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$148+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — ORD
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Find flight deals from St. Maarten to Illinois

Cheapest flights from St. Maarten to Illinois
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 November 13, 2025.

This Mytrip deal was found by Cheapflights users on 11/11. 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.
Fri 11/213:20 pmSXM - ORD
2 stops23h 36mSpirit Airlines
Fri 11/285:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Deal found 11/11$418
This Priceline deal was found by Cheapflights users on 11/11. 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 11/215:00 pmSXM - ORD
1 stop24h 10mMultiple Airlines
Fri 11/285:00 amORD - SXM
1 stop7h 15mMultiple Airlines
Deal found 11/11$421
This Gotogate deal was found by Cheapflights users on 11/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/283:40 pmSXM - ORD
2 stops29h 48mAir Canada
Sun 1/48:15 pmORD - SXM
2 stops40h 25mAir Canada
Deal found 11/11$513
This Mytrip deal was found by Cheapflights users on 11/11. 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.
Sun 12/2811:30 amSXM - ORD
3 stops25h 44mMultiple Airlines
Sun 1/412:09 pmORD - SXM
3 stops24h 06mMultiple Airlines
Deal found 11/11$604
This Kissandfly.com deal was found by Cheapflights users on 11/11. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/282:20 pmSXM - ORD
Nonstop6h 01mLufthansa
Sun 1/48:45 amORD - SXM
Nonstop5h 12mLufthansa
Deal found 11/11$623
This Delta deal was found by Cheapflights users on 11/11. 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 11/214:20 pmSXM - MDW
1 stop9h 20mDelta
Fri 11/286:00 amMDW - SXM
1 stop6h 55mDelta
Deal found 11/11$718
This Vliegwinkel deal was found by Cheapflights users on 11/11. 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 11/153:20 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Sat 11/225:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Deal found 11/11$729
This Delta deal was found by Cheapflights users on 11/11. 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.
Sun 12/281:45 pmSXM - MDW
1 stop10h 37mDelta
Sun 1/46:00 amMDW - SXM
1 stop6h 50mDelta
Deal found 11/11$828
This Mytrip deal was found by Cheapflights users on 11/11. 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.
Sun 12/283:40 pmSXM - MDW
3 stops21h 26mMultiple Airlines
Sun 1/411:48 amMDW - SXM
2 stops25h 33mMultiple Airlines
Deal found 11/11$939
This Mytrip deal was found by Cheapflights users on 11/11. 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.
Sun 12/284:20 pmSXM - MDW
2 stops20h 46mWestJet
Sun 1/411:48 amMDW - SXM
2 stops25h 33mWestJet
Deal found 11/11$966
This Delta deal was found by Cheapflights users on 11/11. 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 11/153:30 pmSXM - MDW
1 stop10h 10mDelta
Sat 11/224:28 pmMDW - SXM
1 stop20h 27mDelta
Deal found 11/11$1,157
This WestJet deal was found by Cheapflights users on 11/11. 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.
Fri 11/214:20 pmSXM - MDW
2 stops43h 32mWestJet
Fri 11/287:02 pmMDW - SXM
2 stops42h 19mWestJet
Deal found 11/11$3,440

Cheap 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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$377
(United Airlines)

One-way from

$148
(Super.com)

Good one-way deal

$389 or less
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago (CHI) flights.
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From St. Maarten to Illinois
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One-way flight from St. Maarten to Illinois
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Price to beat on a one-way flight from St. Maarten to Illinois.
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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 November 13, 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

Fri 3/6

4:55 pm-11:43 pm

1 stop8h 48m

Chicago O'Hare Intl

Tue 3/10

6:05 am-2:51 pm

1 stop7h 46m

$377

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/6

4:26 pm-3:23 pm

2 stops24h 57m

Chicago Midway

Tue 3/10

1:00 pm-11:15 am

2 stops21h 15m

$382

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 2/14

3:00 pm-6:54 pm

Nonstop5h 54m

Chicago O'Hare Intl

Sat 2/21

6:48 pm-2:19 pm

1 stop17h 31m

$397

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 3/6

5:33 pm-11:00 am

2 stops19h 27m

Chicago O'Hare Intl

Tue 3/10

7:00 pm-3:10 pm

2 stops19h 10m

$437

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 12/28

3:40 pm-7:28 pm

2 stops29h 48m

Chicago O'Hare Intl

Sun 1/4

8:15 pm-2:40 pm

2 stops40h 25m

$513

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 12/28

1:45 pm-10:22 pm

1 stop10h 37m

Chicago Midway

Sun 1/4

6:00 am-2:50 pm

1 stop6h 50m

$828

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 12/28

3:40 pm-11:06 am

3 stops21h 26m

Chicago Midway

Sun 1/4

11:48 am-3:21 pm

2 stops25h 33m

$939

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 12/28

4:20 pm-11:06 am

2 stops20h 46m

Chicago Midway

Sun 1/4

11:48 am-3:21 pm

2 stops25h 33m

$966

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/13

3:20 pm-12:09 am

1 stop10h 49m

$187

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 2/9

3:09 pm-8:54 pm

1 stop31h 45m

$191

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 25 results
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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 November 13, 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.

Related info for your journey

Find useful and relevant information for your journey from St. Maarten to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from St. Maarten to Illinois?

    United Airlines, Delta, and American Airlines can get you from St. Maarten to Illinois in just under 5h 54m. Your travel time can differ by up to 19h 03m. Airlines will cover a distance of 2204 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from St. Maarten to Illinois that include hotel bookings?

    Yes. In addition to deals on St. Maarten to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from St. Maarten to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from St. Maarten to Illinois.

  • Can I find deals for business class flights from St. Maarten to Illinois?

    Yes. Cheapflights offers flight deals from St. Maarten to Illinois by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for St. Maarten to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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