDW
- SXM
1 stop7h 05m
Southwest
Mon 4/272:35 pm
SXM
- MDW
1 stop10h 05m
Southwest
Deal found 2/6![Southwest logo]()
$645
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2412:47 pm
MDW
- SXM
2 stops21h 42m
Delta
Tue 3/313:20 pm
SXM
- MDW
2 stops28h 20m
Delta
Deal found 2/5![Delta logo]()
$616
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:00 am
MDW
- SXM
1 stop6h 54m
Delta
Mon 3/1612:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/5![Delta logo]()
$631
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:00 am
MDW
- SXM
1 stop6h 50m
Delta
Tue 3/31:38 pm
SXM
- MDW
1 stop10h 55m
Delta
Deal found 2/5![Delta logo]()
$635
This Delta deal was found by Cheapflights users on 2/7. 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.
Mon 3/96:00 am
MDW
- SXM
1 stop6h 54m
Delta
Mon 3/1612:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/7![Delta logo]()
$640
This Delta deal was found by Cheapflights users on 2/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:00 am
MDW
- SXM
1 stop6h 50m
Delta
Mon 3/912:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/6![Delta logo]()
$681
Last-minute flights from Midway to St. MaartenDiscover last-minute flight deals from Midway to St. Maarten. Data last updated February 8, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to St. Maarten. Data last updated February 8, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:00 am
MDW
- SXM
1 stop8h 00m
Delta
Sat 2/281:38 pm
SXM
- MDW
1 stop10h 53m
Delta
Deal found 2/5![Delta logo]()
$585
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:00 am
MDW
- SXM
1 stop6h 50m
Delta
Tue 3/31:38 pm
SXM
- MDW
1 stop10h 55m
Delta
Deal found 2/5![Delta logo]()
$635
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
MDW
- SXM
1 stop6h 50m
Delta
Wed 3/1812:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/5![Delta logo]()
$571
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/911:00 am
MDW
- SXM
1 stop23h 15m
Multiple Airlines
Sat 3/142:20 pm
SXM
- MDW
2 stops32h 59m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$536
This Delta deal was found by Cheapflights users on 2/7. 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.
Mon 3/96:00 am
MDW
- SXM
1 stop6h 54m
Delta
Mon 3/1612:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/7![Delta logo]()
$640
This Delta deal was found by Cheapflights users on 2/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:00 am
MDW
- SXM
1 stop6h 54m
Delta
Mon 3/1612:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/6![Delta logo]()
$598
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:00 am
MDW
- SXM
1 stop6h 54m
Delta
Mon 3/1612:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/5![Delta logo]()
$631
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:00 am
MDW
- SXM
1 stop6h 54m
Delta
Tue 3/3112:55 pm
SXM
- MDW
1 stop10h 36m
Delta
Deal found 2/5![Delta logo]()
$611
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 February 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 February 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/22:19 pm
MDW
- SXM
2 stops21h 56m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/289:15 am
MDW
- SXM
2 stops27h 00m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/122:41 pm
MDW
- SXM
2 stops21h 34m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/146:55 am
MDW
- SXM
2 stops29h 20m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$174
This Priceline deal was found by Cheapflights users on 2/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/132:41 pm
MDW
- SXM
1 stop21h 49m
Frontier
Deal found 2/7![Frontier logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:05 am
MDW
- SXM
2 stops30h 10m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$248
This Delta deal was found by Cheapflights users on 2/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/26:00 am
MDW
- SXM
1 stop6h 54m
Delta
Deal found 2/5![Delta logo]()
$308
This Delta deal was found by Cheapflights users on 2/7. 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.
Mon 3/26:00 am
MDW
- SXM
1 stop6h 50m
Delta
Deal found 2/7![Delta logo]()
$328
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 February 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $536 (Kiwi.com) |
One-way from | $115 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $600 |
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 February 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
Midway
Fly to
St. Maarten
Route
Depart
Return
Price
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Tue 3/3
6:00 am-2:50 pm
1 stop6h 50m
Simpson Bay Princess Juliana
Wed 3/18
12:55 pm-10:31 pm
1 stop10h 36m
$571
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Wed 3/11
6:00 am-1:54 pm
1 stop6h 54m
Simpson Bay Princess Juliana
Mon 3/16
12:55 pm-10:31 pm
1 stop10h 36m
$598
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 4/24
5:35 am-1:40 pm
1 stop7h 05m
Simpson Bay Princess Juliana
Tue 4/28
2:35 pm-7:35 am
2 stops18h 00m
$613
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Tue 3/24
12:47 pm-11:29 am
2 stops21h 42m
Simpson Bay Princess Juliana
Tue 3/31
3:20 pm-6:40 pm
2 stops28h 20m
$616
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Thu 3/12
6:00 am-1:54 pm
1 stop6h 54m
Simpson Bay Princess Juliana
Mon 3/16
12:55 pm-10:31 pm
1 stop10h 36m
$631
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Tue 2/24
6:00 am-2:50 pm
1 stop6h 50m
Simpson Bay Princess Juliana
Tue 3/3
1:38 pm-10:33 pm
1 stop10h 55m
$635
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Mon 3/9
6:00 am-1:54 pm
1 stop6h 54m
Simpson Bay Princess Juliana
Mon 3/16
12:55 pm-10:31 pm
1 stop10h 36m
$640
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 4/24
5:35 am-1:40 pm
1 stop7h 05m
Simpson Bay Princess Juliana
Mon 4/27
2:35 pm-11:40 pm
1 stop10h 05m
$645
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Wed 3/4
6:00 am-2:50 pm
1 stop6h 50m
Simpson Bay Princess Juliana
Mon 3/9
12:55 pm-10:31 pm
1 stop10h 36m
$681
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Mon 3/2
2:19 pm-2:15 pm
2 stops21h 56m
$115
Showing 1-10 of 17 results
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.
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 February 8, 2026.
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.
Food
7.2
Boarding
8.1
Overall
7.9
Entertainment
7.8
Crew
8.5
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Boarding
8.1
Overall
7.9
Entertainment
7.8
Crew
8.5
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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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Complete your trip
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Midway and St. Maarten flights
Browse other Midway and St. Maarten flight options. Last updated on February 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 February 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$512 | Average$637 | FlexibilityNo cancel fee | On-timeN/A |