$100+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
May 7 — May 141
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 April 7, 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 April 7, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/5. 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.
Sun 4/195:05 am
ORD
- SXM
1 stop7h 32m
Spirit Airlines
Thu 4/232:42 pm
SXM
- ORD
1 stop10h 42m
Spirit Airlines
Deal found 4/5![Spirit Airlines logo]()
$254
This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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.
Sat 4/187:15 pm
ORD
- SXM
1 stop17h 22m
Spirit Airlines
Sat 4/252:42 pm
SXM
- ORD
1 stop10h 42m
Spirit Airlines
Deal found 4/2![Spirit Airlines logo]()
$277
This Priceline deal was found by Cheapflights users on 4/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:05 am
ORD
- SXM
1 stop7h 32m
Spirit Airlines
Thu 5/72:35 pm
SXM
- ORD
1 stop9h 40m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$278
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:15 pm
ORD
- SXM
1 stop17h 22m
Spirit Airlines
Thu 4/302:42 pm
SXM
- ORD
1 stop19h 54m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$301
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:21 pm
ORD
- SXM
2 stops19h 34m
Multiple Airlines
Thu 4/302:42 pm
SXM
- ORD
1 stop10h 42m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$310
This Expedia deal was found by Cheapflights users on 4/7. 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 4/188:40 am
ORD
- SXM
2 stops53h 15m
Multiple Airlines
Sat 4/252:42 pm
SXM
- ORD
1 stop10h 42m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 4/5. 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.
Tue 5/58:50 pm
MDW
- SXM
2 stops15h 40m
Southwest
Tue 5/122:25 pm
SXM
- MDW
2 stops18h 10m
Southwest
Deal found 4/5![Southwest logo]()
$520
This FlightHub deal was found by Cheapflights users on 4/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:40 am
MDW
- SXM
1 stop7h 35m
Frontier
Sat 4/114:20 pm
SXM
- MDW
1 stop28h 47m
Frontier
Deal found 4/2![Frontier logo]()
$543
This Southwest deal was found by Cheapflights users on 4/2. 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 5/35:05 am
MDW
- SXM
1 stop8h 20m
Southwest
Fri 5/292:25 pm
SXM
- MDW
1 stop10h 50m
Southwest
Deal found 4/2![Southwest logo]()
$570
This Southwest deal was found by Cheapflights users on 4/6. 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 5/115:35 am
MDW
- SXM
1 stop6h 55m
Southwest
Mon 5/182:25 pm
SXM
- MDW
1 stop10h 50m
Southwest
Deal found 4/6![Southwest logo]()
$590
This Southwest deal was found by Cheapflights users on 4/5. 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.
Sun 5/35:05 am
MDW
- SXM
1 stop8h 20m
Southwest
Sat 5/91:20 pm
SXM
- MDW
1 stop10h 15m
Southwest
Deal found 4/5![Southwest logo]()
$615
This Southwest deal was found by Cheapflights users on 4/5. 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.
Wed 5/136:00 am
MDW
- SXM
1 stop6h 30m
Southwest
Wed 5/202:25 pm
SXM
- MDW
2 stops17h 45m
Southwest
Deal found 4/5![Southwest logo]()
$620
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 April 7, 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 April 7, 2026.
This Justfly.com deal was found by Cheapflights users on 4/6. 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.
Sat 6/137:09 am
ORD
- SXM
1 stop8h 51m
Air Canada
Sat 6/206:00 pm
SXM
- ORD
1 stop20h 22m
Air Canada
Deal found 4/6![Air Canada logo]()
$359
This CheapOair deal was found by Cheapflights users on 4/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:05 am
ORD
- SXM
1 stop7h 25m
Multiple Airlines
Sat 6/136:00 pm
SXM
- ORD
2 stops14h 45m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$459
This Southwest deal was found by Cheapflights users on 4/5. 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.
Tue 5/55:55 am
ORD
- SXM
1 stop6h 35m
Southwest
Tue 5/122:25 pm
SXM
- ORD
1 stop8h 30m
Southwest
Deal found 4/5![Southwest logo]()
$515
This JetBlue deal was found by Cheapflights users on 4/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:31 am
ORD
- SXM
1 stop27h 04m
JetBlue
Sat 4/2512:30 pm
SXM
- ORD
1 stop20h 11m
JetBlue
Deal found 4/4![JetBlue logo]()
$527
This Delta deal was found by Cheapflights users on 4/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/55:15 am
ORD
- SXM
1 stop7h 50m
Delta
Tue 5/123:20 pm
SXM
- ORD
1 stop8h 07m
Delta
Deal found 4/5![Delta logo]()
$665
This Southwest deal was found by Cheapflights users on 4/4. 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 5/35:05 am
MDW
- SXM
1 stop8h 20m
Southwest
Fri 5/292:25 pm
SXM
- MDW
1 stop10h 50m
Southwest
Deal found 4/4![Southwest logo]()
$570
This Southwest deal was found by Cheapflights users on 4/4. 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 5/38:55 pm
MDW
- SXM
2 stops15h 35m
Southwest
Thu 5/282:25 pm
SXM
- MDW
1 stop10h 50m
Southwest
Deal found 4/4![Southwest logo]()
$575
This Delta deal was found by Cheapflights users on 4/3. 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.
Mon 8/35:15 am
ORD
- SXM
1 stop7h 38m
Delta
Wed 8/123:21 pm
SXM
- ORD
1 stop9h 36m
Delta
Deal found 4/3![Delta logo]()
$665
This Southwest deal was found by Cheapflights users on 4/6. 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 5/115:35 am
MDW
- SXM
1 stop6h 55m
Southwest
Mon 5/182:25 pm
SXM
- MDW
1 stop10h 50m
Southwest
Deal found 4/6![Southwest logo]()
$590
This Delta deal was found by Cheapflights users on 4/2. 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.
Tue 5/265:30 am
ORD
- SXM
1 stop7h 21m
Delta
Wed 6/33:20 pm
SXM
- ORD
1 stop9h 48m
Delta
Deal found 4/2![Delta logo]()
$665
This Delta deal was found by Cheapflights users on 4/2. 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.
Tue 5/55:15 am
ORD
- SXM
1 stop7h 50m
Delta
Wed 5/133:20 pm
SXM
- ORD
1 stop18h 19m
Delta
Deal found 4/2![Delta logo]()
$665
This Southwest deal was found by Cheapflights users on 4/5. 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.
Tue 5/265:55 am
ORD
- SXM
1 stop6h 35m
Southwest
Tue 6/22:25 pm
SXM
- ORD
1 stop8h 30m
Southwest
Deal found 4/5![Southwest logo]()
$625
This Delta deal was found by Cheapflights users on 4/5. 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 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
Sun 9/203:20 pm
SXM
- ORD
1 stop9h 37m
Delta
Deal found 4/5![Delta logo]()
$690
This Southwest deal was found by Cheapflights users on 4/4. 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 7/55:20 am
MDW
- SXM
1 stop9h 10m
Southwest
Fri 7/102:25 pm
SXM
- MDW
1 stop11h 15m
Southwest
Deal found 4/4![Southwest logo]()
$645
This Southwest deal was found by Cheapflights users on 4/5. 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.
Fri 7/315:10 am
MDW
- SXM
1 stop7h 15m
Southwest
Mon 8/32:25 pm
SXM
- MDW
1 stop7h 55m
Southwest
Deal found 4/5![Southwest logo]()
$665
This Southwest deal was found by Cheapflights users on 4/2. 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 6/128:50 pm
MDW
- SXM
2 stops17h 15m
Southwest
Tue 6/163:00 pm
SXM
- MDW
1 stop8h 00m
Southwest
Deal found 4/2![Southwest logo]()
$675
Last-minute flights from Chicago to St. MaartenDiscover last-minute flight deals from Chicago to St. Maarten. Data last updated April 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to St. Maarten. Data last updated April 7, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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.
Sat 4/187:15 pm
ORD
- SXM
1 stop17h 22m
Spirit Airlines
Sat 4/252:42 pm
SXM
- ORD
1 stop10h 42m
Spirit Airlines
Deal found 4/2![Spirit Airlines logo]()
$277
This Expedia deal was found by Cheapflights users on 4/7. 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 4/188:40 am
ORD
- SXM
2 stops53h 15m
Multiple Airlines
Sat 4/252:42 pm
SXM
- ORD
1 stop10h 42m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$317
This Cheapflightsfares deal was found by Cheapflights users on 4/5. 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.
Sun 4/195:05 am
ORD
- SXM
1 stop7h 32m
Spirit Airlines
Thu 4/232:42 pm
SXM
- ORD
1 stop10h 42m
Spirit Airlines
Deal found 4/5![Spirit Airlines logo]()
$254
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:15 pm
ORD
- SXM
1 stop17h 22m
Spirit Airlines
Thu 4/302:42 pm
SXM
- ORD
1 stop19h 54m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$301
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:21 pm
ORD
- SXM
2 stops19h 34m
Multiple Airlines
Thu 4/302:42 pm
SXM
- ORD
1 stop10h 42m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 4/2. 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 5/25:15 am
MDW
- SXM
1 stop7h 25m
Southwest
Thu 5/72:25 pm
SXM
- MDW
1 stop10h 50m
Southwest
Deal found 4/2![Southwest logo]()
$622
This Priceline deal was found by Cheapflights users on 4/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:05 am
ORD
- SXM
1 stop7h 32m
Spirit Airlines
Thu 5/72:35 pm
SXM
- ORD
1 stop9h 40m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$278
This Southwest deal was found by Cheapflights users on 4/2. 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 5/35:05 am
MDW
- SXM
1 stop8h 20m
Southwest
Fri 5/292:25 pm
SXM
- MDW
1 stop10h 50m
Southwest
Deal found 4/2![Southwest logo]()
$570
This Southwest deal was found by Cheapflights users on 4/5. 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.
Sun 5/35:05 am
MDW
- SXM
1 stop8h 20m
Southwest
Sat 5/91:20 pm
SXM
- MDW
1 stop10h 15m
Southwest
Deal found 4/5![Southwest logo]()
$615
This Southwest deal was found by Cheapflights users on 4/5. 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.
Tue 5/58:50 pm
MDW
- SXM
2 stops15h 40m
Southwest
Tue 5/122:25 pm
SXM
- MDW
2 stops18h 10m
Southwest
Deal found 4/5![Southwest logo]()
$520
This Southwest deal was found by Cheapflights users on 4/6. 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 5/115:35 am
MDW
- SXM
1 stop6h 55m
Southwest
Mon 5/182:25 pm
SXM
- MDW
1 stop10h 50m
Southwest
Deal found 4/6![Southwest logo]()
$590
This Southwest deal was found by Cheapflights users on 4/5. 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.
Wed 5/136:00 am
MDW
- SXM
1 stop6h 30m
Southwest
Wed 5/202:25 pm
SXM
- MDW
2 stops17h 45m
Southwest
Deal found 4/5![Southwest logo]()
$620
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 April 7, 2026.
Search for one-way flight options from Chicago to St. Maarten. Find affordable one-way fares based on user searches. Data last updated April 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:05 am
ORD
- SXM
1 stop7h 32m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:05 pm
ORD
- SXM
1 stop20h 25m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$131
This Expedia deal was found by Cheapflights users on 4/3. 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 6/38:20 pm
ORD
- SXM
1 stop19h 40m
Air Canada
Deal found 4/3![Air Canada logo]()
$133
This Gotogate deal was found by Cheapflights users on 4/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/171:55 pm
ORD
- SXM
2 stops22h 40m
Air Canada
Deal found 4/6![Air Canada logo]()
$146
This Super.com deal was found by Cheapflights users on 4/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/297:15 pm
ORD
- SXM
1 stop17h 22m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$151
This CheapOair deal was found by Cheapflights users on 4/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:15 pm
ORD
- SXM
1 stop17h 22m
Spirit Airlines
Deal found 4/2![Spirit Airlines logo]()
$155
This Air Canada deal was found by Cheapflights users on 4/6. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:55 pm
ORD
- SXM
1 stop27h 05m
Air Canada
Deal found 4/6![Air Canada logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:15 pm
ORD
- SXM
1 stop17h 22m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:05 pm
ORD
- SXM
1 stop20h 25m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:10 am
MDW
- SXM
2 stops30h 27m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 4/3. 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.
Mon 4/275:35 am
MDW
- SXM
1 stop6h 55m
Southwest
Deal found 4/3![Southwest logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:24 pm
MDW
- SXM
3 stops19h 06m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$249
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 April 7, 2026.
Round-trip from | $254 (Cheapflightsfares) |
|---|---|
One-way from | $100 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $787 |
Good round-trip deal | $737 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 April 7, 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 - SXM
ORDSXM
Chicago O'Hare Intl
Sat 6/13
7:09 am-5:00 pm
1 stop8h 51m
Simpson Bay Princess Juliana
Sat 6/20
6:00 pm-1:22 pm
1 stop20h 22m
$359
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 6/6
5:05 am-1:30 pm
1 stop7h 25m
Simpson Bay Princess Juliana
Sat 6/13
6:00 pm-7:45 am
2 stops14h 45m
$459
Quickest round-trip
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Tue 5/5
5:55 am-1:30 pm
1 stop6h 35m
Simpson Bay Princess Juliana
Tue 5/12
2:25 pm-9:55 pm
1 stop8h 30m
$515
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 4/18
8:31 am-12:35 pm
1 stop27h 04m
Simpson Bay Princess Juliana
Sat 4/25
12:30 pm-7:41 am
1 stop20h 11m
$527
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Sun 5/3
5:05 am-2:25 pm
1 stop8h 20m
Simpson Bay Princess Juliana
Fri 5/29
2:25 pm-12:15 am
1 stop10h 50m
$570
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Sun 5/3
8:55 pm-1:30 pm
2 stops15h 35m
Simpson Bay Princess Juliana
Thu 5/28
2:25 pm-12:15 am
1 stop10h 50m
$575
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Mon 5/11
5:35 am-1:30 pm
1 stop6h 55m
Simpson Bay Princess Juliana
Mon 5/18
2:25 pm-12:15 am
1 stop10h 50m
$590
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Tue 5/26
5:55 am-1:30 pm
1 stop6h 35m
Simpson Bay Princess Juliana
Tue 6/2
2:25 pm-9:55 pm
1 stop8h 30m
$625
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Sun 7/5
5:20 am-3:30 pm
1 stop9h 10m
Simpson Bay Princess Juliana
Fri 7/10
2:25 pm-12:40 am
1 stop11h 15m
$645
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Tue 5/5
5:15 am-2:05 pm
1 stop7h 50m
Simpson Bay Princess Juliana
Tue 5/12
3:20 pm-10:27 pm
1 stop8h 07m
$665
Showing 1-10 of 34 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 $231). Flying from Chicago to St. Maarten in April is currently the most expensive (average of $630). 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 April 7, 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 114 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 20% of flights being delayed.
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 April 7, 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.
Food
7.2
Comfort
7.9
Crew
8.5
Entertainment
7.8
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Comfort
7.9
Crew
8.5
Entertainment
7.8
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Comfort
7.9
Crew
8.5
Entertainment
7.8
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Comfort
7.9
Crew
8.5
Entertainment
7.8
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Comfort
7.9
Crew
8.5
Entertainment
7.8
Boarding
8.1
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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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Chicago and St. Maarten flights
Browse other Chicago and St. Maarten flight options. Last updated on April 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to St. Maarten
Discover the top 6 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 April 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$231 | Average$421 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$240 | Average$510 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$389 | Average$730 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$487 | Average$617 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$501 | Average$719 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$731 | FlexibilityNo cancel fee | On-time62% |