$137+ Cheap flights from Chicago (CHI) 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Oct 3 — Oct 101
Round-trip
1 adult, Economy
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Find cheap flights from Chicago 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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Cheapest flights from Chicago to St. MaartenExplore the most affordable flight options available from Chicago to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 3, 2026.
Explore the most affordable flight options available from Chicago to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 3, 2026.
This Flightnetwork deal was found by Cheapflights users on 9/1. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:40 pm -
1 stop19h 20m
Sun 11/14:45 pm -
1 stop18h 38m
Deal found 9/1![Air Canada logo]()
$388
This Air Canada deal was found by Cheapflights users on 8/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:40 pm -
1 stop17h 05m
Sat 10/312:40 pm -
1 stop26h 12m
Deal found 8/30![Air Canada logo]()
$404
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:45 am -
1 stop29h 00m
Sun 11/84:45 pm -
1 stop29h 13m
Deal found 9/3![Air Canada logo]()
$405
This Air Canada deal was found by Cheapflights users on 8/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2510:57 am -
2 stops26h 48m
Sat 10/312:40 pm -
1 stop26h 12m
Deal found 8/31![Air Canada logo]()
$409
This Justfly.com deal was found by Cheapflights users on 9/1. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:40 pm -
1 stop17h 05m
Fri 11/64:45 pm -
1 stop22h 28m
Deal found 9/1![Air Canada logo]()
$411
This Expedia deal was found by Cheapflights users on 8/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:45 am -
2 stops31h 15m
Mon 10/263:45 pm -
1 stop29h 28m
Deal found 8/29![Air Canada logo]()
$412
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/812:50 pm -
1 stop24h 55m
Fri 11/134:45 pm -
1 stop26h 58m
Deal found 9/2![Air Canada logo]()
$413
This Air Canada deal was found by Cheapflights users on 8/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:09 am -
1 stop8h 51m
Mon 10/263:45 pm -
1 stop18h 38m
Deal found 8/31![Air Canada logo]()
$414
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:00 am -
1 stop6h 40m
Fri 11/134:40 pm -
1 stop8h 25m
Deal found 9/2![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 9/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/164:10 pm -
2 stops20h 10m
Mon 11/234:40 pm -
2 stops19h 15m
Deal found 9/1![Southwest logo]()
$489
This Southwest deal was found by Cheapflights users on 9/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:05 am -
1 stop7h 10m
Thu 12/33:20 pm -
2 stops16h 20m
Deal found 9/1![Southwest logo]()
$506
This Southwest deal was found by Cheapflights users on 8/29. 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 10/35:00 am -
1 stop7h 45m
Sat 10/102:45 pm -
2 stops17h 40m
Deal found 8/29![Southwest logo]()
$525
Best flights from Chicago to St. MaartenDiscover carefully curated flight deals from Chicago to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 3, 2026.
Discover carefully curated flight deals from Chicago to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 3, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:25 pm -
2 stops17h 15m
Fri 11/134:40 pm -
1 stop8h 25m
Deal found 9/2![Southwest logo]()
$472
This United Airlines deal was found by Cheapflights users on 8/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/208:45 am -
Nonstop5h 12m
Fri 2/262:52 pm -
1 stop18h 39m
Deal found 8/30![United Airlines logo]()
$654
This Southwest deal was found by Cheapflights users on 8/31. 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 11/274:00 pm -
2 stops19h 30m
Thu 12/33:20 pm -
2 stops22h 45m
Deal found 8/31![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 9/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/245:45 am -
1 stop6h 50m
Sun 2/284:15 pm -
1 stop8h 50m
Deal found 9/1![Southwest logo]()
$527
This Southwest deal was found by Cheapflights users on 9/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/175:10 am -
1 stop8h 30m
Mon 12/214:40 pm -
2 stops20h 05m
Deal found 9/1![Southwest logo]()
$542
This United Airlines deal was found by Cheapflights users on 9/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/68:40 am -
Nonstop5h 17m
Sat 2/132:40 pm -
Nonstop6h 00m
Deal found 9/1![United Airlines logo]()
$658
This United Airlines deal was found by Cheapflights users on 9/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/208:45 am -
Nonstop5h 12m
Sat 2/272:40 pm -
Nonstop6h 00m
Deal found 9/1![United Airlines logo]()
$658
This Southwest deal was found by Cheapflights users on 9/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:20 am -
1 stop7h 00m
Sun 12/64:40 pm -
1 stop8h 25m
Deal found 9/1![Southwest logo]()
$544
This United Airlines deal was found by Cheapflights users on 9/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/245:55 am -
1 stop7h 53m
Sun 2/284:55 pm -
1 stop8h 20m
Deal found 9/1![United Airlines logo]()
$658
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:10 pm -
2 stops17h 55m
Sat 10/242:45 pm -
2 stops17h 40m
Deal found 9/2![Southwest logo]()
$545
This United Airlines deal was found by Cheapflights users on 8/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/98:40 am -
Nonstop5h 17m
Sat 1/235:00 pm -
1 stop8h 59m
Deal found 8/31![United Airlines logo]()
$668
This Southwest deal was found by Cheapflights users on 8/29. 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 9/265:00 am -
1 stop6h 55m
Sat 10/32:45 pm -
2 stops17h 40m
Deal found 8/29![Southwest logo]()
$578
This Southwest deal was found by Cheapflights users on 8/30. 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 -
1 stop10h 20m
Deal found 8/30![Southwest logo]()
$607
This Southwest deal was found by Cheapflights users on 8/29. 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 10/235:00 am -
1 stop8h 05m
Mon 10/263:05 pm -
2 stops18h 10m
Deal found 8/29![Southwest logo]()
$616
Last-minute flights from Chicago to St. MaartenDiscover last-minute flight deals from Chicago to St. Maarten. Data last updated September 3, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to St. Maarten. Data last updated September 3, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 8/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:09 am -
1 stop8h 51m
Sat 10/36:00 pm -
1 stop16h 48m
Deal found 8/29![Air Canada logo]()
$429
This Southwest deal was found by Cheapflights users on 8/29. 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 9/285:00 am -
1 stop8h 05m
Mon 10/53:05 pm -
1 stop10h 20m
Deal found 8/29![Southwest logo]()
$537
This Southwest deal was found by Cheapflights users on 8/29. 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 10/15:00 am -
1 stop8h 05m
Fri 10/93:05 pm -
1 stop10h 20m
Deal found 8/29![Southwest logo]()
$566
This Southwest deal was found by Cheapflights users on 8/29. 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
Fri 10/93:05 pm -
1 stop10h 20m
Deal found 8/29![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 8/29. 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 10/35:00 am -
1 stop7h 45m
Sat 10/102:45 pm -
2 stops17h 40m
Deal found 8/29![Southwest logo]()
$525
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:10 pm -
2 stops17h 55m
Sat 10/242:45 pm -
2 stops17h 40m
Deal found 9/2![Southwest logo]()
$545
This Air Canada deal was found by Cheapflights users on 8/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:09 am -
1 stop8h 51m
Mon 10/263:45 pm -
1 stop18h 38m
Deal found 8/31![Air Canada logo]()
$414
This Flightnetwork deal was found by Cheapflights users on 9/1. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:40 pm -
1 stop19h 20m
Sun 11/14:45 pm -
1 stop18h 38m
Deal found 9/1![Air Canada logo]()
$388
This Expedia deal was found by Cheapflights users on 8/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:45 am -
2 stops31h 15m
Mon 10/263:45 pm -
1 stop29h 28m
Deal found 8/29![Air Canada logo]()
$412
This Air Canada deal was found by Cheapflights users on 8/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:40 pm -
1 stop17h 05m
Sat 10/312:40 pm -
1 stop26h 12m
Deal found 8/30![Air Canada logo]()
$404
This Air Canada deal was found by Cheapflights users on 8/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2510:57 am -
2 stops26h 48m
Sat 10/312:40 pm -
1 stop26h 12m
Deal found 8/31![Air Canada logo]()
$409
This Southwest deal was found by Cheapflights users on 8/29. 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 10/295:00 am -
1 stop8h 05m
Tue 11/33:20 pm -
2 stops16h 20m
Deal found 8/29![Southwest logo]()
$571
One-way flights from Chicago to St. MaartenSearch for one-way flight options from Chicago to St. Maarten. Find affordable one-way fares based on user searches. Data last updated September 3, 2026.
Search for one-way flight options from Chicago to St. Maarten. Find affordable one-way fares based on user searches. Data last updated September 3, 2026.
This Trip.com deal was found by Cheapflights users on 8/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:45 pm -
1 stop24h 15m
Deal found 8/30![Air Canada logo]()
$137
This Orbitz deal was found by Cheapflights users on 8/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/271:55 pm -
1 stop22h 50m
Deal found 8/29![Air Canada logo]()
$158
This Expedia deal was found by Cheapflights users on 8/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:40 pm -
2 stops48h 20m
Deal found 8/31![Air Canada logo]()
$166
This Air Canada deal was found by Cheapflights users on 8/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/305:35 pm -
1 stop22h 25m
Deal found 8/30![Air Canada logo]()
$167
This Air Canada deal was found by Cheapflights users on 8/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:09 am -
1 stop8h 51m
Deal found 8/31![Air Canada logo]()
$168
This Air Canada deal was found by Cheapflights users on 8/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:11 am -
2 stops32h 49m
Deal found 8/31![Air Canada logo]()
$171
This Air Canada deal was found by Cheapflights users on 9/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:55 pm -
1 stop22h 50m
Deal found 9/1![Air Canada logo]()
$173
This JetBlue deal was found by Cheapflights users on 8/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:00 am -
1 stop7h 00m
Deal found 8/30![JetBlue logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 8/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
1 stop7h 00m
Deal found 8/29![JetBlue logo]()
$176
This Air Canada deal was found by Cheapflights users on 9/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/313:45 pm -
2 stops23h 00m
Deal found 9/1![Air Canada logo]()
$179
This Southwest deal was found by Cheapflights users on 8/29. 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 12/75:20 am -
1 stop7h 00m
Deal found 8/29![Southwest logo]()
$189
This Delta deal was found by Cheapflights users on 8/31. 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 11/96:00 am -
1 stop6h 40m
Deal found 8/31![Delta logo]()
$202
Find flight deals from Chicago to St. Maarten
Keep the following information in mind while searching for Chicago to St. Maarten flight deals. Data was last updated September 3, 2026.
Round-trip from | $388 (Flightnetwork) |
|---|---|
One-way from | $137 (Trip.com) |
Popular in | June |
Cheapest in | January |
Average price | $670 |
Good round-trip deal | $740 or less |
Good one-way deal | $414 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 3, 2026.
Use the filters below to find and compare flights from Chicago 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
Sun 11/8
8:25 pm-3:40 pm
2 stops17h 15m
Simpson Bay Princess Juliana
Fri 11/13
4:40 pm-11:05 pm
1 stop8h 25m
$472
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Fri 11/27
4:00 pm-1:30 pm
2 stops19h 30m
Simpson Bay Princess Juliana
Thu 12/3
3:20 pm-12:05 pm
2 stops22h 45m
$472
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Sun 1/24
5:45 am-2:35 pm
1 stop6h 50m
Simpson Bay Princess Juliana
Sun 2/28
4:15 pm-11:05 pm
1 stop8h 50m
$527
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Thu 12/17
5:10 am-3:40 pm
1 stop8h 30m
Simpson Bay Princess Juliana
Mon 12/21
4:40 pm-10:45 am
2 stops20h 05m
$542
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Wed 12/2
5:20 am-2:20 pm
1 stop7h 00m
Simpson Bay Princess Juliana
Sun 12/6
4:40 pm-11:05 pm
1 stop8h 25m
$544
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Sat 10/17
7:10 pm-2:05 pm
2 stops17h 55m
Simpson Bay Princess Juliana
Sat 10/24
2:45 pm-7:25 am
2 stops17h 40m
$545
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Sat 9/26
5:00 am-12:55 pm
1 stop6h 55m
Simpson Bay Princess Juliana
Sat 10/3
2:45 pm-7:25 am
2 stops17h 40m
$578
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-12:25 am
1 stop10h 20m
$607
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Fri 10/23
5:00 am-2:05 pm
1 stop8h 05m
Simpson Bay Princess Juliana
Mon 10/26
3:05 pm-8:15 am
2 stops18h 10m
$616
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Sat 2/20
8:45 am-3:57 pm
Nonstop5h 12m
Simpson Bay Princess Juliana
Fri 2/26
2:52 pm-7:31 am
1 stop18h 39m
$654
Showing 1-10 of 31 resultsSorted by cheapest first
Best time to book a flight from Chicago to St. Maarten
Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Chicago with our price prediction graph.
MDW-SXM
ORD-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 to St. Maarten
CHI-SX0
MDW-SXM
ORD-SXM
What is the cheapest month to book a flight from Chicago to St. Maarten?
Currently, February is the cheapest month in which you can book a flight from Chicago to St. Maarten (average of $512). Flying from Chicago to St. Maarten in June is currently the most expensive (average of $790). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How often are flights from Chicago to St. Maarten delayed?
About 25% of weekly flights between Chicago and St. Maarten have experienced delays in the past year, with the average delay time being 105 minutes.
What is the most punctual flight time for Chicago to St. Maarten flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to St. Maarten flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 21% of flights being delayed.
How far ahead should I book a flight from Chicago to St. Maarten?
To ensure you get the cheapest price possible for a flight from Chicago to St. Maarten, you should look to book at least 52 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 September 3, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Chicago 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.
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentCourtney,Sep 2026
DEN - STL
Related info for your journey
Find useful and relevant information for your journey from Chicago 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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Alternative routes for Chicago to St. Maarten
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Complete your trip
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Search flights from Chicago to St. Maarten by cabin class
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Chicago and St. Maarten flights
Browse other Chicago and St. Maarten flight options. Last updated on September 3, 2026.
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Top 5 airlines flying from Chicago to St. Maarten
Discover the top 5 airlines that operate flights from Chicago 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 7,457,451 searches. Data last updated September 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$240 | Average$392 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$389 | Average$711 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$389 | Average$728 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$487 | Average$613 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$501 | Average$759 | FlexibilityNo cancel fee | On-time71% |