$116+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Aug 7 — Aug 141
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to St. Maarten with Cheapflights
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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 July 8, 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 July 8, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 7/3. 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 Cheapflightsfares 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 7/3![JetBlue logo]()
$317
This Southwest deal was found by Cheapflights users on 7/4. 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
Thu 9/33:05 pm
SXM
- MDW
1 stop8h 35m
Southwest
Deal found 7/4![Southwest logo]()
$325
This Cheapflightsfares deal was found by Cheapflights users on 7/4. 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.
Thu 9/106:00 am
ORD
- SXM
1 stop7h 00m
JetBlue
Mon 9/143:05 pm
SXM
- ORD
1 stop9h 26m
JetBlue
Deal found 7/4![JetBlue logo]()
$377
This Southwest deal was found by Cheapflights users on 7/7. 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.
Fri 8/215:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Fri 8/283:05 pm
SXM
- MDW
1 stop8h 35m
Southwest
Deal found 7/7![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Fri 8/213:05 pm
SXM
- MDW
1 stop8h 35m
Southwest
Deal found 7/3![Southwest logo]()
$385
This Cheapflightsfares deal was found by Cheapflights users on 7/7. 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 9/176:00 am
ORD
- SXM
1 stop7h 00m
JetBlue
Sun 9/203:05 pm
SXM
- ORD
1 stop9h 26m
JetBlue
Deal found 7/7![JetBlue logo]()
$388
This Despegar deal was found by Cheapflights users on 7/7. 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 Despegar 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 19m
JetBlue
Fri 8/281:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 7/7![JetBlue logo]()
$406
This Expedia deal was found by Cheapflights users on 7/7. 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 8/218:20 pm
ORD
- SXM
1 stop14h 13m
JetBlue
Fri 8/281:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 7/7![JetBlue logo]()
$414
This Priceline deal was found by Cheapflights users on 7/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am
ORD
- SXM
1 stop7h 00m
Multiple Airlines
Sat 9/266:00 pm
SXM
- ORD
2 stops14h 44m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$415
This Priceline deal was found by Cheapflights users on 7/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:21 pm
ORD
- SXM
2 stops21h 39m
Multiple Airlines
Fri 9/253:05 pm
SXM
- ORD
1 stop9h 26m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$420
This FlightHub deal was found by Cheapflights users on 7/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:00 am
ORD
- SXM
1 stop7h 00m
JetBlue
Mon 9/213:05 pm
SXM
- ORD
1 stop9h 26m
JetBlue
Deal found 7/6![JetBlue logo]()
$421
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Fri 9/253:05 pm
SXM
- MDW
1 stop8h 35m
Southwest
Deal found 7/3![Southwest logo]()
$445
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 July 8, 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 July 8, 2026.
This Southwest deal was found by Cheapflights users on 7/7. 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.
Fri 8/215:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Fri 8/283:05 pm
SXM
- MDW
1 stop8h 35m
Southwest
Deal found 7/7![Southwest logo]()
$383
This JetBlue deal was found by Cheapflights users on 7/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:20 pm
ORD
- SXM
1 stop14h 13m
JetBlue
Fri 8/281:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 7/7![JetBlue logo]()
$422
This CheapOair deal was found by Cheapflights users on 7/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:21 pm
ORD
- SXM
2 stops19h 24m
Air Canada
Sat 10/312:40 pm
SXM
- ORD
2 stops26h 58m
Air Canada
Deal found 7/3![Air Canada logo]()
$536
This American Airlines deal was found by Cheapflights users on 7/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:53 pm
ORD
- SXM
2 stops15h 29m
American Airlines
Fri 8/282:42 pm
SXM
- ORD
2 stops10h 17m
American Airlines
Deal found 7/7![American Airlines logo]()
$670
This United Airlines deal was found by Cheapflights users on 7/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 pm
ORD
- SXM
1 stop17h 50m
United Airlines
Sat 10/311:10 pm
SXM
- ORD
Nonstop6h 01m
United Airlines
Deal found 7/4![United Airlines logo]()
$695
This Southwest deal was found by Cheapflights users on 7/4. 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 8/287:55 pm
MDW
- SXM
2 stops16h 00m
Southwest
Thu 9/33:05 pm
SXM
- MDW
1 stop8h 35m
Southwest
Deal found 7/4![Southwest logo]()
$390
This Southwest deal was found by Cheapflights users on 7/4. 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 10/125:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Thu 10/153:05 pm
SXM
- MDW
1 stop10h 15m
Southwest
Deal found 7/4![Southwest logo]()
$448
This JetBlue deal was found by Cheapflights users on 7/4. 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.
Tue 8/186:30 pm
ORD
- SXM
1 stop14h 34m
JetBlue
Tue 8/251:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 7/4![JetBlue logo]()
$537
This Southwest deal was found by Cheapflights users on 7/5. 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 11/108:50 pm
MDW
- SXM
2 stops15h 30m
Southwest
Tue 11/243:20 pm
SXM
- MDW
2 stops10h 50m
Southwest
Deal found 7/5![Southwest logo]()
$456
This JetBlue deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:27 pm
ORD
- SXM
1 stop15h 37m
JetBlue
Wed 9/21:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 7/3![JetBlue logo]()
$544
This Southwest deal was found by Cheapflights users on 7/4. 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 8/145:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Fri 8/213:05 pm
SXM
- MDW
1 stop8h 35m
Southwest
Deal found 7/4![Southwest logo]()
$475
This JetBlue deal was found by Cheapflights users on 7/5. 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 7/255:27 pm
ORD
- SXM
1 stop15h 35m
JetBlue
Thu 7/301:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 7/5![JetBlue logo]()
$554
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:05 am
MDW
- SXM
1 stop7h 15m
Southwest
Tue 11/173:20 pm
SXM
- MDW
2 stops16h 20m
Southwest
Deal found 7/3![Southwest logo]()
$483
This Southwest deal was found by Cheapflights users on 7/7. 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 8/225:00 am
MDW
- SXM
1 stop6h 55m
Southwest
Fri 8/283:05 pm
SXM
- MDW
1 stop8h 35m
Southwest
Deal found 7/7![Southwest logo]()
$506
This United Airlines deal was found by Cheapflights users on 7/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/319:35 pm
ORD
- SXM
1 stop15h 15m
United Airlines
Sat 11/72:10 pm
SXM
- ORD
Nonstop6h 01m
United Airlines
Deal found 7/4![United Airlines logo]()
$815
This Southwest deal was found by Cheapflights users on 7/6. 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.
Thu 11/125:05 am
MDW
- SXM
1 stop7h 15m
Southwest
Mon 11/163:20 pm
SXM
- MDW
2 stops22h 45m
Southwest
Deal found 7/6![Southwest logo]()
$510
Last-minute flights from Chicago to St. MaartenDiscover last-minute flight deals from Chicago to St. Maarten. Data last updated July 8, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to St. Maarten. Data last updated July 8, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Fri 8/213:05 pm
SXM
- MDW
1 stop8h 35m
Southwest
Deal found 7/3![Southwest logo]()
$385
This Priceline deal was found by Cheapflights users on 7/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:13 pm
ORD
- SXM
1 stop17h 17m
Multiple Airlines
Fri 8/211:42 pm
SXM
- ORD
1 stop11h 02m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$465
This Despegar deal was found by Cheapflights users on 7/4. 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 Despegar is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:27 pm
ORD
- SXM
1 stop21h 52m
JetBlue
Fri 8/211:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 7/4![JetBlue logo]()
$475
This Cheapflightsfares deal was found by Cheapflights users on 7/5. 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 8/156:00 am
ORD
- SXM
1 stop9h 19m
JetBlue
Sat 8/221:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 7/5![JetBlue logo]()
$459
This Justfly.com deal was found by Cheapflights users on 7/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:00 am
ORD
- SXM
1 stop28h 37m
JetBlue
Sat 8/221:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 7/3![JetBlue logo]()
$447
This Southwest deal was found by Cheapflights users on 7/3. 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 8/175:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Mon 8/243:05 pm
SXM
- MDW
1 stop8h 35m
Southwest
Deal found 7/3![Southwest logo]()
$571
This JetBlue deal was found by Cheapflights users on 7/5. 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.
Wed 8/196:30 pm
ORD
- SXM
1 stop14h 34m
JetBlue
Wed 8/261:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 7/5![JetBlue logo]()
$434
This Southwest deal was found by Cheapflights users on 7/7. 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.
Fri 8/215:00 am
MDW
- SXM
1 stop8h 05m
Southwest
Fri 8/283:05 pm
SXM
- MDW
1 stop8h 35m
Southwest
Deal found 7/7![Southwest logo]()
$383
This Expedia deal was found by Cheapflights users on 7/7. 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 8/218:20 pm
ORD
- SXM
1 stop14h 13m
JetBlue
Fri 8/281:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 7/7![JetBlue logo]()
$414
This Despegar deal was found by Cheapflights users on 7/7. 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 Despegar 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 19m
JetBlue
Fri 8/281:42 pm
SXM
- ORD
1 stop11h 02m
JetBlue
Deal found 7/7![JetBlue logo]()
$406
This Southwest deal was found by Cheapflights users on 7/6. 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 8/226:00 pm
MDW
- SXM
2 stops19h 05m
Southwest
Fri 8/283:05 pm
SXM
- MDW
2 stops17h 30m
Southwest
Deal found 7/6![Southwest logo]()
$450
This Southwest deal was found by Cheapflights users on 7/4. 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
Thu 9/33:05 pm
SXM
- MDW
1 stop8h 35m
Southwest
Deal found 7/4![Southwest logo]()
$325
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 July 8, 2026.
Search for one-way flight options from Chicago to St. Maarten. Find affordable one-way fares based on user searches. Data last updated July 8, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 7/6. 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 10/46:00 am
ORD
- SXM
1 stop7h 00m
JetBlue
Deal found 7/6![JetBlue logo]()
$116
This Cheapflightsfares deal was found by Cheapflights users on 7/4. 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.
Fri 10/26:00 am
ORD
- SXM
1 stop7h 00m
JetBlue
Deal found 7/4![JetBlue logo]()
$117
This Southwest deal was found by Cheapflights users on 7/4. 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 8/235:10 am
MDW
- SXM
1 stop7h 55m
Southwest
Deal found 7/4![Southwest logo]()
$118
This Justfly.com deal was found by Cheapflights users on 7/4. 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.
Thu 10/16:00 am
ORD
- SXM
1 stop7h 00m
JetBlue
Deal found 7/4![JetBlue logo]()
$151
This Southwest deal was found by Cheapflights users on 7/7. 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 11/105:15 am
MDW
- SXM
1 stop7h 05m
Southwest
Deal found 7/7![Southwest logo]()
$176
This Southwest deal was found by Cheapflights users on 7/5. 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 8/148:15 pm
MDW
- SXM
2 stops15h 40m
Southwest
Deal found 7/5![Southwest logo]()
$178
This Priceline deal was found by Cheapflights users on 7/6. 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.
Fri 8/145:13 pm
ORD
- SXM
1 stop17h 17m
Frontier
Deal found 7/6![Frontier logo]()
$198
This Priceline deal was found by Cheapflights users on 7/7. 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 8/136:00 am
ORD
- SXM
1 stop27h 04m
JetBlue
Deal found 7/7![JetBlue logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 7/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:30 pm
ORD
- SXM
1 stop14h 34m
JetBlue
Deal found 7/3![JetBlue logo]()
$209
This Air Canada deal was found by Cheapflights users on 7/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:09 am
ORD
- SXM
1 stop8h 51m
Air Canada
Deal found 7/3![Air Canada logo]()
$214
This Air Canada deal was found by Cheapflights users on 7/7. 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.
Wed 10/76:21 pm
ORD
- SXM
2 stops21h 39m
Air Canada
Deal found 7/7![Air Canada logo]()
$215
This JetBlue deal was found by Cheapflights users on 7/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:30 pm
ORD
- SXM
1 stop14h 34m
JetBlue
Deal found 7/6![JetBlue logo]()
$217
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 July 8, 2026.
Round-trip from | $317 (Cheapflightsfares) |
|---|---|
One-way from | $116 (Cheapflightsfares) |
Popular in | June |
Cheapest in | January |
Average price | $722 |
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 July 8, 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
Fri 8/21
5:00 am-2:05 pm
1 stop8h 05m
Simpson Bay Princess Juliana
Fri 8/28
3:05 pm-10:40 pm
1 stop8h 35m
$383
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 8/28
7:55 pm-12:55 pm
2 stops16h 00m
Simpson Bay Princess Juliana
Thu 9/3
3:05 pm-10:40 pm
1 stop8h 35m
$390
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Fri 8/21
8:20 pm-11:33 am
1 stop14h 13m
Simpson Bay Princess Juliana
Fri 8/28
1:42 pm-11:44 pm
1 stop11h 02m
$422
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Mon 10/12
5:00 am-2:05 pm
1 stop8h 05m
Simpson Bay Princess Juliana
Thu 10/15
3:05 pm-12:20 am
1 stop10h 15m
$448
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Tue 11/10
8:50 pm-2:20 pm
2 stops15h 30m
Simpson Bay Princess Juliana
Tue 11/24
3:20 pm-12:10 am
2 stops10h 50m
$456
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 8/14
5:00 am-2:05 pm
1 stop8h 05m
Simpson Bay Princess Juliana
Fri 8/21
3:05 pm-10:40 pm
1 stop8h 35m
$475
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Fri 11/13
5:05 am-2:20 pm
1 stop7h 15m
Simpson Bay Princess Juliana
Tue 11/17
3:20 pm-5:40 am
2 stops16h 20m
$483
Quickest round-trip
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Sat 8/22
5:00 am-12:55 pm
1 stop6h 55m
Simpson Bay Princess Juliana
Fri 8/28
3:05 pm-10:40 pm
1 stop8h 35m
$506
ChicagoSimpson Bay
MDW - SXM
MDWSXM
Chicago Midway
Thu 11/12
5:05 am-2:20 pm
1 stop7h 15m
Simpson Bay Princess Juliana
Mon 11/16
3:20 pm-12:05 pm
2 stops22h 45m
$510
ChicagoSimpson Bay
ORD - SXM
ORDSXM
Chicago O'Hare Intl
Sat 10/24
6:21 pm-2:45 pm
2 stops19h 24m
Simpson Bay Princess Juliana
Sat 10/31
2:40 pm-4:38 pm
2 stops26h 58m
$536
Showing 1-10 of 33 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 52 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Reviews of airlines servicing St. Maarten
Get insights into the airlines that provide service to St. Maarten. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to St. Maarten. Reviews last updated July 8, 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
Crew
8.5
Entertainment
7.8
Overall
7.8
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Entertainment
7.8
Overall
7.8
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Entertainment
7.8
Overall
7.8
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Entertainment
7.8
Overall
7.8
Boarding
8.1
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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Chicago and St. Maarten flights
Browse other Chicago and St. Maarten flight options. Last updated on July 8, 2026.
Popular flight searches
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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 July 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$240 | Average$392 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$389 | Average$711 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$389 | Average$756 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$487 | Average$617 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$500 | Average$738 | FlexibilityNo cancel fee | On-time71% |