$361+ Cheap flights from St. Maarten to Midway (MDW)
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 3/28. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Jan 20 — Jan 271
1 adult, Economy
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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 St. Maarten to Midway
Best flights from St. Maarten to MidwayDiscover carefully curated flight deals from St. Maarten to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 21, 2025.
Discover carefully curated flight deals from St. Maarten to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 21, 2025.
This Mytrip deal was found by Cheapflights users on 12/19. 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.
Mon 2/21:05 pmSXM - MDW
2 stops23h 00mMultiple Airlines
Mon 2/911:00 amMDW - SXM
3 stops25h 40mMultiple Airlines
Deal found 12/19![Multiple Airlines logo]()
$679
This Delta deal was found by Cheapflights users on 12/19. 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 2/21:55 pmSXM - MDW
1 stop10h 27mDelta
Mon 2/96:00 amMDW - SXM
1 stop6h 55mDelta
Deal found 12/19![Delta logo]()
$690
Find flight deals from St. Maarten to Midway
Keep the following information in mind while searching for St. Maarten to Midway flight deals. Data was last updated December 21, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $679 (Mytrip) |
One-way from | $361 (Priceline) |
Cheapflights Fare Finder
Customize your flight search to find flights from St. Maarten to Midway 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 December 21, 2025.
Use the filters below to find and compare flights from St. Maarten to Chicago Midway Airport that are best for you.
Fly from
St. Maarten
Fly to
Midway
Route
Depart
Return
Price
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Mon 2/2
1:05 pm-10:05 am
2 stops23h 00m
Chicago Midway
Mon 2/9
11:00 am-2:40 pm
3 stops25h 40m
$679
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Mon 2/2
1:55 pm-10:22 pm
1 stop10h 27m
Chicago Midway
Mon 2/9
6:00 am-2:55 pm
1 stop6h 55m
$690
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Sat 3/28
3:41 pm-7:47 pm
1 stop29h 06m
$361
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Thu 3/26
11:30 am-5:48 pm
2 stops31h 18m
$393
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Fri 3/27
3:20 pm-11:50 am
1 stop21h 30m
$435
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Fri 3/27
3:20 pm-1:23 pm
2 stops23h 03m
$447
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Thu 3/26
12:55 pm-10:29 pm
1 stop10h 34m
$460
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Sat 3/28
2:15 pm-7:47 pm
2 stops30h 32m
$512
Best time to book a flight from St. Maarten to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from St. Maarten with our price prediction graph.
Estimated round-trip price
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Cheapflights Insights
Everything you need to know about your flight from St. Maarten to Chicago Midway Airport
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Related info for your journey
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