$149+ Cheap flights from St. Maarten to Chicago (CHI)
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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
mar 4 — mar 111
1 adult, Economy
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Find cheap flights from St. Maarten to Chicago 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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from St. Maarten to Chicago
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Cheapest flights from St. Maarten to ChicagoExplore the most affordable flight options available from St. Maarten to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on fevereiro 2, 2026.
Explore the most affordable flight options available from St. Maarten to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on fevereiro 2, 2026.
This Orbitz deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 2/183:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
qui 2/265:15 am
ORD
- SXM
1 stop7h 00m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$251
This Cheapflightsfares deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 2/143:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
sáb 2/215:15 am
ORD
- SXM
1 stop7h 00m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/173:20 pm
SXM
- ORD
1 stop22h 02m
Spirit Airlines
sex 2/278:16 pm
ORD
- SXM
1 stop15h 59m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/173:20 pm
SXM
- ORD
2 stops27h 32m
Multiple Airlines
sex 2/278:16 pm
ORD
- SXM
1 stop15h 59m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$292
This Priceline deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 3/172:20 pm
SXM
- ORD
1 stop9h 57m
Spirit Airlines
ter 3/245:05 am
ORD
- SXM
1 stop7h 10m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 2/73:20 pm
SXM
- ORD
1 stop10h 27m
Multiple Airlines
sáb 2/145:05 am
ORD
- SXM
2 stops31h 10m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 2/73:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
sáb 2/144:43 pm
ORD
- SXM
1 stop19h 32m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/173:20 pm
SXM
- ORD
1 stop22h 02m
Multiple Airlines
qui 2/263:21 pm
ORD
- SXM
1 stop20h 54m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$334
This Cheapflightsfares deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 5/62:11 pm
SXM
- ORD
1 stop10h 30m
Spirit Airlines
dom 5/105:15 am
ORD
- SXM
1 stop7h 01m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$349
This Cheapflightsfares deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 5/72:11 pm
SXM
- ORD
1 stop10h 30m
Spirit Airlines
dom 5/105:15 am
ORD
- SXM
1 stop7h 01m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 2/183:20 pm
SXM
- ORD
2 stops21h 31m
Multiple Airlines
qui 2/268:16 pm
ORD
- SXM
1 stop15h 59m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/171:38 pm
SXM
- MDW
1 stop10h 55m
Delta
sex 2/276:00 am
MDW
- SXM
1 stop6h 50m
Delta
Deal found 1/31![Delta logo]()
$546
Best flights from St. Maarten to ChicagoDiscover carefully curated flight deals from St. Maarten to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated fevereiro 2, 2026.
Discover carefully curated flight deals from St. Maarten to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated fevereiro 2, 2026.
This Orbitz deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 2/183:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
qui 2/265:15 am
ORD
- SXM
1 stop7h 00m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/173:20 pm
SXM
- ORD
2 stops27h 32m
Multiple Airlines
sex 2/278:16 pm
ORD
- SXM
1 stop15h 59m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$292
This Cheapflightsfares deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 2/143:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
sáb 2/215:15 am
ORD
- SXM
1 stop7h 00m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/171:38 pm
SXM
- MDW
1 stop10h 55m
Delta
sex 2/276:00 am
MDW
- SXM
1 stop6h 50m
Delta
Deal found 1/31![Delta logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/173:20 pm
SXM
- ORD
1 stop22h 02m
Spirit Airlines
sex 2/278:16 pm
ORD
- SXM
1 stop15h 59m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/173:20 pm
SXM
- ORD
2 stops21h 19m
Multiple Airlines
qui 2/263:21 pm
ORD
- SXM
1 stop20h 54m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$345
This Priceline deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 3/172:20 pm
SXM
- ORD
1 stop9h 57m
Spirit Airlines
ter 3/245:05 am
ORD
- SXM
1 stop7h 10m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 2/183:20 pm
SXM
- ORD
2 stops21h 31m
Multiple Airlines
qui 2/268:16 pm
ORD
- SXM
1 stop15h 59m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$352
This Cheapflightsfares deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 5/62:11 pm
SXM
- ORD
1 stop10h 30m
Spirit Airlines
dom 5/105:15 am
ORD
- SXM
1 stop7h 01m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$349
This Cheapflightsfares deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 5/72:11 pm
SXM
- ORD
1 stop10h 30m
Spirit Airlines
dom 5/105:15 am
ORD
- SXM
1 stop7h 01m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/171:38 pm
SXM
- MDW
1 stop10h 55m
Delta
qui 2/266:00 am
MDW
- SXM
1 stop6h 50m
Delta
Deal found 1/31![Delta logo]()
$546
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 3/1712:55 pm
SXM
- MDW
1 stop10h 36m
Delta
ter 3/246:00 am
MDW
- SXM
1 stop6h 54m
Delta
Deal found 1/31![Delta logo]()
$562
This Expedia deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 2/163:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
qui 2/265:15 am
ORD
- SXM
1 stop7h 00m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 3/83:20 pm
SXM
- MDW
1 stop19h 45m
Multiple Airlines
dom 3/156:00 am
MDW
- SXM
2 stops27h 50m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$776
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 3/812:55 pm
SXM
- MDW
1 stop22h 01m
Delta
dom 3/156:00 am
MDW
- SXM
1 stop6h 54m
Delta
Deal found 2/1![Delta logo]()
$785
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 2/181:38 pm
SXM
- MDW
1 stop10h 53m
Delta
qui 2/266:00 am
MDW
- SXM
1 stop6h 50m
Delta
Deal found 1/31![Delta logo]()
$1,117
This WestJet deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 3/173:20 pm
SXM
- MDW
2 stops27h 34m
WestJet
ter 3/241:10 pm
MDW
- SXM
2 stops24h 07m
WestJet
Deal found 1/31![WestJet logo]()
$3,189
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 2/161:38 pm
SXM
- MDW
1 stop10h 53m
Delta
qui 2/266:00 am
MDW
- SXM
1 stop6h 50m
Delta
Deal found 1/31![Delta logo]()
$1,353
This WestJet deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/174:20 pm
SXM
- MDW
2 stops52h 20m
WestJet
sex 2/277:20 pm
MDW
- SXM
2 stops41h 57m
WestJet
Deal found 1/31![WestJet logo]()
$3,707
Last-minute flights from St. Maarten to ChicagoDiscover last-minute flight deals from St. Maarten to Chicago. Data last updated fevereiro 2, 2026 and is based on user searches.
Discover last-minute flight deals from St. Maarten to Chicago. Data last updated fevereiro 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 2/73:20 pm
SXM
- ORD
1 stop10h 27m
Multiple Airlines
sáb 2/145:05 am
ORD
- SXM
2 stops31h 10m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 2/73:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
sáb 2/144:43 pm
ORD
- SXM
1 stop19h 32m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$329
This Cheapflightsfares deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 2/143:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
sáb 2/215:15 am
ORD
- SXM
1 stop7h 00m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 2/163:20 pm
SXM
- ORD
2 stops27h 37m
Multiple Airlines
qui 2/263:21 pm
ORD
- SXM
1 stop20h 54m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$415
This Expedia deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 2/163:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
qui 2/265:15 am
ORD
- SXM
1 stop7h 00m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/173:20 pm
SXM
- ORD
1 stop22h 02m
Spirit Airlines
sex 2/278:16 pm
ORD
- SXM
1 stop15h 59m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/173:20 pm
SXM
- ORD
2 stops27h 32m
Multiple Airlines
sex 2/278:16 pm
ORD
- SXM
1 stop15h 59m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/173:20 pm
SXM
- ORD
1 stop22h 02m
Multiple Airlines
qui 2/263:21 pm
ORD
- SXM
1 stop20h 54m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 2/171:38 pm
SXM
- MDW
1 stop10h 55m
Delta
sex 2/276:00 am
MDW
- SXM
1 stop6h 50m
Delta
Deal found 1/31![Delta logo]()
$546
This Orbitz deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 2/183:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
qui 2/265:15 am
ORD
- SXM
1 stop7h 00m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 2/183:20 pm
SXM
- ORD
2 stops21h 31m
Multiple Airlines
qui 2/268:16 pm
ORD
- SXM
1 stop15h 59m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 2/181:38 pm
SXM
- MDW
1 stop10h 53m
Delta
qui 2/266:00 am
MDW
- SXM
1 stop6h 50m
Delta
Deal found 1/31![Delta logo]()
$1,117
One-way flights from St. Maarten to ChicagoSearch for one-way flight options from St. Maarten to Chicago. Find affordable one-way fares based on user searches. Data last updated fevereiro 2, 2026.
Search for one-way flight options from St. Maarten to Chicago. Find affordable one-way fares based on user searches. Data last updated fevereiro 2, 2026.
This Orbitz deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 2/193:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$149
This Travelocity deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 2/183:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$152
This Expedia deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 2/283:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$160
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 2/283:20 pm
SXM
- ORD
1 stop9h 19m
Frontier
Deal found 2/2![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 2/253:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
qui 2/263:20 pm
SXM
- ORD
1 stop9h 45m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$179
This FlightHub deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 2/213:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
qua 3/43:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 2/273:20 pm
SXM
- ORD
2 stops18h 34m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$201
This Orbitz deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 2/213:20 pm
SXM
- ORD
1 stop9h 19m
Frontier
Deal found 1/31![Frontier logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 4/302:11 pm
SXM
- ORD
1 stop10h 30m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” 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.
qua 4/12:35 pm
SXM
- MDW
2 stops33h 38m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$330
Find flight deals from St. Maarten to Chicago
Keep the following information in mind while searching for St. Maarten to Chicago flight deals. Data was last updated fevereiro 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $251 (Orbitz) |
One-way from | $149 (Orbitz) |
Good one-way deal | $582 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from St. Maarten to Chicago 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 fevereiro 2, 2026.
Use the filters below to find and compare flights from St. Maarten to Chicago that are best for you.
Fly from
St. Maarten
Fly to
Chicago
Route
Depart
Return
Price
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
qua 2/18
3:20 pm-11:47 pm
1 stop10h 27m
Chicago O'Hare Intl
qui 2/26
5:15 am-2:15 pm
1 stop7h 00m
$251
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
sáb 2/14
3:20 pm-11:47 pm
1 stop10h 27m
Chicago O'Hare Intl
sáb 2/21
5:15 am-2:15 pm
1 stop7h 00m
$273
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
ter 2/17
3:20 pm-11:22 am
1 stop22h 02m
Chicago O'Hare Intl
sex 2/27
8:16 pm-2:15 pm
1 stop15h 59m
$282
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
ter 2/17
3:20 pm-4:52 pm
2 stops27h 32m
Chicago O'Hare Intl
sex 2/27
8:16 pm-2:15 pm
1 stop15h 59m
$292
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
ter 3/17
2:20 pm-11:17 pm
1 stop9h 57m
Chicago O'Hare Intl
ter 3/24
5:05 am-1:15 pm
1 stop7h 10m
$314
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
ter 2/17
3:20 pm-10:39 am
2 stops21h 19m
Chicago O'Hare Intl
qui 2/26
3:21 pm-2:15 pm
1 stop20h 54m
$345
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
qua 5/6
2:11 pm-11:41 pm
1 stop10h 30m
Chicago O'Hare Intl
dom 5/10
5:15 am-1:16 pm
1 stop7h 01m
$349
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
qui 5/7
2:11 pm-11:41 pm
1 stop10h 30m
Chicago O'Hare Intl
dom 5/10
5:15 am-1:16 pm
1 stop7h 01m
$350
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
qua 2/18
3:20 pm-10:51 am
2 stops21h 31m
Chicago O'Hare Intl
qui 2/26
8:16 pm-2:15 pm
1 stop15h 59m
$352
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
seg 2/16
3:20 pm-11:47 pm
1 stop10h 27m
Chicago O'Hare Intl
qui 2/26
5:15 am-2:15 pm
1 stop7h 00m
$429
Showing 1-10 of 35 results
Best time to book a flight from St. Maarten to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from St. Maarten with our price prediction graph.
SXM-ORD
SXM-MDW
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 St. Maarten to Chicago
SX0-CHI
SXM-ORD
SXM-MDW
What is the cheapest time of day to fly from SX to CHI?
Find hourly flight availability from St. Maarten to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated fevereiro 2, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from St. Maarten to Chicago as you normally would.
Related info for your journey
Find useful and relevant information for your journey from St. Maarten to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
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