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St. Maarten

$74+ Cheap flights from Illinois to St. Maarten

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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Feb 24 — Mar 31
Tue 2/24
Tue 3/3
1 adult, Economy
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Cheap flight deals from Illinois to St. Maarten

Cheapest flights from Illinois to St. Maarten
Explore the most affordable flight options available from Illinois to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 25, 2026.

This Super.com deal was found by Cheapflights users on 1/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/88:43 pm
ORD
-
SXM
1 stop15h 32m
Spirit Airlines
Sat 2/143:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/23$230
This Super.com deal was found by Cheapflights users on 1/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/88:43 pm
ORD
-
SXM
1 stop15h 32m
Spirit Airlines
Fri 2/203:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/25$237
This CheapOair deal was found by Cheapflights users on 1/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/185:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Wed 2/253:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/23$238
This Travelocity deal was found by Cheapflights users on 1/23. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/75:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Sat 2/143:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/23$240
This Expedia deal was found by Cheapflights users on 1/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/85:15 am
ORD
-
SXM
1 stop7h 00m
Multiple Airlines
Sat 2/213:20 pm
SXM
-
ORD
1 stop9h 19m
Multiple Airlines
Deal found 1/23$241
This Cheapflightsfares deal was found by Cheapflights users on 1/23. 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.
Mon 2/95:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Wed 2/183:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Deal found 1/23$249
This Expedia deal was found by Cheapflights users on 1/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/88:43 pm
ORD
-
SXM
1 stop15h 32m
Multiple Airlines
Sat 2/143:20 pm
SXM
-
ORD
1 stop9h 19m
Multiple Airlines
Deal found 1/23$258
This Air Canada deal was found by Cheapflights users on 1/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/34:05 pm
STL
-
SXM
1 stop21h 55m
Air Canada
Fri 3/134:00 pm
SXM
-
STL
1 stop24h 29m
Air Canada
Deal found 1/25$365
This Air Canada deal was found by Cheapflights users on 1/24. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/34:05 pm
STL
-
SXM
1 stop21h 55m
Air Canada
Mon 3/94:00 pm
SXM
-
STL
1 stop24h 29m
Air Canada
Deal found 1/24$375
This Air Canada deal was found by Cheapflights users on 1/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/34:05 pm
STL
-
SXM
1 stop21h 55m
Air Canada
Tue 3/104:00 pm
SXM
-
STL
1 stop24h 29m
Air Canada
Deal found 1/22$377
This Air Canada deal was found by Cheapflights users on 1/23. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/244:05 pm
STL
-
SXM
2 stops20h 35m
Air Canada
Sat 1/315:00 pm
SXM
-
STL
1 stop24h 29m
Air Canada
Deal found 1/23$420
This Air Canada deal was found by Cheapflights users on 1/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/84:05 pm
STL
-
SXM
1 stop21h 55m
Air Canada
Fri 3/134:00 pm
SXM
-
STL
1 stop24h 29m
Air Canada
Deal found 1/22$427

Find flight deals from Illinois to St. Maarten

Keep the following information in mind while searching for Illinois to St. Maarten flight deals. Data was last updated January 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$230
(Super.com)

One-way from

$74
(Super.com)

Popular in

December

Cheapest in

January

Average price

$586

Good round-trip deal

$596 or less
Provider with most accurate pricing for Chicago (CHI)-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Simpson Bay Princess Juliana flights.
Search Deals
From Illinois to St. Maarten
Search Deals
One-way flight from Illinois to St. Maarten
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Illinois to St. Maarten.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to St. Maarten 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 25, 2026.
Use the filters below to find and compare flights from Illinois to St. Maarten that are best for you.

Fly from

Illinois

Fly to

St. Maarten

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/7

5:32 pm-2:15 pm

1 stop18h 43m

Simpson Bay Princess Juliana

Thu 2/12

3:20 pm-11:24 pm

1 stop10h 04m

$273

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/4

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Mon 3/9

2:20 pm-11:47 pm

1 stop10h 27m

$289

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/7

5:53 pm-2:15 pm

2 stops18h 22m

Simpson Bay Princess Juliana

Sat 2/14

3:20 pm-11:47 pm

1 stop10h 27m

$307

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/7

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sun 2/15

3:20 pm-11:47 pm

1 stop10h 27m

$320

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 2/5

8:43 pm-2:15 pm

1 stop15h 32m

Simpson Bay Princess Juliana

Tue 2/17

3:20 pm-11:22 am

1 stop22h 02m

$326

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 5/2

5:15 am-1:16 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Sat 5/9

2:11 pm-11:41 pm

1 stop10h 30m

$329

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/8

9:23 am-2:15 pm

3 stops26h 52m

Simpson Bay Princess Juliana

Fri 2/20

3:20 pm-11:47 pm

1 stop10h 27m

$330

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 2/4

5:32 pm-2:15 pm

1 stop18h 43m

Simpson Bay Princess Juliana

Mon 2/9

3:20 pm-11:47 am

2 stops22h 27m

$334

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/8

8:43 pm-2:15 pm

1 stop15h 32m

Simpson Bay Princess Juliana

Sun 2/15

3:20 pm-11:24 pm

1 stop10h 04m

$345

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/18

5:15 am-1:16 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Sat 4/25

2:11 pm-11:41 pm

1 stop10h 30m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

Showing 1-10 of 46 results
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Best time to book a flight from Illinois to St. Maarten

Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Illinois 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 Illinois to St. Maarten

What is the cheapest month to book a flight from Illinois to St. Maarten?

Currently, February is the cheapest month in which you can book a flight from Illinois to St. Maarten (average of $241). Flying from Illinois to St. Maarten in June is currently the most expensive (average of $595). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IL to SX?

Find hourly flight availability from Illinois to St. Maarten. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 25, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to St. Maarten as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Illinois to St. Maarten. 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 Illinois to St. Maarten?

    Departing from Illinois to St. Maarten will take you 15h 59m. 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 Illinois to St. Maarten that include hotel bookings?

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

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

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

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

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

  • What is the cheapest month to book a flight from Illinois to St. Maarten?

    Currently, February is the cheapest month in which you can book a flight from Illinois to St. Maarten (average of $241). Flying from Illinois to St. Maarten in June is currently the most expensive (average of $595). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to St. Maarten

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Illinois to St. Maarten

Discover the top 5 airlines that operate flights from Illinois to St. Maarten. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$280Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$290Average$612FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$410Average$763FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$501Average$691FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$535Average$731FlexibilityNo cancel feeOn-time62%

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