$177+ Cheap flights from Chicago (CHI) to St. Maarten
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Dec 5 — Dec 121
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 November 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 November 5, 2026.
This Air Canada deal was found by Cheapflights users on 11/1. 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 12/54:30 pm -
1 stop21h 20m
Fri 12/114:50 pm -
1 stop18h 18m
Deal found 11/1![Air Canada logo]()
$439
This Gotogate deal was found by Cheapflights users on 11/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/254:30 pm -
2 stops20h 15m
Fri 12/44:50 pm -
1 stop18h 18m
Deal found 11/2![Air Canada logo]()
$443
This Air Canada deal was found by Cheapflights users on 10/31. 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 11/295:58 pm -
2 stops19h 47m
Thu 12/33:30 pm -
2 stops28h 50m
Deal found 10/31![Air Canada logo]()
$444
This Air Canada deal was found by Cheapflights users on 11/1. 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 12/53:45 pm -
2 stops22h 05m
Sat 12/123:45 pm -
2 stops19h 23m
Deal found 11/1![Air Canada logo]()
$446
This Justfly.com deal was found by Cheapflights users on 10/31. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:15 am -
2 stops26h 30m
Tue 12/13:45 pm -
2 stops28h 35m
Deal found 10/31![Air Canada logo]()
$447
This Gotogate deal was found by Cheapflights users on 11/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/273:40 pm -
1 stop21h 05m
Sat 12/53:45 pm -
2 stops19h 23m
Deal found 11/2![Air Canada logo]()
$451
This Justfly.com deal was found by Cheapflights users on 11/1. 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.
Tue 12/19:21 pm -
2 stops39h 14m
Mon 12/74:50 pm -
1 stop24h 48m
Deal found 11/1![Air Canada logo]()
$452
This Expedia deal was found by Cheapflights users on 11/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:20 am -
2 stops29h 15m
Mon 12/74:50 pm -
1 stop26h 53m
Deal found 11/3![Air Canada logo]()
$458
This Southwest deal was found by Cheapflights users on 10/31. 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 12/209:05 pm -
2 stops16h 35m
Thu 12/243:15 pm -
2 stops22h 50m
Deal found 10/31![Southwest logo]()
$622
This Southwest deal was found by Cheapflights users on 11/4. 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 12/24:10 pm -
2 stops20h 05m
Wed 12/93:15 pm -
2 stops22h 50m
Deal found 11/4![Southwest logo]()
$627
This Southwest deal was found by Cheapflights users on 11/2. 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 12/135:05 am -
1 stop7h 10m
Sat 12/194:40 pm -
1 stop8h 25m
Deal found 11/2![Southwest logo]()
$638
This Southwest deal was found by Cheapflights users on 11/2. 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 12/125:00 am -
1 stop7h 15m
Fri 12/184:40 pm -
1 stop8h 35m
Deal found 11/2![Southwest logo]()
$646
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 November 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 November 5, 2026.
This Travelocity deal was found by Cheapflights users on 11/4. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/38:45 am -
1 stop29h 05m
Wed 12/164:50 pm -
1 stop24h 48m
Deal found 11/4![Air Canada logo]()
$457
This Delta deal was found by Cheapflights users on 11/4. 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.
Sun 1/317:59 pm -
1 stop16h 58m
Wed 2/34:23 pm -
1 stop19h 37m
Deal found 11/4![Delta logo]()
$593
This United Airlines deal was found by Cheapflights users on 11/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/238:40 am -
Nonstop5h 17m
Mon 12/282:10 pm -
Nonstop6h 01m
Deal found 11/2![United Airlines logo]()
$623
This Copa Airlines deal was found by Cheapflights users on 10/31. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/272:13 pm -
1 stop19h 12m
Sat 3/612:23 pm -
1 stop13h 21m
Deal found 10/31![Copa Airlines logo]()
$624
This Southwest deal was found by Cheapflights users on 11/3. 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.
Sun 1/245:25 am -
1 stop6h 50m
Sun 1/314:40 pm -
1 stop8h 20m
Deal found 11/3![Southwest logo]()
$646
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/106:00 pm -
1 stop16h 20m
Tue 1/264:23 pm -
1 stop19h 37m
Deal found 11/3![Delta logo]()
$593
This Expedia deal was found by Cheapflights users on 11/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/23:45 pm -
1 stop20h 35m
Sun 4/112:45 pm -
1 stop19h 20m
Deal found 11/4![Air Canada logo]()
$603
This Copa Airlines deal was found by Cheapflights users on 10/31. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/62:13 pm -
1 stop19h 13m
Sat 3/1312:23 pm -
1 stop26h 11m
Deal found 10/31![Copa Airlines logo]()
$639
This United Airlines deal was found by Cheapflights users on 11/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/308:40 am -
Nonstop5h 17m
Wed 2/32:52 pm -
1 stop18h 59m
Deal found 11/2![United Airlines logo]()
$640
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/212:42 pm -
2 stops21h 38m
Tue 2/94:23 pm -
2 stops23h 04m
Deal found 11/3![Delta logo]()
$597
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Thu 12/33:35 pm -
2 stops20h 40m
Wed 12/163:15 pm -
2 stops22h 35m
Deal found 11/4![Southwest logo]()
$661
This Copa Airlines deal was found by Cheapflights users on 11/2. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/33:13 pm -
1 stop19h 13m
Sat 4/1012:23 pm -
1 stop26h 11m
Deal found 11/2![Copa Airlines logo]()
$639
This United Airlines deal was found by Cheapflights users on 11/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/159:47 pm -
1 stop14h 03m
Tue 1/192:52 pm -
1 stop18h 59m
Deal found 11/2![United Airlines logo]()
$645
This Southwest deal was found by Cheapflights users on 11/4. 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 2/58:50 pm -
2 stops16h 50m
Tue 2/93:15 pm -
2 stops21h 00m
Deal found 11/4![Southwest logo]()
$674
This Delta deal was found by Cheapflights users on 11/4. 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.
Fri 2/56:00 am -
1 stop6h 57m
Tue 2/91:50 pm -
1 stop12h 05m
Deal found 11/4![Delta logo]()
$645
This United Airlines deal was found by Cheapflights users on 11/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/238:40 am -
Nonstop5h 17m
Sat 1/302:10 pm -
Nonstop6h 01m
Deal found 11/3![United Airlines logo]()
$682
This Southwest deal was found by Cheapflights users on 11/2. 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 11/275:10 am -
1 stop8h 30m
Sat 12/53:15 pm -
1 stop8h 25m
Deal found 11/2![Southwest logo]()
$707
This Delta deal was found by Cheapflights users on 10/31. 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.
Sat 12/56:00 am -
1 stop6h 45m
Fri 12/114:05 pm -
1 stop8h 49m
Deal found 10/31![Delta logo]()
$669
This Southwest deal was found by Cheapflights users on 11/1. 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 12/118:25 pm -
2 stops15h 50m
Sat 12/193:15 pm -
2 stops19h 25m
Deal found 11/1![Southwest logo]()
$712
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 am -
1 stop6h 45m
Sat 12/191:40 pm -
1 stop10h 42m
Deal found 11/3![Delta logo]()
$689
This Delta deal was found by Cheapflights users on 11/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:00 am -
1 stop6h 45m
Sat 12/123:36 pm -
1 stop9h 18m
Deal found 11/1![Delta logo]()
$689
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 am -
1 stop6h 45m
Sun 12/201:40 pm -
1 stop10h 42m
Deal found 11/2![Delta logo]()
$689
Last-minute flights from Chicago to St. MaartenDiscover last-minute flight deals from Chicago to St. Maarten. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to St. Maarten. Data last updated November 5, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 11/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/254:30 pm -
2 stops20h 15m
Fri 12/44:50 pm -
1 stop18h 18m
Deal found 11/2![Air Canada logo]()
$443
This Justfly.com deal was found by Cheapflights users on 10/31. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:15 am -
2 stops26h 30m
Tue 12/13:45 pm -
2 stops28h 35m
Deal found 10/31![Air Canada logo]()
$447
This Gotogate deal was found by Cheapflights users on 11/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/273:40 pm -
1 stop21h 05m
Sat 12/53:45 pm -
2 stops19h 23m
Deal found 11/2![Air Canada logo]()
$451
This Air Canada deal was found by Cheapflights users on 10/31. 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 11/295:58 pm -
2 stops19h 47m
Thu 12/33:30 pm -
2 stops28h 50m
Deal found 10/31![Air Canada logo]()
$444
This Justfly.com deal was found by Cheapflights users on 11/1. 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.
Tue 12/19:21 pm -
2 stops39h 14m
Mon 12/74:50 pm -
1 stop24h 48m
Deal found 11/1![Air Canada logo]()
$452
This Expedia deal was found by Cheapflights users on 11/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:20 am -
2 stops29h 15m
Mon 12/74:50 pm -
1 stop26h 53m
Deal found 11/3![Air Canada logo]()
$458
This Southwest deal was found by Cheapflights users on 11/4. 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 12/24:10 pm -
2 stops20h 05m
Wed 12/93:15 pm -
2 stops22h 50m
Deal found 11/4![Southwest logo]()
$627
This Air Canada deal was found by Cheapflights users on 11/1. 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 12/54:30 pm -
1 stop21h 20m
Fri 12/114:50 pm -
1 stop18h 18m
Deal found 11/1![Air Canada logo]()
$439
This Air Canada deal was found by Cheapflights users on 11/1. 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 12/53:45 pm -
2 stops22h 05m
Sat 12/123:45 pm -
2 stops19h 23m
Deal found 11/1![Air Canada logo]()
$446
This Southwest deal was found by Cheapflights users on 11/2. 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 12/125:00 am -
1 stop7h 15m
Fri 12/184:40 pm -
1 stop8h 35m
Deal found 11/2![Southwest logo]()
$646
This Southwest deal was found by Cheapflights users on 11/2. 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 12/135:05 am -
1 stop7h 10m
Sat 12/194:40 pm -
1 stop8h 25m
Deal found 11/2![Southwest logo]()
$638
This Southwest deal was found by Cheapflights users on 10/31. 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 12/209:05 pm -
2 stops16h 35m
Thu 12/243:15 pm -
2 stops22h 50m
Deal found 10/31![Southwest logo]()
$622
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 November 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 November 5, 2026.
This Trip.com deal was found by Cheapflights users on 11/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:45 am -
1 stop29h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Air Canada logo]()
$177
This Air Canada deal was found by Cheapflights users on 10/31. 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.
Mon 12/77:20 am -
2 stops29h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Air Canada logo]()
$178
This Travelocity deal was found by Cheapflights users on 10/31. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/53:45 pm -
2 stops22h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Air Canada logo]()
$181
This Air Canada deal was found by Cheapflights users on 11/1. 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.
Sun 11/2910:15 am -
1 stop27h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Air Canada logo]()
$183
This Air Canada deal was found by Cheapflights users on 10/31. 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.
Mon 11/3011:05 am -
2 stops25h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Air Canada logo]()
$186
This Expedia deal was found by Cheapflights users on 11/1. 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.
Mon 1/257:05 am -
1 stop29h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Air Canada logo]()
$209
This Trip.com deal was found by Cheapflights users on 10/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2412:50 pm -
1 stop23h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Air Canada logo]()
$210
This Orbitz deal was found by Cheapflights users on 11/1. 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.
Sun 1/248:50 pm -
1 stop16h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Air Canada logo]()
$214
This Southwest deal was found by Cheapflights users on 10/31. 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.
Tue 12/88:50 pm -
2 stops15h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Southwest logo]()
$240
This Delta deal was found by Cheapflights users on 11/2. 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 1/116:00 am -
1 stop6h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$248
This Southwest deal was found by Cheapflights users on 10/31. 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 11/309:05 pm -
2 stops15h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 11/2. 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.
Wed 12/309:05 pm -
2 stops15h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Southwest logo]()
$286
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 November 5, 2026.
Round-trip from | $439 (Travelocity) |
|---|---|
One-way from | $177 (Trip.com) |
Popular in | June |
Cheapest in | January |
Average price | $690 |
Good round-trip deal | $764 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 November 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
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Sat 12/5
3:45 pm-3:50 pm
2 stops22h 05m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Tue 1/12
7:50 pm-2:15 pm
2 stops16h 25m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$240
Quickest round-trip
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Wed 12/23
8:40 am-3:57 pm
Nonstop5h 17m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$244
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Mon 1/11
6:00 am-2:57 pm
1 stop6h 57m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$248
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Mon 11/30
5:25 am-3:40 pm
1 stop8h 15m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$248
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Mon 1/11
1:45 pm-2:57 pm
2 stops23h 12m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$248
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Wed 12/30
9:47 pm-1:07 pm
1 stop13h 20m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$248
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Tue 12/22
5:25 am-2:49 pm
1 stop7h 24m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$248
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Tue 1/12
3:01 pm-12:20 pm
2 stops19h 19m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$248
ChicagoSimpson Bay
MDW Chicago Midway - SXM Simpson Bay Princess Juliana
MDWSXM
Chicago Midway
Wed 12/30
9:05 pm-2:15 pm
2 stops15h 10m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$286
Showing 1-10 of 42 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, February is the cheapest month in which you can book a flight from Chicago to St. Maarten (average of $565). Flying from Chicago to St. Maarten in December is currently the most expensive (average of $784). 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.
What is the cheapest time of day to fly from CHI to SX?
Find hourly flight availability from Chicago to St. Maarten. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 5, 2026.
When flying from Chicago to St. Maarten, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 19 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 November 5, 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.
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
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Complete your trip
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Chicago and St. Maarten flights
Browse other Chicago and St. Maarten flight options. Last updated on November 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Chicago to St. Maarten
Discover the top 4 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 November 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$240 | Average$595 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$389 | Average$722 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$501 | Average$769 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$516 | Average$782 | FlexibilityNo cancel fee | On-time69% |