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$170+ 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 2/13. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — ORD
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap 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 December 15, 2025.

This Delta deal was found by Cheapflights users on 12/14. 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.
Thu 12/184:15 pmSXM - ORD
1 stop17h 40mDelta
Wed 12/245:30 amORD - SXM
1 stop7h 20mDelta
Deal found 12/14$494
This Kissandfly.com deal was found by Cheapflights users on 12/13. 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 12/212:20 pmSXM - ORD
Nonstop6h 01mLufthansa
Sun 12/288:45 amORD - SXM
Nonstop5h 12mLufthansa
Deal found 12/13$584
This Gotogate deal was found by Cheapflights users on 12/14. 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 12/213:40 pmSXM - ORD
1 stop30h 30mAir Canada
Sun 12/288:30 pmORD - SXM
2 stops40h 10mAir Canada
Deal found 12/14$611
This United Airlines deal was found by Cheapflights users on 12/13. 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.
Sun 12/212:20 pmSXM - ORD
Nonstop6h 01mUnited Airlines
Sun 12/288:45 amORD - SXM
Nonstop5h 12mUnited Airlines
Deal found 12/13$628
This Trip.com deal was found by Cheapflights users on 12/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/183:40 pmSXM - ORD
2 stops19h 33mMultiple Airlines
Wed 12/245:00 amORD - SXM
1 stop7h 15mMultiple Airlines
Deal found 12/14$631
This Mytrip deal was found by Cheapflights users on 12/14. 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 12/211:45 pmSXM - ORD
2 stops12h 45mMultiple Airlines
Sun 12/2812:09 pmORD - SXM
3 stops24h 06mMultiple Airlines
Deal found 12/14$752
This JetBlue deal was found by Cheapflights users on 12/13. 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 12/211:59 pmSXM - ORD
1 stop30h 47mJetBlue
Sun 12/287:41 pmORD - SXM
1 stop15h 03mJetBlue
Deal found 12/13$768
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
Sun 12/214:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Sun 12/286:00 amMDW - SXM
2 stops30h 15mMultiple Airlines
Deal found 12/14$849
This Delta deal was found by Cheapflights users on 12/14. 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 12/211:45 pmSXM - MDW
1 stop10h 37mDelta
Sun 12/286:00 amMDW - SXM
1 stop6h 50mDelta
Deal found 12/14$1,274

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 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$351
(Priceline)

One-way from

$170
(Kiwi.com)

Good one-way deal

$294 or less
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.
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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 December 15, 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

Wed 1/28

9:35 am-4:37 pm

2 stops33h 02m

Chicago O'Hare Intl

Wed 2/4

5:32 pm-2:10 pm

1 stop18h 38m

$374

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 1/28

1:55 pm-10:22 pm

1 stop10h 27m

Chicago Midway

Wed 2/4

6:00 am-2:55 pm

1 stop6h 55m

$492

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 12/18

4:15 pm-7:55 am

1 stop17h 40m

Chicago O'Hare Intl

Wed 12/24

5:30 am-2:50 pm

1 stop7h 20m

$494

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

5:26 pm-12:38 pm

1 stop17h 12m

$521

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 1/22

3:40 pm-6:51 pm

1 stop29h 11m

Chicago O'Hare Intl

Sun 1/25

9:15 pm-2:40 pm

2 stops39h 25m

$526

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 1/28

1:05 pm-10:05 am

2 stops23h 00m

Chicago Midway

Wed 2/4

11:00 am-11:55 am

2 stops22h 55m

$993

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 1/22

4:20 pm-5:55 pm

2 stops27h 35m

Chicago Midway

Mon 1/26

9:33 am-3:21 pm

2 stops27h 48m

$3,176

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 2/13

3:15 pm-7:50 pm

1 stop30h 35m

$170

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 1/12

3:15 pm-11:22 am

1 stop22h 07m

$170

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 2/12

3:15 pm-11:24 pm

1 stop10h 09m

$170

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 26 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 December 15, 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?

    Delta and American Airlines can get you from St. Maarten to Illinois in just under 5h 47m. Your travel time can differ by up to 4h 40m. 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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