$150+ Cheap flights from St. Maarten to Illinois
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 — ORD
Jan 21 — Jan 281
1 adult, Economy
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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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Best flights from St. Maarten to IllinoisDiscover carefully curated flight deals from St. Maarten to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 22, 2025.
Discover carefully curated flight deals from St. Maarten to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 22, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 12/20. Clicking the “Pick Dates” 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 2/143:20 pmSXM - ORD
1 stop10h 27mSpirit Airlines
Sat 2/215:15 amORD - SXM
1 stop7h 00mSpirit Airlines
Deal found 12/20![Spirit Airlines logo]()
$268
This Flysmarter deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/175:00 pmSXM - ORD
2 stops20h 06mAir Canada
Sat 1/246:28 pmORD - SXM
2 stops18h 12mAir Canada
Deal found 12/21![Air Canada logo]()
$421
This Priceline deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” 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.
Wed 2/43:43 pmSXM - ORD
1 stop29h 48mMultiple Airlines
Wed 2/1112:50 pmORD - SXM
1 stop23h 50mMultiple Airlines
Deal found 12/21![Multiple Airlines logo]()
$497
This American Airlines deal was found by Cheapflights users on 12/20. Clicking the “Pick Dates” 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.
Sat 2/143:00 pmSXM - ORD
Nonstop5h 47mAmerican Airlines
Sat 2/216:48 pmORD - SXM
1 stop17h 17mAmerican Airlines
Deal found 12/20![American Airlines logo]()
$521
This Delta deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” 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.
Sat 1/171:55 pmSXM - MDW
1 stop10h 12mDelta
Sat 1/246:25 amMDW - SXM
1 stop7h 38mDelta
Deal found 12/21![Delta logo]()
$713
This Mytrip deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” 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.
Sat 1/173:15 pmSXM - ORD
2 stops19h 57mSpirit Airlines
Sat 1/2412:44 pmORD - SXM
3 stops23h 26mSpirit Airlines
Deal found 12/21![Spirit Airlines logo]()
$359
This Mytrip deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” 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.
Wed 2/45:00 pmSXM - ORD
2 stops27h 55mAir Canada
Wed 2/111:55 pmORD - SXM
2 stops22h 45mAir Canada
Deal found 12/21![Air Canada logo]()
$510
This Mytrip deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” 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.
Wed 2/41:05 pmSXM - MDW
2 stops23h 00mMultiple Airlines
Wed 2/1111:00 amMDW - SXM
3 stops25h 40mMultiple Airlines
Deal found 12/21![Multiple Airlines logo]()
$682
This Delta deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/41:55 pmSXM - MDW
1 stop10h 27mDelta
Wed 2/116:00 amMDW - SXM
1 stop6h 55mDelta
Deal found 12/21![Delta logo]()
$748
This WestJet deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” 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.
Wed 2/44:20 pmSXM - MDW
2 stops27h 35mWestJet
Wed 2/111:26 pmMDW - SXM
2 stops23h 51mWestJet
Deal found 12/21![WestJet logo]()
$3,563
Find flight deals from St. Maarten to Illinois
Keep the following information in mind while searching for St. Maarten to Illinois flight deals. Data was last updated December 22, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $258 (Kiwi.com) |
One-way from | $150 (Super.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from St. Maarten to Illinois 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 December 22, 2025.
Use the filters below to find and compare flights from St. Maarten to Illinois that are best for you.
Fly from
St. Maarten
Fly to
Illinois
Route
Depart
Return
Price
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Sat 2/14
3:20 pm-11:47 pm
1 stop10h 27m
Chicago O'Hare Intl
Sat 2/21
5:15 am-2:15 pm
1 stop7h 00m
$268
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Sat 1/17
3:15 pm-9:12 am
2 stops19h 57m
Chicago O'Hare Intl
Sat 1/24
12:44 pm-2:10 pm
3 stops23h 26m
$359
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Sat 1/17
5:00 pm-11:06 am
2 stops20h 06m
Chicago O'Hare Intl
Sat 1/24
6:28 pm-2:40 pm
2 stops18h 12m
$421
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Wed 2/4
3:43 pm-7:31 pm
1 stop29h 48m
Chicago O'Hare Intl
Wed 2/11
12:50 pm-2:40 pm
1 stop23h 50m
$497
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Wed 2/4
5:00 pm-6:55 pm
2 stops27h 55m
Chicago O'Hare Intl
Wed 2/11
1:55 pm-2:40 pm
2 stops22h 45m
$510
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Sat 2/14
3:00 pm-6:47 pm
Nonstop5h 47m
Chicago O'Hare Intl
Sat 2/21
6:48 pm-2:05 pm
1 stop17h 17m
$521
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Wed 2/4
1:05 pm-10:05 am
2 stops23h 00m
Chicago Midway
Wed 2/11
11:00 am-2:40 pm
3 stops25h 40m
$682
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Sat 1/17
1:55 pm-10:07 pm
1 stop10h 12m
Chicago Midway
Sat 1/24
6:25 am-4:03 pm
1 stop7h 38m
$713
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Wed 2/4
1:55 pm-10:22 pm
1 stop10h 27m
Chicago Midway
Wed 2/11
6:00 am-2:55 pm
1 stop6h 55m
$748
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Wed 2/4
4:20 pm-5:55 pm
2 stops27h 35m
Chicago Midway
Wed 2/11
1:26 pm-3:17 pm
2 stops23h 51m
$3,563
Showing 1-10 of 24 results
Best time to book a flight from St. Maarten to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from St. Maarten with our price prediction graph.
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 Illinois
What is the cheapest time of day to fly from SX to IL?
Find hourly flight availability from St. Maarten to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 22, 2025.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from St. Maarten to Illinois as you normally would.