$143+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Sep 4 — Sep 111
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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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 Chicago to St. Maarten
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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 August 5, 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 August 5, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am -
1 stop7h 00m
Fri 9/253:05 pm -
1 stop9h 03m
Deal found 7/31![JetBlue logo]()
$372
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am -
1 stop7h 00m
Thu 9/173:05 pm -
1 stop9h 03m
Deal found 7/31![JetBlue logo]()
$375
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am -
1 stop7h 00m
Sat 9/263:05 pm -
1 stop9h 03m
Deal found 7/31![JetBlue logo]()
$408
This Gotogate deal was found by Cheapflights users on 8/1. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:55 am -
1 stop30h 05m
Sat 9/196:00 pm -
1 stop23h 58m
Deal found 8/1![Air Canada logo]()
$409
This Air Canada deal was found by Cheapflights users on 7/31. 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.
Sat 10/245:35 pm -
1 stop20h 10m
Sat 10/312:40 pm -
1 stop26h 12m
Deal found 7/31![Air Canada logo]()
$416
This Orbitz deal was found by Cheapflights users on 8/3. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:15 pm -
1 stop25h 45m
Sun 10/253:45 pm -
1 stop18h 38m
Deal found 8/3![Air Canada logo]()
$421
This Air Canada deal was found by Cheapflights users on 8/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:40 pm -
1 stop19h 20m
Sat 10/36:00 pm -
1 stop16h 00m
Deal found 8/2![Air Canada logo]()
$423
This Priceline deal was found by Cheapflights users on 7/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:21 pm -
2 stops21h 39m
Fri 9/253:05 pm -
1 stop9h 03m
Deal found 7/31![Multiple Airlines logo]()
$424
This Air Canada deal was found by Cheapflights users on 7/31. 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 11/273:45 pm -
1 stop21h 00m
Thu 12/33:45 pm -
1 stop25h 07m
Deal found 7/31![Air Canada logo]()
$425
This Southwest deal was found by Cheapflights users on 7/31. 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.
Mon 9/145:00 am -
1 stop8h 05m
Thu 9/173:05 pm -
1 stop8h 40m
Deal found 7/31![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 8/4. 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 11/275:05 am -
1 stop7h 15m
Thu 12/33:20 pm -
2 stops16h 20m
Deal found 8/4![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 8/2. 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 9/56:15 pm -
2 stops18h 50m
Sat 9/121:55 pm -
1 stop8h 05m
Deal found 8/2![Southwest logo]()
$531
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 August 5, 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 August 5, 2026.
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am -
1 stop7h 00m
Thu 9/173:05 pm -
1 stop9h 03m
Deal found 7/31![JetBlue logo]()
$375
This Southwest deal was found by Cheapflights users on 7/31. 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.
Sun 9/135:25 am -
1 stop7h 40m
Thu 9/173:05 pm -
1 stop8h 40m
Deal found 7/31![Southwest logo]()
$467
This Copa Airlines deal was found by Cheapflights users on 8/3. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:01 am -
1 stop26h 32m
Mon 10/2612:35 pm -
1 stop13h 30m
Deal found 8/3![Copa Airlines logo]()
$603
This Delta deal was found by Cheapflights users on 7/31. 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.
Wed 9/235:30 am -
1 stop7h 23m
Sun 9/273:18 pm -
1 stop9h 41m
Deal found 7/31![Delta logo]()
$665
This American Airlines deal was found by Cheapflights users on 8/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:59 pm -
1 stop18h 23m
Tue 9/84:39 pm -
1 stop16h 09m
Deal found 8/4![American Airlines logo]()
$750
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am -
1 stop7h 00m
Sat 9/263:05 pm -
1 stop9h 03m
Deal found 7/31![JetBlue logo]()
$408
This Southwest deal was found by Cheapflights users on 8/3. 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 11/276:30 pm -
2 stops17h 00m
Thu 12/33:20 pm -
2 stops16h 20m
Deal found 8/3![Southwest logo]()
$524
This Southwest deal was found by Cheapflights users on 8/4. 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.
Wed 1/205:45 am -
1 stop6h 50m
Sun 1/243:35 pm -
1 stop9h 15m
Deal found 8/4![Southwest logo]()
$550
This Delta deal was found by Cheapflights users on 8/2. 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.
Wed 9/165:30 am -
1 stop7h 23m
Wed 9/233:18 pm -
1 stop9h 41m
Deal found 8/2![Delta logo]()
$665
This Southwest deal was found by Cheapflights users on 7/31. 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.
Mon 9/145:00 am -
1 stop8h 05m
Thu 9/173:05 pm -
1 stop8h 40m
Deal found 7/31![Southwest logo]()
$559
This Delta deal was found by Cheapflights users on 8/2. 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.
Fri 9/48:48 am -
2 stops28h 05m
Wed 9/93:18 pm -
2 stops17h 38m
Deal found 8/2![Delta logo]()
$670
This Southwest deal was found by Cheapflights users on 8/1. 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 10/17:35 pm -
2 stops17h 30m
Mon 10/53:05 pm -
1 stop10h 15m
Deal found 8/1![Southwest logo]()
$576
This Southwest deal was found by Cheapflights users on 7/31. 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 9/187:55 pm -
2 stops16h 00m
Sat 9/261:55 pm -
1 stop9h 50m
Deal found 7/31![Southwest logo]()
$610
This Delta deal was found by Cheapflights users on 8/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:30 am -
1 stop7h 23m
Sat 9/193:18 pm -
1 stop9h 41m
Deal found 8/4![Delta logo]()
$745
This Delta deal was found by Cheapflights users on 8/2. 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.
Mon 9/75:30 am -
1 stop7h 23m
Fri 9/113:18 pm -
1 stop9h 41m
Deal found 8/2![Delta logo]()
$745
This Southwest deal was found by Cheapflights users on 8/2. 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.
Tue 11/178:50 pm -
2 stops15h 30m
Sat 11/213:50 pm -
1 stop9h 10m
Deal found 8/2![Southwest logo]()
$647
This Delta deal was found by Cheapflights users on 8/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:30 am -
1 stop7h 23m
Thu 9/173:18 pm -
2 stops17h 38m
Deal found 8/4![Delta logo]()
$750
This Southwest deal was found by Cheapflights users on 8/2. 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 11/145:00 am -
1 stop7h 20m
Sat 11/213:50 pm -
1 stop9h 10m
Deal found 8/2![Southwest logo]()
$649
This Southwest deal was found by Cheapflights users on 8/2. 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.
Fri 10/95:00 am -
1 stop8h 05m
Mon 10/123:05 pm -
1 stop10h 15m
Deal found 8/2![Southwest logo]()
$710
Last-minute flights from Chicago to St. MaartenDiscover last-minute flight deals from Chicago to St. Maarten. Data last updated August 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to St. Maarten. Data last updated August 5, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/2. 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 9/56:15 pm -
2 stops18h 50m
Sat 9/121:55 pm -
1 stop8h 05m
Deal found 8/2![Southwest logo]()
$531
This Gotogate deal was found by Cheapflights users on 8/1. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:55 am -
1 stop30h 05m
Sat 9/196:00 pm -
1 stop23h 58m
Deal found 8/1![Air Canada logo]()
$409
This Southwest deal was found by Cheapflights users on 7/31. 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.
Sun 9/138:45 pm -
2 stops16h 20m
Thu 9/173:05 pm -
1 stop8h 40m
Deal found 7/31![Southwest logo]()
$472
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am -
1 stop7h 00m
Thu 9/173:05 pm -
1 stop9h 03m
Deal found 7/31![JetBlue logo]()
$375
This Southwest deal was found by Cheapflights users on 7/31. 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.
Mon 9/145:00 am -
1 stop8h 05m
Thu 9/173:05 pm -
1 stop8h 40m
Deal found 7/31![Southwest logo]()
$467
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am -
1 stop7h 00m
Fri 9/253:05 pm -
1 stop9h 03m
Deal found 7/31![JetBlue logo]()
$372
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am -
1 stop7h 00m
Sat 9/263:05 pm -
1 stop9h 03m
Deal found 7/31![JetBlue logo]()
$408
This Priceline deal was found by Cheapflights users on 7/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:21 pm -
2 stops21h 39m
Fri 9/253:05 pm -
1 stop9h 03m
Deal found 7/31![Multiple Airlines logo]()
$424
This Southwest deal was found by Cheapflights users on 8/4. 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 9/187:55 pm -
2 stops16h 00m
Mon 9/213:05 pm -
1 stop8h 40m
Deal found 8/4![Southwest logo]()
$524
This Southwest deal was found by Cheapflights users on 7/31. 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 9/185:00 am -
1 stop8h 05m
Sat 9/261:55 pm -
1 stop8h 05m
Deal found 7/31![Southwest logo]()
$536
This Air Canada deal was found by Cheapflights users on 8/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:40 pm -
1 stop19h 20m
Sat 10/36:00 pm -
1 stop16h 00m
Deal found 8/2![Air Canada logo]()
$423
This Air Canada deal was found by Cheapflights users on 7/31. 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.
Sat 9/267:09 am -
1 stop8h 51m
Sat 10/36:00 pm -
1 stop16h 00m
Deal found 7/31![Air Canada logo]()
$427
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 August 5, 2026.
Search for one-way flight options from Chicago to St. Maarten. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am -
1 stop7h 00m
Deal found 7/31![JetBlue logo]()
$143
This Orbitz deal was found by Cheapflights users on 8/1. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:45 pm -
1 stop24h 15m
Deal found 8/1![Air Canada logo]()
$170
This Air Canada deal was found by Cheapflights users on 8/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:21 pm -
2 stops45h 39m
Deal found 8/2![Air Canada logo]()
$174
This Air Canada deal was found by Cheapflights users on 8/1. 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.
Thu 10/16:21 pm -
2 stops45h 39m
Deal found 8/1![Air Canada logo]()
$175
This Air Canada deal was found by Cheapflights users on 8/1. 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.
Fri 10/303:45 pm -
1 stop20h 55m
Deal found 8/1![Air Canada logo]()
$176
This Expedia deal was found by Cheapflights users on 8/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:05 am -
2 stops30h 40m
Deal found 8/1![Air Canada logo]()
$179
This Air Canada deal was found by Cheapflights users on 8/1. 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 10/311:57 pm -
1 stop24h 48m
Deal found 8/1![Air Canada logo]()
$181
This Air Canada deal was found by Cheapflights users on 8/1. 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.
Mon 11/25:54 pm -
2 stops43h 51m
Deal found 8/1![Air Canada logo]()
$184
This JetBlue deal was found by Cheapflights users on 8/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:20 pm -
1 stop14h 13m
Deal found 8/3![JetBlue logo]()
$189
This Southwest deal was found by Cheapflights users on 8/2. 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 11/18:25 pm -
2 stops17h 15m
Deal found 8/2![Southwest logo]()
$195
This Cheapflightsfares deal was found by Cheapflights users on 8/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:30 pm -
1 stop14h 34m
Deal found 8/2![JetBlue logo]()
$204
This Southwest deal was found by Cheapflights users on 8/2. 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 10/189:20 pm -
2 stops15h 45m
Deal found 8/2![Southwest logo]()
$212
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 August 5, 2026.
Round-trip from | $372 (Cheapflightsfares) |
|---|---|
One-way from | $143 (JetBlue) |
Popular in | June |
Cheapest in | January |
Average price | $672 |
Good round-trip deal | $745 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 2,558,603 searches. Data last updated August 5, 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
Quickest round-trip
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Mon 9/14
6:00 am-2:00 pm
1 stop7h 00m
Simpson Bay Princess Juliana
Thu 9/17
3:05 pm-11:08 pm
1 stop9h 03m
$375
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Fri 9/18
6:00 am-2:00 pm
1 stop7h 00m
Simpson Bay Princess Juliana
Sat 9/26
3:05 pm-11:08 pm
1 stop9h 03m
$408
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Sun 9/13
5:25 am-2:05 pm
1 stop7h 40m
Simpson Bay Princess Juliana
Thu 9/17
3:05 pm-10:45 pm
1 stop8h 40m
$467
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 11/27
6:30 pm-1:30 pm
2 stops17h 00m
Simpson Bay Princess Juliana
Thu 12/3
3:20 pm-5:40 am
2 stops16h 20m
$524
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Wed 1/20
5:45 am-2:35 pm
1 stop6h 50m
Simpson Bay Princess Juliana
Sun 1/24
3:35 pm-10:50 pm
1 stop9h 15m
$550
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Mon 9/14
5:00 am-2:05 pm
1 stop8h 05m
Simpson Bay Princess Juliana
Thu 9/17
3:05 pm-10:45 pm
1 stop8h 40m
$559
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Thu 10/1
7:35 pm-2:05 pm
2 stops17h 30m
Simpson Bay Princess Juliana
Mon 10/5
3:05 pm-12:20 am
1 stop10h 15m
$576
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Thu 10/22
8:01 am-11:33 am
1 stop26h 32m
Simpson Bay Princess Juliana
Mon 10/26
12:35 pm-1:05 am
1 stop13h 30m
$603
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 9/18
7:55 pm-12:55 pm
2 stops16h 00m
Simpson Bay Princess Juliana
Sat 9/26
1:55 pm-10:45 pm
1 stop9h 50m
$610
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Tue 11/17
8:50 pm-2:20 pm
2 stops15h 30m
Simpson Bay Princess Juliana
Sat 11/21
3:50 pm-11:00 pm
1 stop9h 10m
$647
Showing 1-10 of 38 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.
ORD-SXM
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 to St. Maarten
CHI-SX0
ORD-SXM
MDW-SXM
What is the cheapest month to book a flight from Chicago to St. Maarten?
Currently, September is the cheapest month in which you can book a flight from Chicago to St. Maarten (average of $420). Flying from Chicago to St. Maarten in June is currently the most expensive (average of $785). 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 26% of weekly flights between Chicago and St. Maarten have experienced delays in the past year, with the average delay time being 103 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 Tuesday 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 August 5, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican 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.
Overall
7.8
Entertainment
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.8
Entertainment
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.8
Entertainment
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.8
Entertainment
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.8
Entertainment
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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
Complete your trip to St. Maarten by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to St. Maarten by cabin class
Find flights from Chicago to St. Maarten, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and St. Maarten flights
Browse other Chicago and St. Maarten flight options. Last updated on August 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated August 5, 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$763 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$487 | Average$617 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$500 | Average$729 | FlexibilityNo cancel fee | On-time71% |