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 $139. Users have also found prices from $308 and $378 on Delta and American Airlines, respectively.

How far in advance should I book a flight from Illinois to St. Maarten?

Find a great deal and save up to 78% by booking at least 51 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Illinois to St. Maarten within the next two weeks, with the cheapest ticket starting at $442.

What is the cheapest month to fly from Illinois to St. Maarten?

Flights from Illinois to St. Maarten lean towards being more expensive in March. Prices are generally better when you fly from Illinois to St. Maarten in September, with the cheapest ticket starting at $369.

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.

$657+ Flights from Illinois to St. Maarten

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Cheap flight deals from Illinois to St. Maarten

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$377 (Cheapflightsfares)
One-way from	$139 (Cheapflightsfares)
Popular in	March
Cheapest in	September
Average price	$727
Good round-trip deal	$795 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. 2% potential increase in price ($17 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 2025

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Price to beat on a round-trip flight from Illinois to St. Maarten.

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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 abril 2, 2025.

vie. 4/187:47 pmORD - SXM

1 stop17h 13mSpirit Airlines

sáb. 5/33:05 pmSXM - ORD

1 stop10h 53mSpirit Airlines

Deal found 4/1

$377

sáb. 5/175:05 amORD - SXM

1 stop7h 55mMultiple Airlines

sáb. 5/2412:34 pmSXM - ORD

1 stop20h 48mMultiple Airlines

Deal found 4/1

$403

vie. 5/309:12 pmMDW - SXM

1 stop13h 12mFrontier

sáb. 6/1412:36 pmSXM - MDW

1 stop8h 41mFrontier

Deal found 4/1

$431

jue. 7/35:10 amORD - SXM

2 stops53h 18mFrontier

lun. 7/76:26 pmSXM - ORD

2 stops30h 02mFrontier

Deal found 4/1

$499

dom. 4/276:00 amSTL - SXM

1 stop7h 05mDelta

jue. 5/11:46 pmSXM - STL

1 stop10h 50mDelta

Deal found 4/1

$531

dom. 5/185:12 amSTL - SXM

1 stop7h 03mAmerican Airlines

sáb. 5/242:24 pmSXM - STL

1 stop8h 55mAmerican Airlines

Deal found 3/31

$554

vie. 4/118:25 pmORD - SXM

1 stop18h 20mAir Canada

lun. 4/144:15 pmSXM - ORD

1 stop17h 40mAir Canada

Deal found 4/1

$571

mar. 7/297:37 pmSTL - SXM

1 stop17h 24mMultiple Airlines

sáb. 8/212:36 pmSXM - STL

1 stop12h 07mMultiple Airlines

Deal found 4/1

$593

mar. 5/135:30 amORD - SXM

1 stop7h 24mDelta

mar. 5/203:19 pmSXM - ORD

1 stop9h 39mDelta

Deal found 4/1

$622

sáb. 5/37:17 pmORD - SXM

1 stop16h 57mAmerican Airlines

mié. 5/73:24 pmSXM - ORD

2 stops16h 02mAmerican Airlines

Deal found 4/1

$627

mar. 7/81:07 amORD - SXM

1 stop9h 17mCopa Airlines

dom. 7/1312:23 pmSXM - ORD

1 stop12h 57mCopa Airlines

Deal found 4/1

$783

sáb. 4/266:04 amMDW - SXM

1 stop7h 01mDelta

sáb. 5/31:46 pmSXM - MDW

1 stop9h 36mDelta

Deal found 4/1

$792

Best flights from Illinois to St. Maarten
Discover carefully curated flight deals from Illinois to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated abril 2, 2025.

vie. 4/187:47 pmORD - SXM

1 stop17h 13mSpirit Airlines

sáb. 5/33:05 pmSXM - ORD

1 stop10h 53mSpirit Airlines

Deal found 4/1

$377

sáb. 5/175:05 amORD - SXM

1 stop7h 55mMultiple Airlines

sáb. 5/2412:34 pmSXM - ORD

1 stop20h 48mMultiple Airlines

Deal found 4/1

$403

vie. 5/309:12 pmMDW - SXM

1 stop13h 12mFrontier

sáb. 6/1412:36 pmSXM - MDW

1 stop8h 41mFrontier

Deal found 4/1

$431

dom. 4/276:00 amSTL - SXM

1 stop7h 05mDelta

mié. 4/301:46 pmSXM - STL

1 stop10h 50mDelta

Deal found 4/1

$531

dom. 5/185:12 amSTL - SXM

1 stop7h 03mAmerican Airlines

sáb. 5/242:24 pmSXM - STL

1 stop8h 55mAmerican Airlines

Deal found 3/31

$554

vie. 4/118:25 pmORD - SXM

1 stop18h 20mAir Canada

lun. 4/144:15 pmSXM - ORD

1 stop17h 40mAir Canada

Deal found 4/1

$571

mar. 7/81:07 amORD - SXM

1 stop9h 17mCopa Airlines

dom. 7/1312:23 pmSXM - ORD

1 stop12h 57mCopa Airlines

Deal found 4/1

$783

mié. 5/216:00 amORD - SXM

1 stop7h 43mUnited Airlines

vie. 5/301:35 pmSXM - ORD

1 stop9h 37mUnited Airlines

Deal found 4/1

$805

sáb. 6/141:40 pmORD - SXM

2 stops22h 35mWestJet

dom. 6/222:10 pmSXM - ORD

2 stops51h 34mWestJet

Deal found 4/1

$848

jue. 7/35:10 amORD - SXM

2 stops53h 18mFrontier

lun. 7/76:26 pmSXM - ORD

2 stops30h 02mFrontier

Deal found 4/1

$499

mar. 7/297:37 pmSTL - SXM

1 stop17h 24mMultiple Airlines

sáb. 8/212:36 pmSXM - STL

1 stop12h 07mMultiple Airlines

Deal found 4/1

$593

mar. 5/135:30 amORD - SXM

1 stop7h 24mDelta

jue. 5/223:19 pmSXM - ORD

1 stop9h 39mDelta

Deal found 4/1

$622

Last-minute flights from Illinois to St. Maarten
Discover last-minute flight deals from Illinois to St. Maarten. Data last updated abril 2, 2025 and is based on user searches.

mié. 4/95:00 amORD - SXM

1 stop7h 14mAmerican Airlines

mar. 4/153:18 pmSXM - ORD

1 stop9h 36mAmerican Airlines

Deal found 4/1

$842

mié. 4/96:00 amORD - SXM

1 stop7h 43mUnited Airlines

mar. 4/151:35 pmSXM - ORD

1 stop11h 05mUnited Airlines

Deal found 4/1

$932

mié. 4/912:48 pmMDW - SXM

2 stops48h 28mWestJet

mar. 4/153:10 pmSXM - MDW

2 stops42h 57mWestJet

Deal found 4/1

$3,428

jue. 4/107:33 pmORD - SXM

1 stop17h 27mSpirit Airlines

mié. 4/163:05 pmSXM - ORD

1 stop10h 15mSpirit Airlines

Deal found 4/1

$496

jue. 4/106:15 amORD - SXM

2 stops31h 01mWestJet

mar. 4/153:10 pmSXM - ORD

2 stops49h 46mWestJet

Deal found 4/1

$2,383

vie. 4/117:05 pmORD - SXM

1 stop20h 18mMultiple Airlines

mié. 4/163:05 pmSXM - ORD

1 stop10h 15mMultiple Airlines

Deal found 4/1

$410

vie. 4/118:25 pmORD - SXM

1 stop18h 20mAir Canada

lun. 4/144:15 pmSXM - ORD

1 stop17h 40mAir Canada

Deal found 4/1

$571

vie. 4/116:00 amMDW - SXM

1 stop6h 59mDelta

mar. 4/151:46 pmSXM - MDW

1 stop9h 36mDelta

Deal found 4/1

$907

sáb. 4/125:45 amORD - SXM

1 stop7h 14mDelta

mié. 4/161:46 pmSXM - ORD

1 stop8h 04mDelta

Deal found 4/1

$907

vie. 4/187:47 pmORD - SXM

1 stop17h 13mSpirit Airlines

sáb. 5/33:05 pmSXM - ORD

1 stop10h 53mSpirit Airlines

Deal found 4/1

$377

sáb. 4/266:04 amMDW - SXM

1 stop7h 01mDelta

sáb. 5/31:46 pmSXM - MDW

1 stop9h 36mDelta

Deal found 4/1

$792

dom. 4/276:00 amSTL - SXM

1 stop7h 05mDelta

mié. 4/301:46 pmSXM - STL

1 stop10h 50mDelta

Deal found 4/1

$531

One-way flights from Illinois to St. Maarten
Search for one-way flight options from Illinois to St. Maarten. Find affordable one-way fares based on user searches. Data last updated abril 2, 2025.

vie. 4/255:36 amORD - SXM

1 stop7h 24mSpirit Airlines

Deal found 3/31

$139

sáb. 4/1911:45 amORD - SXM

2 stops22h 35mMultiple Airlines

Deal found 3/31

$233

dom. 4/1310:19 amMDW - SXM

2 stops26h 41mMultiple Airlines

Deal found 4/1

$260

lun. 5/125:30 amORD - SXM

1 stop7h 24mDelta

Deal found 4/1

$308

vie. 5/165:00 amORD - SXM

1 stop7h 15mAmerican Airlines

Deal found 4/1

$378

dom. 4/136:00 amMDW - SXM

1 stop6h 59mDelta

Deal found 4/1

$443

sáb. 4/1210:37 amORD - SXM

Nonstop5h 12mUnited Airlines

Deal found 4/1

$463

Cheapflights Fare Finder

Use the filters below to find and compare flights from Illinois to St. Maarten that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

vie. 4/18

7:47 pm-2:00 pm

1 stop17h 13m

Simpson Bay Princess Juliana

sáb. 5/3

3:05 pm-12:58 am

1 stop10h 53m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

sáb. 5/17

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

sáb. 5/24

12:34 pm-8:22 am

1 stop20h 48m

$403

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

vie. 5/30

9:12 pm-11:24 am

1 stop13h 12m

Simpson Bay Princess Juliana

sáb. 6/14

12:36 pm-8:17 pm

1 stop8h 41m

$431

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

jue. 7/3

5:10 am-11:28 am

2 stops53h 18m

Simpson Bay Princess Juliana

lun. 7/7

6:26 pm-11:28 pm

2 stops30h 02m

$499

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

dom. 4/27

6:00 am-2:05 pm

1 stop7h 05m

Simpson Bay Princess Juliana

mié. 4/30

1:46 pm-11:36 pm

1 stop10h 50m

$531

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

dom. 5/18

5:12 am-1:15 pm

1 stop7h 03m

Simpson Bay Princess Juliana

sáb. 5/24

2:24 pm-10:19 pm

1 stop8h 55m

$554

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

mar. 7/29

7:37 pm-2:01 pm

1 stop17h 24m

Simpson Bay Princess Juliana

sáb. 8/2

12:36 pm-11:43 pm

1 stop12h 07m

$593

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

mar. 5/13

5:30 am-1:54 pm

1 stop7h 24m

Simpson Bay Princess Juliana

mar. 5/20

3:19 pm-11:58 pm

1 stop9h 39m

$622

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

sáb. 5/3

7:17 pm-1:14 pm

1 stop16h 57m

Simpson Bay Princess Juliana

mié. 5/7

3:24 pm-6:26 am

2 stops16h 02m

$627

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

mar. 7/8

1:07 am-11:24 am

1 stop9h 17m

Simpson Bay Princess Juliana

dom. 7/13

12:23 pm-12:20 am

1 stop12h 57m

$783

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 25 results

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 July is currently the most expensive (average of $675). 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?

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

Peruse reviews from past customers who have flown with Delta, Copa Airlines and United Airlines from Illinois to St. Maarten to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta

8.0

Very good

7,898 reviews

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Copa Airlines

7.6

Good

1,400 reviews

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines

7.4

Good

8,616 reviews

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet

7.2

Good

2,789 reviews

Delta

8.0

Very good

7,898 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

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 $139. Users have also found prices from $308 and $378 on Delta and American Airlines, 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 July is currently the most expensive (average of $675). 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

Alternative routes for Illinois to St. Maarten

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Dulles Intl to Punta Cana flights

John F Kennedy Intl to Bridgetown flights

Atlanta to Montego Bay flights

Newark to Simpson Bay flights

LaGuardia to Montego Bay flights

John F Kennedy Intl to Saint Thomas Island flights

O'Hare Intl to Punta Cana flights

Dallas/Fort Worth to Luis Munoz Marin Intl flights

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John F Kennedy Intl to St. John's flights

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Newark to Providenciales flights

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Newark to Saint Thomas Island flights

Boston to Punta Cana flights

Hobby to Luis Munoz Marin Intl flights

Top 4 airlines flying from Illinois to St. Maarten

Airline	Cheapest	Average	Flexibility	On-time
Spirit Airlines	Cheapest$325	Average$401	FlexibilityNo cancel fee	On-time65%
Delta	Cheapest$494	Average$754	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$579	Average$765	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$610	Average$896	FlexibilityNo cancel fee	On-time69%

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$139+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Illinois to St. Maarten with Cheapflights

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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 abril 2, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Find flight deals from Illinois to St. Maarten

Cheapest flights from Illinois to St. MaartenExplore 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 abril 2, 2025.

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 abril 2, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Illinois to St. Maarten that are best for you.

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.

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?

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 abril 2, 2025.

Reviews of airlines servicing St. Maarten

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?

Can I find deals for flights from Illinois to St. Maarten that include hotel bookings?

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

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

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

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.

Top 4 airlines flying from Illinois to St. Maarten

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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 abril 2, 2025.