St. Maarten

$156+ 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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Jul 7 — Jul 141
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Cheap 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 July 2, 2025.

Round-trip from

$357
(Cheapflightsfares)

One-way from

$156
(Booking.com)

Popular in

March

Cheapest in

September

Average price

$695

Good round-trip deal

$707 or less
From Illinois to St. Maarten
One-way flight from Illinois to St. Maarten
Highest demand for flights based on searches. 5% potential increase in price ($42 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Illinois to St. Maarten.

Find 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 July 2, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/1. 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.
Wed 8/135:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Wed 8/203:05 pmSXM - ORD
1 stop9h 54mSpirit Airlines
Deal found 7/1$357
This Priceline deal was found by Cheapflights users on 6/29. 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.
Sat 10/185:05 amORD - SXM
1 stop8h 19mMultiple Airlines
Sat 11/11:58 pmSXM - ORD
1 stop24h 59mMultiple Airlines
Deal found 6/29$358
This Trip.com deal was found by Cheapflights users on 7/1. 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 8/75:26 pmSTL - SXM
1 stop19h 34mSpirit Airlines
Mon 8/113:05 pmSXM - STL
1 stop26h 26mSpirit Airlines
Deal found 7/1$440
This Expedia deal was found by Cheapflights users on 6/29. 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.
Thu 7/39:12 pmMDW - SXM
2 stops19h 04mFrontier
Sat 7/56:26 pmSXM - MDW
2 stops45h 40mFrontier
Deal found 6/29$498
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Thu 7/319:12 pmMDW - SXM
2 stops15h 48mMultiple Airlines
Thu 8/72:10 pmSXM - MDW
1 stop19h 35mMultiple Airlines
Deal found 7/2$549
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Fri 10/172:12 pmSTL - SXM
2 stops23h 12mMultiple Airlines
Wed 10/223:27 pmSXM - STL
1 stop28h 05mMultiple Airlines
Deal found 7/2$565
This Delta deal was found by Cheapflights users on 7/1. 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.
Mon 8/186:04 amMDW - SXM
1 stop6h 52mDelta
Wed 8/273:10 pmSXM - MDW
2 stops22h 18mDelta
Deal found 7/1$580
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Tue 12/25:27 amSTL - SXM
1 stop6h 48mAmerican Airlines
Tue 12/93:15 pmSXM - STL
1 stop9h 50mAmerican Airlines
Deal found 7/2$583
This Travelocity deal was found by Cheapflights users on 7/1. 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.
Thu 8/78:44 pmSTL - SXM
2 stops37h 44mFrontier
Mon 8/116:26 pmSXM - STL
2 stops30h 21mFrontier
Deal found 7/1$585
This Delta deal was found by Cheapflights users on 7/1. 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 10/116:00 amSTL - SXM
1 stop6h 47mDelta
Sat 10/183:15 pmSXM - STL
1 stop7h 44mDelta
Deal found 7/1$633
This Cheapflightsfares deal was found by Cheapflights users on 7/1. 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 12/152:00 pmMDW - SXM
2 stops23h 17mWestJet
Mon 12/224:10 pmSXM - MDW
2 stops21h 08mWestJet
Deal found 7/1$3,323

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 July 2, 2025.
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

Wed 8/13

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Wed 8/20

3:05 pm-11:59 pm

1 stop9h 54m

$357

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 7/11

4:26 pm-11:28 am

1 stop18h 02m

Simpson Bay Princess Juliana

Wed 7/23

3:05 pm-11:13 pm

1 stop9h 08m

$370

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Thu 8/7

5:26 pm-2:00 pm

1 stop19h 34m

Simpson Bay Princess Juliana

Mon 8/11

3:05 pm-4:31 pm

1 stop26h 26m

$440

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 7/31

9:12 pm-2:00 pm

2 stops15h 48m

Simpson Bay Princess Juliana

Thu 8/7

2:10 pm-8:45 am

1 stop19h 35m

$549

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Fri 10/17

2:12 pm-2:24 pm

2 stops23h 12m

Simpson Bay Princess Juliana

Wed 10/22

3:27 pm-6:32 pm

1 stop28h 05m

$565

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 8/18

6:04 am-1:56 pm

1 stop6h 52m

Simpson Bay Princess Juliana

Wed 8/27

3:10 pm-12:28 pm

2 stops22h 18m

$580

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Tue 12/2

5:27 am-2:15 pm

1 stop6h 48m

Simpson Bay Princess Juliana

Tue 12/9

3:15 pm-11:05 pm

1 stop9h 50m

$583

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Thu 8/7

8:44 pm-11:28 am

2 stops37h 44m

Simpson Bay Princess Juliana

Mon 8/11

6:26 pm-11:47 pm

2 stops30h 21m

$585

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sat 10/11

6:00 am-1:47 pm

1 stop6h 47m

Simpson Bay Princess Juliana

Sat 10/18

3:15 pm-9:59 pm

1 stop7h 44m

$633

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 7/16

9:24 am-1:15 pm

2 stops26h 51m

Simpson Bay Princess Juliana

Sun 7/20

2:10 pm-5:39 pm

2 stops28h 29m

$3,560

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 20 results
1
2

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, September is the cheapest month in which you can book a flight from Illinois to St. Maarten (average of $459). Flying from Illinois to St. Maarten in March is currently the most expensive (average of $656). 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 July 2, 2025.

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.

Reviews of airlines servicing St. Maarten

Get insights into the airlines that provide service to St. Maarten. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to St. Maarten. Reviews last updated July 2, 2025.
Read through reviews of airlines operating flights from Illinois to St. Maarten, such as Delta, Copa Airlines, and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good
8.0
Very good

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
8.0
Very good

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $156. Users have also found prices from $253 and $293 on Frontier and Delta, respectively.

  • 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, September is the cheapest month in which you can book a flight from Illinois to St. Maarten (average of $459). Flying from Illinois to St. Maarten in March is currently the most expensive (average of $656). 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

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Alternative routes for Illinois to St. Maarten

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

Top 4 airlines flying from Illinois to St. Maarten

Discover the top 4 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 July 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$330Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$425Average$683FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$579Average$740FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$654Average$895FlexibilityNo cancel feeOn-time69%

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