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$135+ 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 12/20. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — ORD
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
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 20, 2025.

This Mytrip deal was found by Cheapflights users on 11/19. 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 12/63:20 pmSXM - ORD
2 stops23h 27mSpirit Airlines
Sat 12/135:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Deal found 11/19$353
This Delta deal was found by Cheapflights users on 11/19. 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 12/63:25 pmSXM - MDW
1 stop10h 22mDelta
Sat 12/136:00 amMDW - SXM
1 stop6h 50mDelta
Deal found 11/19$368
This Delta deal was found by Cheapflights users on 11/19. 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 12/63:25 pmSXM - ORD
1 stop9h 18mDelta
Sat 12/135:30 amORD - SXM
1 stop7h 20mDelta
Deal found 11/19$368
This Delta deal was found by Cheapflights users on 11/18. 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 12/123:53 pmSXM - MDW
1 stop9h 54mDelta
Sun 12/146:00 amMDW - SXM
1 stop6h 28mDelta
Deal found 11/18$377
This Delta deal was found by Cheapflights users on 11/19. 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 12/123:53 pmSXM - ORD
1 stop10h 08mDelta
Sun 12/145:30 amORD - SXM
1 stop6h 58mDelta
Deal found 11/19$377
This Mytrip deal was found by Cheapflights users on 11/19. 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.
Mon 12/293:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Tue 12/309:09 pmORD - SXM
2 stops15h 06mSpirit Airlines
Deal found 11/19$400
This Kissandfly.com deal was found by Cheapflights users on 11/19. 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.
Sat 12/62:40 pmSXM - ORD
Nonstop6h 00mLufthansa
Sat 12/138:45 amORD - SXM
Nonstop5h 12mLufthansa
Deal found 11/19$412
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Fri 12/123:20 pmSXM - ORD
2 stops23h 48mAmerican Airlines
Sun 12/148:55 pmORD - SXM
2 stops17h 30mAmerican Airlines
Deal found 11/19$437
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/64:00 pmSXM - ORD
Nonstop5h 54mAmerican Airlines
Sat 12/138:05 amORD - SXM
Nonstop5h 03mAmerican Airlines
Deal found 11/19$443
This Mytrip deal was found by Cheapflights users on 11/19. 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 12/65:00 pmSXM - MDW
2 stops22h 10mMultiple Airlines
Sat 12/131:50 pmMDW - SXM
2 stops23h 31mMultiple Airlines
Deal found 11/19$1,570

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 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$353
(Mytrip)

One-way from

$135
(Frontier)

Good one-way deal

$389 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 November 20, 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 - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 12/6

3:25 pm-11:47 pm

1 stop10h 22m

Chicago Midway

Sat 12/13

6:00 am-2:50 pm

1 stop6h 50m

$368

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/6

3:25 pm-10:43 pm

1 stop9h 18m

Chicago O'Hare Intl

Sat 12/13

5:30 am-2:50 pm

1 stop7h 20m

$368

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 3/6

4:55 pm-7:29 am

1 stop16h 34m

Chicago O'Hare Intl

Tue 3/10

6:00 am-2:51 pm

1 stop7h 51m

$377

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 12/12

3:53 pm-11:47 pm

1 stop9h 54m

Chicago Midway

Sun 12/14

6:00 am-2:28 pm

1 stop6h 28m

$377

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 12/12

3:53 pm-12:01 am

1 stop10h 08m

Chicago O'Hare Intl

Sun 12/14

5:30 am-2:28 pm

1 stop6h 58m

$377

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 2/14

3:11 pm-12:18 am

1 stop11h 07m

Chicago O'Hare Intl

Sat 2/21

5:15 am-2:16 pm

1 stop7h 01m

$385

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/6

3:20 pm-2:21 pm

3 stops25h 01m

Chicago O'Hare Intl

Sat 12/13

5:00 am-2:15 pm

1 stop7h 15m

$392

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 12/29

3:20 pm-12:30 am

1 stop11h 10m

Chicago O'Hare Intl

Tue 12/30

9:09 pm-2:15 pm

2 stops15h 06m

$400

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/6

2:40 pm-6:40 pm

Nonstop6h 00m

Chicago O'Hare Intl

Sat 12/13

6:25 pm-1:18 pm

1 stop16h 53m

$417

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

5:31 pm-1:10 pm

2 stops18h 39m

$437

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 29 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 20, 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, United Airlines, and Spirit Airlines can get you from St. Maarten to Illinois in just under 10h 22m. Your travel time can differ by up to 6h 12m. Airlines will cover a distance of 2189 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from St. Maarten to Illinois one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $135. However, be on the lookout for offers from Spirit Airlines and Delta, as they are both options that can get you from St. Maarten to Illinois for a low price.

  • 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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