HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
St. Maarten

$128+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SXM
Nov 12 — Nov 191
Wed 11/12
Wed 11/19
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Illinois to St. Maarten with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 13, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$317
(Cheapflightsfares)

One-way from

$128
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$762

Good round-trip deal

$584 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
Highest demand for flights based on searches. 7% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Illinois to St. Maarten.
Search Deals

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 October 13, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/11. 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 11/35:10 amORD - SXM
1 stop7h 05mSpirit Airlines
Sat 11/83:20 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Deal found 10/11$317
This Cheapflightsfares deal was found by Cheapflights users on 10/11. 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.
Sat 11/85:10 amORD - SXM
1 stop7h 05mSpirit Airlines
Sat 11/153:20 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Deal found 10/11$354
This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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.
Sat 11/85:10 amORD - SXM
1 stop7h 05mSpirit Airlines
Fri 11/143:20 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Deal found 10/12$370
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Tue 12/93:21 pmORD - SXM
1 stop20h 49mSpirit Airlines
Wed 12/173:15 pmSXM - ORD
1 stop10h 19mSpirit Airlines
Deal found 10/12$374
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:00 amMDW - SXM
1 stop6h 55mDelta
Tue 11/254:20 pmSXM - MDW
1 stop9h 20mDelta
Deal found 10/13$375
This Delta deal was found by Cheapflights users on 10/11. 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 11/245:23 amORD - SXM
1 stop7h 32mDelta
Thu 11/274:20 pmSXM - ORD
1 stop8h 10mDelta
Deal found 10/11$375
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:48 pmMDW - SXM
2 stops18h 07mDelta
Wed 11/264:20 pmSXM - MDW
2 stops18h 34mDelta
Deal found 10/13$380
This Delta deal was found by Cheapflights users on 10/12. 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.
Tue 12/95:30 amORD - SXM
1 stop6h 58mDelta
Thu 12/184:15 pmSXM - ORD
2 stops19h 45mDelta
Deal found 10/12$380
This Gotogate deal was found by Cheapflights users on 10/11. 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 10/267:43 pmORD - SXM
1 stop17h 17mSpirit Airlines
Sat 11/83:20 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Deal found 10/11$384
This American Airlines deal was found by Cheapflights users on 10/12. 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 12/137:07 pmORD - SXM
1 stop19h 18mAmerican Airlines
Thu 12/185:33 pmSXM - ORD
1 stop17h 14mAmerican Airlines
Deal found 10/12$385
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Wed 12/107:41 pmORD - SXM
2 stops37h 47mMultiple Airlines
Wed 12/173:15 pmSXM - ORD
1 stop10h 19mMultiple Airlines
Deal found 10/12$388
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Tue 12/97:00 amORD - SXM
2 stops26h 28mMultiple Airlines
Wed 12/173:15 pmSXM - ORD
1 stop10h 19mMultiple Airlines
Deal found 10/12$389

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 October 13, 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

Mon 1/5

6:37 pm-1:45 pm

1 stop17h 08m

Simpson Bay Princess Juliana

Wed 1/21

5:33 pm-8:22 am

2 stops16h 49m

$334

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 1/2

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Thu 1/8

1:45 pm-9:46 pm

1 stop10h 01m

$354

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 11/8

5:10 am-2:15 pm

1 stop7h 05m

Simpson Bay Princess Juliana

Sat 11/15

3:20 pm-12:27 am

1 stop11h 07m

$354

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/9

6:10 pm-12:15 pm

1 stop16h 05m

Simpson Bay Princess Juliana

Fri 1/16

4:26 pm-10:09 am

1 stop19h 43m

$354

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/9

6:10 pm-12:15 pm

1 stop16h 05m

Simpson Bay Princess Juliana

Thu 1/15

4:26 pm-10:09 am

1 stop19h 43m

$354

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 1/8

9:30 am-12:15 pm

2 stops24h 45m

Simpson Bay Princess Juliana

Fri 1/16

1:45 pm-9:35 am

2 stops21h 50m

$359

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 11/24

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Thu 11/27

4:20 pm-11:40 pm

1 stop9h 20m

$375

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 12/8

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Thu 12/18

1:45 pm-11:49 pm

1 stop12h 04m

$375

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 11/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Thu 11/27

4:20 pm-11:40 pm

1 stop9h 20m

$375

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 11/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Wed 11/26

4:20 pm-11:40 pm

1 stop9h 20m

$375

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/11

Showing 1-10 of 53 results
1
2
3
...
6

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 $312). 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 October 13, 2025.

A simple way to save on the total cost of your ticket is to fly from Illinois to St. Maarten at noon. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight in the evening.

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 6h 50m. 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 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 $128. Users have also found prices from $142 and $244 on Frontier and Air Canada, 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 $312). 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.
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
Orlando to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santo Domingo flights
LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
Newark to Punta Cana flights
John F Kennedy Intl to Punta Cana flights
Philadelphia to Luis Munoz Marin Intl flights
Dulles Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Montego Bay flights
Newark to Santo Domingo flights
Boston to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros flights
Baltimore to Luis Munoz Marin Intl flights
Newark to Oranjestad flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Atlanta to Luis Munoz Marin Intl flights
O'Hare Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Oranjestad flights
Reagan-National to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
Boston to Santo Domingo flights
Newark to Montego Bay flights
John F Kennedy Intl to Kingston flights
LaGuardia to Punta Cana flights
Tampa to Luis Munoz Marin Intl flights
John F Kennedy Intl to Port of Spain flights
LaGuardia to Santo Domingo flights
Newark to Simpson Bay flights
Atlanta to Montego Bay flights
Boston to Oranjestad flights
O'Hare Intl to Punta Cana flights
Newark to Nassau flights
Miami to Santo Domingo flights
Fort Lauderdale to Luis Munoz Marin Intl flights
LaGuardia to Oranjestad flights
Raleigh to Luis Munoz Marin Intl flights
Dulles Intl to Punta Cana flights
Fort Lauderdale to Santo Domingo flights
Miami to Luis Munoz Marin Intl flights
John F Kennedy Intl to Nassau flights
LaGuardia to Montego Bay flights
John F Kennedy Intl to Saint Thomas Island flights
John F Kennedy Intl to Simpson Bay flights
Detroit to Luis Munoz Marin Intl flights
Boston to Punta Cana flights
Orlando to Punta Cana flights
Minneapolis to Luis Munoz Marin Intl flights
LaGuardia to Santiago de los Caballeros flights

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 October 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$318Average$721FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$597Average$929FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$618Average$713FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.