$171+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — ORD
Feb 20 — Feb 271
1 adult, Economy
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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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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 Illinois
Cheapest flights from St. Maarten to IllinoisExplore the most affordable flight options available from St. Maarten to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.
Explore the most affordable flight options available from St. Maarten to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.
This Vliegwinkel deal was found by Cheapflights users on 1/20. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/143:20 pm
SXM
- ORD
1 stop10h 27m
Multiple Airlines
Sat 2/2112:50 pm
ORD
- SXM
1 stop23h 50m
Multiple Airlines
Deal found 1/20![Multiple Airlines logo]()
$289
This Mytrip deal was found by Cheapflights users on 1/21. 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 2/143:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
Sat 2/218:59 am
ORD
- SXM
2 stops27h 16m
Spirit Airlines
Deal found 1/21![Spirit Airlines logo]()
$292
This Vliegwinkel deal was found by Cheapflights users on 1/21. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/65:00 pm
SXM
- ORD
1 stop18h 13m
Multiple Airlines
Sun 2/88:43 pm
ORD
- SXM
1 stop15h 32m
Multiple Airlines
Deal found 1/21![Multiple Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 1/21. 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.
Fri 2/61:55 pm
SXM
- MDW
1 stop10h 27m
Delta
Sun 2/86:00 am
MDW
- SXM
1 stop6h 55m
Delta
Deal found 1/21![Delta logo]()
$520
This Delta deal was found by Cheapflights users on 1/21. 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 2/141:38 pm
SXM
- MDW
1 stop10h 53m
Delta
Sat 2/216:00 am
MDW
- SXM
1 stop6h 50m
Delta
Deal found 1/21![Delta logo]()
$580
This Mytrip deal was found by Cheapflights users on 1/21. 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 2/141:05 pm
SXM
- MDW
2 stops28h 15m
Multiple Airlines
Sat 2/2112:50 pm
MDW
- SXM
2 stops23h 50m
Multiple Airlines
Deal found 1/21![Multiple Airlines logo]()
$1,150
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 January 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $289 (Vliegwinkel) |
One-way from | $171 (FlightHub) |
Good one-way deal | $582 or less |
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 January 21, 2026.
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
12:50 pm-2:40 pm
1 stop23h 50m
$289
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
8:59 am-2:15 pm
2 stops27h 16m
$292
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Fri 2/6
5:00 pm-9:13 am
1 stop18h 13m
Chicago O'Hare Intl
Sun 2/8
8:43 pm-2:15 pm
1 stop15h 32m
$320
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Sat 3/7
3:20 pm-11:47 pm
1 stop10h 27m
Chicago O'Hare Intl
Sat 3/14
8:41 pm-1:08 pm
1 stop15h 27m
$340
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Fri 2/6
1:55 pm-10:22 pm
1 stop10h 27m
Chicago Midway
Sun 2/8
6:00 am-2:55 pm
1 stop6h 55m
$520
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Sat 2/14
1:38 pm-10:31 pm
1 stop10h 53m
Chicago Midway
Sat 2/21
6:00 am-2:50 pm
1 stop6h 50m
$580
Simpson BayChicago
SXM - MDW
SXMMDW
Simpson Bay Princess Juliana
Sat 2/14
1:05 pm-3:20 pm
2 stops28h 15m
Chicago Midway
Sat 2/21
12:50 pm-2:40 pm
2 stops23h 50m
$1,150
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Sat 2/21
3:20 pm-10:39 pm
1 stop9h 19m
$171
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Tue 2/17
3:20 pm-11:22 am
1 stop22h 02m
$178
Simpson BayChicago
SXM - ORD
SXMORD
Simpson Bay Princess Juliana
Tue 3/17
2:14 pm-11:17 pm
1 stop10h 03m
$178
Showing 1-10 of 25 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 January 21, 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 Illinois as you normally would.