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Saint Martin Island

$143+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$345
(Cheapflightsfares)

One-way from

$143
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$642
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. 8% potential increase in price ($67 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 September 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 September 29, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/27. 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 10/275:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Fri 10/313:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Deal found 9/27$345
This CheapOair deal was found by Cheapflights users on 9/27. 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.
Fri 10/247:43 pmORD - SXM
1 stop17h 17mSpirit Airlines
Fri 10/313:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Deal found 9/27$350
This Priceline deal was found by Cheapflights users on 9/27. 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 12/65:10 amORD - SXM
1 stop8h 10mFrontier
Sat 12/134:30 pmSXM - ORD
1 stop9h 38mFrontier
Deal found 9/27$359
This Cheapflightsfares deal was found by Cheapflights users on 9/27. 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 10/185:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 10/253:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 9/27$366
This Cheapflightsfares deal was found by Cheapflights users on 9/27. 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 10/255:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Mon 10/273:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Deal found 9/27$375
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 12/45:59 pmORD - SXM
1 stop19h 11mSpirit Airlines
Mon 12/84:28 pmSXM - ORD
1 stop18h 55mSpirit Airlines
Deal found 9/28$392
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/255:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Mon 11/33:20 pmSXM - ORD
1 stop20h 27mSpirit Airlines
Deal found 9/29$393
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/285:05 amORD - SXM
2 stops29h 26mMultiple Airlines
Mon 11/33:20 pmSXM - ORD
1 stop20h 27mMultiple Airlines
Deal found 9/29$394
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/255:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Fri 10/313:05 pmSXM - ORD
1 stop10h 58mSpirit Airlines
Deal found 9/29$397
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/285:05 amORD - SXM
2 stops29h 26mMultiple Airlines
Fri 10/313:05 pmSXM - ORD
1 stop10h 58mMultiple Airlines
Deal found 9/29$399
This Delta deal was found by Cheapflights users on 9/27. 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 10/276:00 amMDW - SXM
1 stop6h 49mDelta
Fri 10/313:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 9/27$687
This Delta deal was found by Cheapflights users on 9/27. 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.
Wed 11/56:00 amMDW - SXM
1 stop6h 49mDelta
Tue 11/114:20 pmSXM - MDW
1 stop9h 20mDelta
Deal found 9/27$732

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 September 29, 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

Sat 10/18

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 10/25

3:05 pm-11:45 pm

1 stop9h 40m

$381

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/11

6:35 pm-1:52 pm

1 stop17h 17m

Simpson Bay Princess Juliana

Thu 12/18

5:33 pm-8:47 am

1 stop17h 14m

$400

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 11/10

5:00 am-2:19 pm

1 stop7h 19m

Simpson Bay Princess Juliana

Thu 11/13

3:20 pm-12:37 am

1 stop11h 17m

$425

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 10/30

6:45 am-3:45 pm

1 stop8h 00m

Simpson Bay Princess Juliana

Sat 11/1

12:26 pm-8:37 pm

1 stop9h 11m

$450

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 11/6

4:40 pm-4:22 pm

1 stop21h 42m

Simpson Bay Princess Juliana

Thu 11/13

5:24 pm-7:04 am

2 stops15h 40m

$466

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 11/10

6:45 am-4:38 pm

1 stop7h 53m

Simpson Bay Princess Juliana

Sat 11/15

1:21 pm-8:52 pm

1 stop9h 31m

$472

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/11

4:50 pm-4:00 pm

1 stop21h 10m

Simpson Bay Princess Juliana

Mon 12/15

5:00 pm-5:48 pm

1 stop26h 48m

$489

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 10/5

6:30 pm-1:37 pm

1 stop18h 07m

Simpson Bay Princess Juliana

Tue 10/7

2:40 pm-11:58 pm

1 stop10h 18m

$505

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 11/26

8:15 pm-2:40 pm

2 stops16h 25m

Simpson Bay Princess Juliana

Fri 11/28

5:00 pm-3:10 pm

1 stop24h 10m

$506

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 11/12

5:00 am-4:22 pm

2 stops9h 22m

Simpson Bay Princess Juliana

Wed 11/19

5:24 pm-7:21 am

2 stops15h 57m

$511

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/28

Showing 1-10 of 28 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 $459). Flying from Chicago to Saint Martin Island in March is currently the most expensive (average of $651). 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 September 29, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Saint Martin Island as you normally would.

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 September 29, 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
8.0
Very good
7,964 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

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!
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

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!
United Airlines
7.4
Good
8,924 reviews
Delta
8.0
Very good
7,964 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

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!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,964 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

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!
Spirit Airlines
6.3
Okay
8,056 reviews
Delta
8.0
Very good
7,964 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

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 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, American Airlines, and JetBlue can get you from Chicago to Saint Martin Island in just under 7h 55m. Your travel time can differ by up to 9h 22m. The distance between Chicago and Saint Martin Island is about 2204 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    On average you can expect to pay $559 for a flight from Chicago to Saint Martin Island. The cheapest flight overall is $243 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $351.

  • 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 $459). Flying from Chicago to Saint Martin Island in March is currently the most expensive (average of $651). 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 4 airlines flying from Chicago to Saint Martin Island

Discover the top 4 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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$318Average$721FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$619Average$715FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$634Average$914FlexibilityNo cancel feeOn-time69%

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