$150+ 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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Jul 9 — Jul 161
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to St. Maarten with Cheapflights
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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 June 9, 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 June 9, 2026.
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am
ORD
- SXM
1 stop7h 00m
JetBlue
Fri 9/253:05 pm
SXM
- ORD
1 stop9h 26m
JetBlue
Deal found 6/7![JetBlue logo]()
$365
This Cheapflightsfares deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 am
ORD
- SXM
1 stop7h 00m
JetBlue
Mon 9/143:05 pm
SXM
- ORD
1 stop9h 26m
JetBlue
Deal found 6/7![JetBlue logo]()
$384
This Travelocity deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:00 am
ORD
- SXM
1 stop7h 00m
JetBlue
Sat 9/193:05 pm
SXM
- ORD
1 stop9h 26m
JetBlue
Deal found 6/6![JetBlue logo]()
$389
This Expedia deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:15 pm
ORD
- SXM
1 stop25h 45m
Multiple Airlines
Thu 7/91:42 pm
SXM
- ORD
1 stop11h 02m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$403
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:10 am
MDW
- SXM
1 stop7h 15m
Southwest
Tue 7/143:00 pm
SXM
- MDW
1 stop8h 05m
Southwest
Deal found 6/7![Southwest logo]()
$415
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/205:10 am
MDW
- SXM
1 stop7h 15m
Southwest
Wed 7/293:00 pm
SXM
- MDW
2 stops17h 10m
Southwest
Deal found 6/7![Southwest logo]()
$420
This Super.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
ORD
- SXM
1 stop9h 16m
JetBlue
Sat 8/221:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 6/7![JetBlue logo]()
$426
This Flysmarter deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:22 pm
ORD
- SXM
1 stop15h 43m
JetBlue
Thu 7/91:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 6/7![JetBlue logo]()
$437
This Southwest deal was found by Cheapflights users on 6/4. 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 7/105:10 am
MDW
- SXM
1 stop7h 15m
Southwest
Tue 7/143:00 pm
SXM
- MDW
1 stop8h 05m
Southwest
Deal found 6/4![Southwest logo]()
$442
This Cheapflightsfares deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
ORD
- SXM
1 stop9h 16m
JetBlue
Sat 8/291:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 6/5![JetBlue logo]()
$446
This Super.com deal was found by Cheapflights users on 6/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:30 pm
ORD
- SXM
1 stop14h 37m
JetBlue
Tue 7/141:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 6/8![JetBlue logo]()
$452
This Justfly.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:35 pm
ORD
- SXM
1 stop21h 03m
JetBlue
Fri 9/251:45 pm
SXM
- ORD
1 stop10h 59m
JetBlue
Deal found 6/6![JetBlue logo]()
$455
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 June 9, 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 June 9, 2026.
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:10 am
MDW
- SXM
1 stop7h 15m
Southwest
Tue 7/143:00 pm
SXM
- MDW
1 stop8h 05m
Southwest
Deal found 6/6![Southwest logo]()
$415
This Orbitz deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:45 pm
ORD
- SXM
1 stop20h 50m
Air Canada
Sat 11/73:10 pm
SXM
- ORD
2 stops24h 00m
Air Canada
Deal found 6/7![Air Canada logo]()
$516
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:20 pm
ORD
- SXM
1 stop14h 13m
JetBlue
Thu 7/91:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 6/5![JetBlue logo]()
$536
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Mon 7/66:00 pm
ORD
- SXM
1 stop17h 33m
United Airlines
Mon 7/133:50 pm
SXM
- ORD
1 stop8h 41m
United Airlines
Deal found 6/8![United Airlines logo]()
$665
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:05 am
MDW
- SXM
1 stop6h 45m
Delta
Wed 9/233:20 pm
SXM
- MDW
1 stop8h 05m
Delta
Deal found 6/6![Delta logo]()
$670
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Mon 7/66:59 am
ORD
- SXM
1 stop7h 45m
American Airlines
Mon 7/131:34 pm
SXM
- ORD
2 stops11h 27m
American Airlines
Deal found 6/8![American Airlines logo]()
$697
This Southwest deal was found by Cheapflights users on 6/4. 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 8/285:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Fri 9/43:05 pm
SXM
- MDW
2 stops17h 30m
Southwest
Deal found 6/4![Southwest logo]()
$489
This Southwest deal was found by Cheapflights users on 6/8. 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 7/38:50 pm
MDW
- SXM
2 stops17h 15m
Southwest
Thu 7/92:25 pm
SXM
- MDW
2 stops17h 45m
Southwest
Deal found 6/8![Southwest logo]()
$515
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/38:20 pm
ORD
- SXM
1 stop14h 13m
JetBlue
Wed 7/151:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 6/5![JetBlue logo]()
$589
This Southwest deal was found by Cheapflights users on 6/4. 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 8/285:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Sat 9/51:55 pm
SXM
- MDW
1 stop8h 00m
Southwest
Deal found 6/4![Southwest logo]()
$532
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
ORD
- SXM
1 stop9h 17m
JetBlue
Wed 7/151:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 6/5![JetBlue logo]()
$609
This Delta deal was found by Cheapflights users on 6/8. 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 9/186:05 am
MDW
- SXM
1 stop6h 45m
Delta
Fri 9/253:20 pm
SXM
- MDW
1 stop8h 05m
Delta
Deal found 6/8![Delta logo]()
$670
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Fri 7/39:45 pm
ORD
- SXM
1 stop13h 49m
American Airlines
Thu 7/92:19 pm
SXM
- ORD
1 stop10h 11m
American Airlines
Deal found 6/8![American Airlines logo]()
$697
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:30 am
ORD
- SXM
1 stop7h 20m
Delta
Fri 9/253:20 pm
SXM
- ORD
2 stops25h 54m
Delta
Deal found 6/6![Delta logo]()
$670
This Southwest deal was found by Cheapflights users on 6/4. 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 6/265:10 am
MDW
- SXM
1 stop7h 15m
Southwest
Thu 7/22:25 pm
SXM
- MDW
1 stop11h 15m
Southwest
Deal found 6/4![Southwest logo]()
$567
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
ORD
- SXM
1 stop9h 17m
JetBlue
Sun 7/121:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 6/5![JetBlue logo]()
$637
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:10 pm
ORD
- SXM
2 stops19h 40m
Delta
Fri 9/253:20 pm
SXM
- ORD
2 stops22h 44m
Delta
Deal found 6/6![Delta logo]()
$670
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:05 pm
MDW
- SXM
2 stops21h 00m
Southwest
Sat 8/221:55 pm
SXM
- MDW
1 stop8h 00m
Southwest
Deal found 6/7![Southwest logo]()
$584
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:10 pm
ORD
- SXM
2 stops19h 40m
Delta
Thu 9/243:20 pm
SXM
- ORD
1 stop9h 39m
Delta
Deal found 6/6![Delta logo]()
$670
This Southwest deal was found by Cheapflights users on 6/4. 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.
Sun 10/118:40 pm
MDW
- SXM
2 stops16h 20m
Southwest
Sat 10/172:45 pm
SXM
- MDW
2 stops17h 40m
Southwest
Deal found 6/4![Southwest logo]()
$602
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:10 pm
ORD
- SXM
2 stops19h 40m
Delta
Thu 9/243:20 pm
SXM
- ORD
1 stop9h 39m
Delta
Deal found 6/6![Delta logo]()
$675
This Southwest deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/208:50 pm
MDW
- SXM
2 stops16h 10m
Southwest
Sat 7/252:15 pm
SXM
- MDW
2 stops17h 55m
Southwest
Deal found 6/6![Southwest logo]()
$631
Last-minute flights from Chicago to St. MaartenDiscover last-minute flight deals from Chicago to St. Maarten. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to St. Maarten. Data last updated June 9, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:15 pm
ORD
- SXM
1 stop25h 45m
Multiple Airlines
Thu 7/91:42 pm
SXM
- ORD
1 stop11h 02m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$403
This Flysmarter deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:22 pm
ORD
- SXM
1 stop15h 43m
JetBlue
Thu 7/91:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 6/7![JetBlue logo]()
$437
This Air Canada deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/47:09 am
ORD
- SXM
1 stop8h 51m
Air Canada
Sat 7/116:00 pm
SXM
- ORD
1 stop16h 00m
Air Canada
Deal found 6/5![Air Canada logo]()
$455
This Super.com deal was found by Cheapflights users on 6/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:30 pm
ORD
- SXM
1 stop14h 37m
JetBlue
Tue 7/141:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 6/8![JetBlue logo]()
$452
This Super.com deal was found by Cheapflights users on 6/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/95:27 pm
ORD
- SXM
1 stop15h 40m
JetBlue
Thu 7/161:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 6/4![JetBlue logo]()
$457
This Southwest deal was found by Cheapflights users on 6/4. 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 7/105:10 am
MDW
- SXM
1 stop7h 15m
Southwest
Tue 7/143:00 pm
SXM
- MDW
1 stop8h 05m
Southwest
Deal found 6/4![Southwest logo]()
$442
This Priceline deal was found by Cheapflights users on 6/8. 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 7/105:13 pm
ORD
- SXM
1 stop17h 17m
Multiple Airlines
Tue 7/141:42 pm
SXM
- ORD
1 stop11h 02m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$463
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:10 am
MDW
- SXM
1 stop7h 15m
Southwest
Tue 7/143:00 pm
SXM
- MDW
1 stop8h 05m
Southwest
Deal found 6/7![Southwest logo]()
$415
This Expedia deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:00 am
ORD
- SXM
1 stop9h 22m
Multiple Airlines
Sat 7/256:00 pm
SXM
- ORD
1 stop16h 00m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$475
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/205:10 am
MDW
- SXM
1 stop7h 15m
Southwest
Wed 7/293:00 pm
SXM
- MDW
2 stops17h 10m
Southwest
Deal found 6/7![Southwest logo]()
$420
This Cheapflightsfares deal was found by Cheapflights users on 6/8. 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.
Sat 7/255:27 pm
ORD
- SXM
1 stop19h 27m
JetBlue
Thu 7/301:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 6/8![JetBlue logo]()
$477
This Air Canada deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:40 pm
ORD
- SXM
1 stop19h 20m
Air Canada
Sat 8/86:00 pm
SXM
- ORD
1 stop16h 00m
Air Canada
Deal found 6/7![Air Canada logo]()
$462
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 June 9, 2026.
Search for one-way flight options from Chicago to St. Maarten. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This Southwest deal was found by Cheapflights users on 6/4. 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 8/215:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Deal found 6/4![Southwest logo]()
$150
This Travelocity deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/23:40 pm
ORD
- SXM
2 stops48h 20m
Air Canada
Deal found 6/7![Air Canada logo]()
$174
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:10 am
MDW
- SXM
1 stop7h 15m
Southwest
Deal found 6/5![Southwest logo]()
$176
This JetBlue deal was found by Cheapflights users on 6/9. 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.
Wed 9/26:27 pm
ORD
- SXM
1 stop14h 35m
JetBlue
Deal found 6/9![JetBlue logo]()
$198
This Air Canada deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:15 pm
ORD
- SXM
1 stop25h 45m
Air Canada
Deal found 6/7![Air Canada logo]()
$201
This Southwest deal was found by Cheapflights users on 6/4. 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.
Mon 8/245:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Deal found 6/4![Southwest logo]()
$203
This Justfly.com deal was found by Cheapflights users on 6/4. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:27 pm
ORD
- SXM
1 stop18h 15m
JetBlue
Deal found 6/4![JetBlue logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 6/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:27 pm
ORD
- SXM
1 stop18h 15m
JetBlue
Deal found 6/4![JetBlue logo]()
$217
This Super.com deal was found by Cheapflights users on 6/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:27 pm
ORD
- SXM
1 stop15h 35m
JetBlue
Deal found 6/9![JetBlue logo]()
$220
This JetBlue deal was found by Cheapflights users on 6/8. 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.
Tue 7/76:30 pm
ORD
- SXM
1 stop14h 37m
JetBlue
Deal found 6/8![JetBlue logo]()
$222
This Expedia deal was found by Cheapflights users on 6/4. 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.
Thu 8/275:27 pm
ORD
- SXM
1 stop15h 35m
JetBlue
Deal found 6/4![JetBlue logo]()
$226
This Expedia deal was found by Cheapflights users on 6/4. 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.
Mon 8/247:00 am
ORD
- SXM
1 stop28h 37m
JetBlue
Deal found 6/4![JetBlue logo]()
$227
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 June 9, 2026.
Round-trip from | $403 (Expedia) |
|---|---|
One-way from | $150 (Southwest) |
Popular in | June |
Cheapest in | August |
Average price | $792 |
Good round-trip deal | $700 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 June 9, 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 - SXM
MDWSXM
Chicago Midway
Mon 7/13
5:10 am-1:25 pm
1 stop7h 15m
Simpson Bay Princess Juliana
Tue 7/14
3:00 pm-10:05 pm
1 stop8h 05m
$415
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 8/28
5:00 am-2:05 pm
1 stop8h 05m
Simpson Bay Princess Juliana
Fri 9/4
3:05 pm-7:35 am
2 stops17h 30m
$489
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 7/3
8:50 pm-3:05 pm
2 stops17h 15m
Simpson Bay Princess Juliana
Thu 7/9
2:25 pm-7:10 am
2 stops17h 45m
$515
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 10/24
3:45 pm-1:35 pm
1 stop20h 50m
Simpson Bay Princess Juliana
Sat 11/7
3:10 pm-1:10 pm
2 stops24h 00m
$516
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 8/28
5:00 am-2:05 pm
1 stop8h 05m
Simpson Bay Princess Juliana
Sat 9/5
1:55 pm-8:55 pm
1 stop8h 00m
$532
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Fri 7/3
8:20 pm-11:33 am
1 stop14h 13m
Simpson Bay Princess Juliana
Thu 7/9
1:42 pm-11:44 pm
1 stop11h 02m
$536
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 6/26
5:10 am-1:25 pm
1 stop7h 15m
Simpson Bay Princess Juliana
Thu 7/2
2:25 pm-12:40 am
1 stop11h 15m
$567
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Sat 8/15
4:05 pm-2:05 pm
2 stops21h 00m
Simpson Bay Princess Juliana
Sat 8/22
1:55 pm-8:55 pm
1 stop8h 00m
$584
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Fri 7/3
8:20 pm-11:33 am
1 stop14h 13m
Simpson Bay Princess Juliana
Wed 7/15
1:42 pm-11:44 pm
1 stop11h 02m
$589
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Sun 10/11
8:40 pm-2:00 pm
2 stops16h 20m
Simpson Bay Princess Juliana
Sat 10/17
2:45 pm-7:25 am
2 stops17h 40m
$602
Showing 1-10 of 41 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 $74). Flying from Chicago to St. Maarten in June is currently the most expensive (average of $574). 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 14 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 June 9, 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.
Comfort
7.8
Overall
7.9
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Overall
7.9
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Overall
7.9
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Overall
7.9
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
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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Complete your trip
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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 June 9, 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 June 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$240 | Average$392 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$410 | Average$751 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$425 | Average$731 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$487 | Average$617 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$500 | Average$749 | FlexibilityNo cancel fee | On-time71% |