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Saint Martin Island

$91+ Cheap flights from Chicago (CHI) to Saint Martin Island

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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Dez 21 — Dez 281
So 12/21
So 12/28
1 adult, Economy
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Cheap flight deals from Chicago to Saint Martin Island

Keep the following information in mind while searching for Chicago to Saint Martin Island flight deals. Data was last updated November 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$234
(Super.com)

One-way from

$91
(Super.com)

Popular in

December

Cheapest in

August

Average price

$706
Provider with most accurate pricing for Chicago (CHI)-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Simpson Bay Princess Juliana flights.
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From Chicago (CHI) to Saint Martin Island
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One-way flight from Chicago (CHI) to Saint Martin Island
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Highest demand for flights based on searches. 9% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Chicago to Saint Martin Island

Cheapest flights from Chicago to Saint Martin Island
Explore the most affordable flight options available from Chicago to Saint Martin Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2025.

This Super.com deal was found by Cheapflights users on 11/19. 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.
Mi 12/105:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Mi 12/173:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/19$234
This Super.com deal was found by Cheapflights users on 11/18. 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.
Mo 12/85:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Fr 12/123:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/18$257
This Spirit deal was found by Cheapflights users on 11/19. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 12/135:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Sa 12/203:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 11/19$276
This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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.
Mi 12/175:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Mi 12/243:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 11/19$290
This Priceline deal was found by Cheapflights users on 11/19. 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.
Mi 12/105:00 amORD - SXM
1 stop7h 15mMultiple Airlines
Mi 12/175:00 pmSXM - ORD
2 stops20h 18mMultiple Airlines
Deal found 11/19$313
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Do 12/181:34 pmORD - SXM
2 stops22h 41mSpirit Airlines
Mo 12/223:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 11/20$337
This Super.com deal was found by Cheapflights users on 11/20. 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.
Mi 12/245:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Sa 12/273:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 11/20$359
This Kiwi.com deal was found by Cheapflights users on 11/19. 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.
Mo 12/226:00 amORD - SXM
2 stops54h 15mMultiple Airlines
Fr 12/263:20 pmSXM - ORD
1 stop11h 10mMultiple Airlines
Deal found 11/19$363
This Delta deal was found by Cheapflights users on 11/20. 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.
Sa 12/136:00 amMDW - SXM
1 stop6h 50mDelta
Sa 12/205:22 pmSXM - MDW
1 stop17h 43mDelta
Deal found 11/20$368
This Delta deal was found by Cheapflights users on 11/19. 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.
So 12/216:00 amMDW - SXM
1 stop6h 50mDelta
Di 12/301:45 pmSXM - MDW
1 stop10h 37mDelta
Deal found 11/19$377
This Delta deal was found by Cheapflights users on 11/19. 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.
So 12/216:00 amMDW - SXM
1 stop6h 50mDelta
Mo 12/294:15 pmSXM - MDW
2 stops20h 51mDelta
Deal found 11/19$382
This Delta deal was found by Cheapflights users on 11/20. 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.
Mi 12/246:00 amMDW - SXM
1 stop6h 50mDelta
Di 12/301:45 pmSXM - MDW
1 stop10h 37mDelta
Deal found 11/20$457

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Saint Martin Island 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 November 21, 2025.
Use the filters below to find and compare flights from Chicago to Saint Martin Island that are best for you.

Fly from

Chicago

Fly to

Saint Martin Island

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Do 1/8

8:22 pm-2:14 pm

1 stop15h 52m

Simpson Bay Princess Juliana

Mo 1/12

3:09 pm-11:46 pm

1 stop10h 37m

$257

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sa 12/13

5:00 am-2:15 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Sa 12/20

3:20 pm-12:30 am

1 stop11h 10m

$276

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Do 1/8

12:48 pm-2:14 pm

1 stop23h 26m

Simpson Bay Princess Juliana

So 1/11

3:09 pm-11:22 am

1 stop22h 13m

$293

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mi 1/7

3:26 pm-2:14 pm

1 stop20h 48m

Simpson Bay Princess Juliana

Mo 1/12

3:09 pm-11:46 pm

1 stop10h 37m

$308

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

So 1/11

8:27 pm-2:14 pm

2 stops15h 47m

Simpson Bay Princess Juliana

Sa 1/17

3:09 pm-11:46 pm

1 stop10h 37m

$315

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Do 1/8

8:27 pm-2:14 pm

2 stops15h 47m

Simpson Bay Princess Juliana

Mo 1/12

3:09 pm-11:22 am

1 stop22h 13m

$324

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fr 1/9

5:32 pm-2:14 pm

1 stop18h 42m

Simpson Bay Princess Juliana

Mo 1/12

3:09 pm-11:46 pm

1 stop10h 37m

$326

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mi 1/7

4:49 pm-2:14 pm

2 stops19h 25m

Simpson Bay Princess Juliana

So 1/11

3:09 pm-11:22 am

1 stop22h 13m

$326

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fr 1/9

8:22 pm-2:14 pm

1 stop15h 52m

Simpson Bay Princess Juliana

Fr 1/16

3:09 pm-11:22 am

1 stop22h 13m

$326

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mi 1/7

4:49 pm-2:14 pm

2 stops19h 25m

Simpson Bay Princess Juliana

Mo 1/12

3:09 pm-11:46 pm

1 stop10h 37m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 36 results
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Best time to book a flight from Chicago to Saint Martin Island

Have a flexible travel schedule? Discover the best time to fly to Saint Martin Island from Chicago 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 Chicago to Saint Martin Island

What is the cheapest month to book a flight from Chicago to Saint Martin Island?

Currently, September is the cheapest month in which you can book a flight from Chicago to Saint Martin Island (average of $312). Flying from Chicago to Saint Martin Island 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 CHI to SCH?

Find hourly flight availability from Chicago to Saint Martin Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 21, 2025.

One of the essential ways to save on airfare from Chicago to Saint Martin Island is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight at noon could potentially save you up to 47% on airfare.

Reviews of airlines servicing Saint Martin Island

Get insights into the airlines that provide service to Saint Martin Island. 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 Saint Martin Island. Reviews last updated November 21, 2025.
Read through reviews of airlines operating flights from Chicago to Saint Martin Island, such as Delta, United Airlines, and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,002 reviews

Food

7.3

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,002 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,029 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,047 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,159 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Boarding

8.1

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Saint Martin Island. 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 Chicago to Saint Martin Island?

    Spirit Airlines and Delta can get you from Chicago to Saint Martin Island in just under 6h 55m. Your travel time can differ by up to 8h 57m. The distance between Chicago and Saint Martin Island is about 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 Chicago to Saint Martin Island one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $107. However, be on the lookout for offers from Frontier and Delta, as they are both options that can get you from Chicago to Saint Martin Island for a low price.

  • What are the cheapest flights from Chicago to Saint Martin Island?

    On average you can expect to pay $530 for a flight from Chicago to Saint Martin Island. The cheapest flight overall is $366 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $234.

  • Can I find deals for flights from Chicago to Saint Martin Island that include hotel bookings?

    Yes. In addition to deals on Chicago to Saint Martin Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Saint Martin Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Saint Martin Island.

  • Can I find deals for business class flights from Chicago to Saint Martin Island?

    Yes. Cheapflights offers flight deals from Chicago to Saint Martin Island 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 Chicago to Saint Martin Island?

    Currently, September is the cheapest month in which you can book a flight from Chicago to Saint Martin Island (average of $312). Flying from Chicago to Saint Martin Island 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

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Alternative routes for Chicago to Saint Martin Island

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Saint Martin Island

Discover the top 5 airlines that operate flights from Chicago to Saint Martin Island. 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 November 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$318Average$706FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$420Average$877FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$535Average$711FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$585Average$711FlexibilityNo cancel feeOn-time71%

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