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$163+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — ORD
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
1 adult, Economy
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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 January 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$261
(Trip.com)

One-way from

$163
(Super.com)
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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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 January 6, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/6. 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.
Thu 1/153:15 pmSXM - ORD
1 stop10h 31mSpirit Airlines
Wed 2/185:15 amORD - SXM
1 stop7h 00mSpirit Airlines
Deal found 1/6$237
This Trip.com deal was found by Cheapflights users on 1/6. 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.
Fri 2/203:20 pmSXM - ORD
1 stop10h 27mSpirit Airlines
Fri 2/278:16 pmORD - SXM
1 stop15h 59mSpirit Airlines
Deal found 1/6$261
This Mytrip deal was found by Cheapflights users on 1/6. 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.
Thu 1/223:15 pmSXM - ORD
1 stop10h 31mSpirit Airlines
Wed 1/2812:42 pmORD - SXM
2 stops23h 28mSpirit Airlines
Deal found 1/6$264
This Mytrip deal was found by Cheapflights users on 1/6. 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 1/243:15 pmSXM - ORD
1 stop10h 31mSpirit Airlines
Sat 1/3110:07 amORD - SXM
2 stops26h 08mSpirit Airlines
Deal found 1/6$268
This Mytrip deal was found by Cheapflights users on 1/5. 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 1/243:15 pmSXM - ORD
1 stop10h 31mSpirit Airlines
Fri 1/305:53 pmORD - SXM
2 stops18h 17mSpirit Airlines
Deal found 1/5$277
This Kiwi.com deal was found by Cheapflights users on 1/5. 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.
Sat 1/313:15 pmSXM - ORD
1 stop8h 48mSpirit Airlines
Sat 2/75:32 pmORD - SXM
1 stop18h 43mSpirit Airlines
Deal found 1/5$281
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Sat 1/173:15 pmSXM - ORD
1 stop10h 31mMultiple Airlines
Sat 2/2112:06 pmORD - SXM
1 stop24h 09mMultiple Airlines
Deal found 1/6$283
This Mytrip deal was found by Cheapflights users on 1/6. 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
1 stop10h 31mSpirit Airlines
Sun 2/155:15 amORD - SXM
1 stop7h 00mSpirit Airlines
Deal found 1/6$294
This Cheapflightsfares deal was found by Cheapflights users on 1/6. 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.
Fri 1/163:15 pmSXM - ORD
1 stop10h 31mSpirit Airlines
Wed 2/185:15 amORD - SXM
1 stop7h 00mSpirit Airlines
Deal found 1/6$306
This Frontier deal was found by Cheapflights users on 1/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/243:10 pmSXM - MDW
1 stop22h 35mFrontier
Fri 1/306:20 amMDW - SXM
1 stop29h 39mFrontier
Deal found 1/5$320
This Delta deal was found by Cheapflights users on 1/6. 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 1/221:55 pmSXM - MDW
1 stop10h 27mDelta
Wed 1/286:00 amMDW - SXM
1 stop6h 55mDelta
Deal found 1/6$500
This Delta deal was found by Cheapflights users on 1/6. 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 1/245:28 pmSXM - MDW
1 stop18h 25mDelta
Sat 1/315:00 pmMDW - SXM
2 stops17h 30mDelta
Deal found 1/6$559

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 6, 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

Fri 2/20

3:20 pm-11:47 pm

1 stop10h 27m

Chicago O'Hare Intl

Fri 2/27

8:16 pm-2:15 pm

1 stop15h 59m

$261

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 1/22

3:15 pm-11:46 pm

1 stop10h 31m

Chicago O'Hare Intl

Wed 1/28

12:42 pm-2:10 pm

2 stops23h 28m

$264

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/24

3:15 pm-11:46 pm

1 stop10h 31m

Chicago O'Hare Intl

Sat 1/31

10:07 am-2:15 pm

2 stops26h 08m

$268

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/31

3:15 pm-10:03 pm

1 stop8h 48m

Chicago O'Hare Intl

Sat 2/7

5:32 pm-2:15 pm

1 stop18h 43m

$277

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 1/24

3:10 pm-11:45 am

1 stop22h 35m

Chicago Midway

Fri 1/30

6:20 am-1:59 pm

1 stop29h 39m

$320

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

$324

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/17

3:15 pm-3:51 pm

2 stops26h 36m

Chicago O'Hare Intl

Sat 2/21

4:43 pm-2:15 pm

1 stop19h 32m

$328

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 1/16

5:00 pm-6:55 pm

2 stops27h 55m

Chicago O'Hare Intl

Wed 2/18

5:15 am-2:15 pm

1 stop7h 00m

$333

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 1/22

1:55 pm-10:22 pm

1 stop10h 27m

Chicago Midway

Wed 1/28

6:00 am-2:55 pm

1 stop6h 55m

$500

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 1/24

5:28 pm-9:53 am

1 stop18h 25m

Chicago Midway

Sat 1/31

5:00 pm-12:30 pm

2 stops17h 30m

$559

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 36 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 January 6, 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.

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?

    Spirit Airlines, Frontier, and Delta can get you from St. Maarten to Illinois in just under 10h 27m. Your travel time can differ by up to 12h 08m. 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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