$94+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Apr 9 — Apr 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 March 10, 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 March 10, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Thu 4/232:42 pm
SXM
- ORD
1 stop10h 42m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$329
This Booking.com deal was found by Cheapflights users on 3/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:15 pm
ORD
- SXM
1 stop17h 22m
Spirit Airlines
Sat 5/92:42 pm
SXM
- ORD
1 stop10h 42m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$333
This CheapOair deal was found by Cheapflights users on 3/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/75:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Tue 4/142:35 pm
SXM
- ORD
1 stop20h 01m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/75:05 am
ORD
- SXM
1 stop7h 25m
Multiple Airlines
Tue 4/142:35 pm
SXM
- ORD
1 stop31h 42m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$335
This Cheapflightsfares deal was found by Cheapflights users on 3/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:05 am
ORD
- SXM
1 stop7h 32m
Spirit Airlines
Thu 4/232:42 pm
SXM
- ORD
1 stop10h 42m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$339
This Priceline deal was found by Cheapflights users on 3/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Thu 4/162:42 pm
SXM
- ORD
1 stop10h 42m
Spirit Airlines
Deal found 3/7![Spirit Airlines logo]()
$340
This CheapOair deal was found by Cheapflights users on 3/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/25:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Tue 4/72:35 pm
SXM
- ORD
2 stops19h 15m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$342
This Cheapflightsfares deal was found by Cheapflights users on 3/7. 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 4/25:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Wed 4/82:35 pm
SXM
- ORD
1 stop9h 42m
Spirit Airlines
Deal found 3/7![Spirit Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 3/8. 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.
Tue 4/78:50 pm
MDW
- SXM
2 stops15h 40m
Southwest
Tue 4/142:25 pm
SXM
- MDW
2 stops18h 10m
Southwest
Deal found 3/8![Southwest logo]()
$506
This Southwest deal was found by Cheapflights users on 3/8. 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.
Tue 5/56:00 am
MDW
- SXM
1 stop6h 30m
Southwest
Sat 5/91:20 pm
SXM
- MDW
1 stop10h 15m
Southwest
Deal found 3/8![Southwest logo]()
$573
This Southwest deal was found by Cheapflights users on 3/5. 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 4/245:35 am
MDW
- SXM
1 stop6h 55m
Southwest
Thu 4/302:25 pm
SXM
- MDW
1 stop10h 40m
Southwest
Deal found 3/5![Southwest logo]()
$581
This Southwest deal was found by Cheapflights users on 3/5. 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.
Sat 4/255:15 am
MDW
- SXM
1 stop7h 25m
Southwest
Fri 5/12:25 pm
SXM
- MDW
2 stops18h 30m
Southwest
Deal found 3/5![Southwest logo]()
$586
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 March 10, 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 March 10, 2026.
This Mytrip deal was found by Cheapflights users on 3/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/25:05 am
ORD
- SXM
1 stop7h 25m
Multiple Airlines
Sun 4/52:35 pm
SXM
- ORD
3 stops23h 35m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$510
This Southwest deal was found by Cheapflights users on 3/7. 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.
Tue 5/125:55 am
ORD
- SXM
1 stop6h 35m
Southwest
Tue 5/192:25 pm
SXM
- ORD
1 stop8h 30m
Southwest
Deal found 3/7![Southwest logo]()
$543
This Delta deal was found by Cheapflights users on 3/6. 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.
Fri 5/86:00 am
ORD
- SXM
1 stop6h 55m
Delta
Wed 5/133:20 pm
SXM
- ORD
1 stop9h 39m
Delta
Deal found 3/6![Delta logo]()
$670
This Southwest deal was found by Cheapflights users on 3/8. 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.
Wed 4/225:55 am
ORD
- SXM
1 stop6h 35m
Southwest
Wed 4/292:25 pm
SXM
- ORD
1 stop8h 30m
Southwest
Deal found 3/8![Southwest logo]()
$553
This Southwest deal was found by Cheapflights users on 3/5. 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.
Sat 4/255:15 am
MDW
- SXM
1 stop7h 25m
Southwest
Fri 5/12:25 pm
SXM
- MDW
2 stops18h 30m
Southwest
Deal found 3/5![Southwest logo]()
$586
This Southwest deal was found by Cheapflights users on 3/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:15 pm
ORD
- SXM
2 stops17h 45m
Southwest
Tue 6/93:00 pm
SXM
- ORD
1 stop9h 55m
Southwest
Deal found 3/9![Southwest logo]()
$610
This Delta deal was found by Cheapflights users on 3/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:20 pm
MDW
- SXM
1 stop17h 00m
Delta
Tue 4/73:20 pm
SXM
- MDW
2 stops27h 34m
Delta
Deal found 3/7![Delta logo]()
$805
This Southwest deal was found by Cheapflights users on 3/6. 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.
Wed 5/65:35 pm
MDW
- SXM
2 stops18h 55m
Southwest
Sat 5/91:20 pm
SXM
- MDW
1 stop10h 15m
Southwest
Deal found 3/6![Southwest logo]()
$620
This Delta deal was found by Cheapflights users on 3/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:20 pm
MDW
- SXM
1 stop17h 00m
Delta
Wed 4/83:20 pm
SXM
- MDW
2 stops27h 34m
Delta
Deal found 3/7![Delta logo]()
$805
This Southwest deal was found by Cheapflights users on 3/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/196:00 am
ORD
- SXM
1 stop7h 35m
Southwest
Sun 7/262:15 pm
SXM
- ORD
1 stop9h 20m
Southwest
Deal found 3/9![Southwest logo]()
$625
This Southwest deal was found by Cheapflights users on 3/7. 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.
Sun 6/146:00 am
ORD
- SXM
1 stop7h 35m
Southwest
Sun 6/212:15 pm
SXM
- ORD
1 stop9h 20m
Southwest
Deal found 3/7![Southwest logo]()
$625
This Southwest deal was found by Cheapflights users on 3/8. 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 5/85:35 am
MDW
- SXM
1 stop6h 55m
Southwest
Wed 5/132:25 pm
SXM
- MDW
2 stops17h 45m
Southwest
Deal found 3/8![Southwest logo]()
$630
This Southwest deal was found by Cheapflights users on 3/6. 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.
Wed 5/66:00 am
MDW
- SXM
1 stop6h 30m
Southwest
Sun 5/103:20 pm
SXM
- MDW
1 stop9h 20m
Southwest
Deal found 3/6![Southwest logo]()
$645
This Southwest deal was found by Cheapflights users on 3/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
ORD
- SXM
1 stop8h 05m
Southwest
Sat 7/112:25 pm
SXM
- ORD
1 stop10h 30m
Southwest
Deal found 3/9![Southwest logo]()
$645
This Southwest deal was found by Cheapflights users on 3/7. 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 6/155:10 pm
ORD
- SXM
2 stops19h 50m
Southwest
Mon 6/223:00 pm
SXM
- ORD
1 stop9h 55m
Southwest
Deal found 3/7![Southwest logo]()
$650
This Southwest deal was found by Cheapflights users on 3/7. 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.
Tue 6/165:55 pm
ORD
- SXM
2 stops19h 05m
Southwest
Mon 6/223:00 pm
SXM
- ORD
1 stop9h 55m
Southwest
Deal found 3/7![Southwest logo]()
$650
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 6/228:05 pm
ORD
- SXM
2 stops16h 55m
Southwest
Mon 6/293:00 pm
SXM
- ORD
1 stop9h 55m
Southwest
Deal found 3/10![Southwest logo]()
$650
This Southwest deal was found by Cheapflights users on 3/6. 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.
Sat 5/25:15 am
MDW
- SXM
1 stop7h 25m
Southwest
Sat 5/91:20 pm
SXM
- MDW
1 stop10h 15m
Southwest
Deal found 3/6![Southwest logo]()
$670
This Southwest deal was found by Cheapflights users on 3/6. 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.
Sat 6/68:10 pm
MDW
- SXM
2 stops17h 25m
Southwest
Sat 6/132:25 pm
SXM
- MDW
2 stops17h 45m
Southwest
Deal found 3/6![Southwest logo]()
$700
This Southwest deal was found by Cheapflights users on 3/5. 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 4/156:00 am
MDW
- SXM
1 stop6h 30m
Southwest
Mon 4/202:25 pm
SXM
- MDW
1 stop10h 40m
Southwest
Deal found 3/5![Southwest logo]()
$735
This Southwest deal was found by Cheapflights users on 3/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:15 pm
MDW
- SXM
2 stops15h 15m
Southwest
Mon 4/202:25 pm
SXM
- MDW
1 stop10h 40m
Southwest
Deal found 3/9![Southwest logo]()
$740
Last-minute flights from Chicago to St. MaartenDiscover last-minute flight deals from Chicago to St. Maarten. Data last updated March 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to St. Maarten. Data last updated March 10, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 3/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/25:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Tue 4/72:35 pm
SXM
- ORD
2 stops19h 15m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$342
This Cheapflightsfares deal was found by Cheapflights users on 3/7. 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 4/25:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Wed 4/82:35 pm
SXM
- ORD
1 stop9h 42m
Spirit Airlines
Deal found 3/7![Spirit Airlines logo]()
$344
This CheapOair deal was found by Cheapflights users on 3/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/75:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Tue 4/142:35 pm
SXM
- ORD
1 stop20h 01m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/75:05 am
ORD
- SXM
1 stop7h 25m
Multiple Airlines
Tue 4/142:35 pm
SXM
- ORD
1 stop31h 42m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 3/8. 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.
Tue 4/78:50 pm
MDW
- SXM
2 stops15h 40m
Southwest
Tue 4/142:25 pm
SXM
- MDW
2 stops18h 10m
Southwest
Deal found 3/8![Southwest logo]()
$506
This Priceline deal was found by Cheapflights users on 3/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Thu 4/162:42 pm
SXM
- ORD
1 stop10h 42m
Spirit Airlines
Deal found 3/7![Spirit Airlines logo]()
$340
This Cheapflightsfares deal was found by Cheapflights users on 3/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Sat 4/182:42 pm
SXM
- ORD
1 stop10h 42m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$349
This Cheapflightsfares deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Thu 4/232:42 pm
SXM
- ORD
1 stop10h 42m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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.
Mon 4/135:05 am
ORD
- SXM
1 stop7h 25m
Multiple Airlines
Thu 4/2312:25 pm
SXM
- ORD
2 stops25h 40m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$356
This Cheapflightsfares deal was found by Cheapflights users on 3/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:05 am
ORD
- SXM
1 stop7h 32m
Spirit Airlines
Thu 4/232:42 pm
SXM
- ORD
1 stop10h 42m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 3/5. 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 4/245:35 am
MDW
- SXM
1 stop6h 55m
Southwest
Thu 4/302:25 pm
SXM
- MDW
1 stop10h 40m
Southwest
Deal found 3/5![Southwest logo]()
$581
This Southwest deal was found by Cheapflights users on 3/5. 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.
Sat 4/255:15 am
MDW
- SXM
1 stop7h 25m
Southwest
Fri 5/12:25 pm
SXM
- MDW
2 stops18h 30m
Southwest
Deal found 3/5![Southwest logo]()
$586
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 March 10, 2026.
Search for one-way flight options from Chicago to St. Maarten. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
This Priceline deal was found by Cheapflights users on 3/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/25:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Deal found 3/7![Spirit Airlines logo]()
$94
This Super.com deal was found by Cheapflights users on 3/9. 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.
Wed 4/85:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 3/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/65:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 3/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/55:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 3/6. 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.
Tue 4/75:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com 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
Deal found 3/5![Spirit Airlines logo]()
$118
This Trip.com deal was found by Cheapflights users on 3/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/36:10 pm
ORD
- SXM
1 stop18h 20m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:10 pm
ORD
- SXM
1 stop18h 20m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$128
This Priceline deal was found by Cheapflights users on 3/9. 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 Priceline 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
Deal found 3/9![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:25 pm
MDW
- SXM
2 stops18h 05m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:30 am
MDW
- SXM
2 stops24h 00m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$154
This Priceline deal was found by Cheapflights users on 3/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/32:56 pm
MDW
- SXM
1 stop23h 19m
Frontier
Deal found 3/9![Frontier logo]()
$156
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 March 10, 2026.
Round-trip from | $330 (Priceline) |
|---|---|
One-way from | $94 (Priceline) |
Popular in | December |
Cheapest in | September |
Average price | $607 |
Good round-trip deal | $891 or less |
Good one-way deal | $304 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 March 10, 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
Thu 4/2
5:05 am-1:30 pm
1 stop7h 25m
Simpson Bay Princess Juliana
Sun 4/5
2:35 pm-1:10 pm
3 stops23h 35m
$510
Quickest round-trip
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Tue 5/12
5:55 am-1:30 pm
1 stop6h 35m
Simpson Bay Princess Juliana
Tue 5/19
2:25 pm-9:55 pm
1 stop8h 30m
$543
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Wed 4/22
5:55 am-1:30 pm
1 stop6h 35m
Simpson Bay Princess Juliana
Wed 4/29
2:25 pm-9:55 pm
1 stop8h 30m
$553
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Sat 4/25
5:15 am-1:40 pm
1 stop7h 25m
Simpson Bay Princess Juliana
Fri 5/1
2:25 pm-7:55 am
2 stops18h 30m
$586
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Wed 6/3
7:15 pm-2:00 pm
2 stops17h 45m
Simpson Bay Princess Juliana
Tue 6/9
3:00 pm-11:55 pm
1 stop9h 55m
$610
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Wed 5/6
5:35 pm-1:30 pm
2 stops18h 55m
Simpson Bay Princess Juliana
Sat 5/9
1:20 pm-10:35 pm
1 stop10h 15m
$620
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sun 7/19
6:00 am-2:35 pm
1 stop7h 35m
Simpson Bay Princess Juliana
Sun 7/26
2:15 pm-10:35 pm
1 stop9h 20m
$625
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sun 6/14
6:00 am-2:35 pm
1 stop7h 35m
Simpson Bay Princess Juliana
Sun 6/21
2:15 pm-10:35 pm
1 stop9h 20m
$625
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 5/8
5:35 am-1:30 pm
1 stop6h 55m
Simpson Bay Princess Juliana
Wed 5/13
2:25 pm-7:10 am
2 stops17h 45m
$630
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Wed 5/6
6:00 am-1:30 pm
1 stop6h 30m
Simpson Bay Princess Juliana
Sun 5/10
3:20 pm-11:40 pm
1 stop9h 20m
$645
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.
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 June is currently the most expensive (average of $593). 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 March 10, 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 26% of weekly flights between Chicago and St. Maarten have experienced delays in the past year, with the average delay time being 94 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 March 10, 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
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Crew
8.5
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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Alternative routes for Chicago to St. Maarten
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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 March 10, 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 March 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$231 | Average$389 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$290 | Average$515 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$389 | Average$746 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$487 | Average$617 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$501 | Average$695 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$568 | Average$731 | FlexibilityNo cancel fee | On-time62% |