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Saint Martin Island

$166+ 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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$377
(Cheapflightsfares)

One-way from

$166
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$755
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. 5% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 18, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/17. 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 8/165:05 amORD - SXM
1 stop8h 22mSpirit Airlines
Sat 8/233:32 pmSXM - ORD
1 stop9h 27mSpirit Airlines
Deal found 6/17$377
This Booking.com deal was found by Cheapflights users on 6/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/205:05 amORD - SXM
1 stop8h 19mMultiple Airlines
Sat 9/271:58 pmSXM - ORD
1 stop23h 59mMultiple Airlines
Deal found 6/16$390
This Frontier deal was found by Cheapflights users on 6/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/279:12 pmMDW - SXM
1 stop13h 14mFrontier
Sat 7/512:36 pmSXM - MDW
1 stop8h 46mFrontier
Deal found 6/17$499
This Air Canada deal was found by Cheapflights users on 6/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:25 pmORD - SXM
2 stops39h 30mAir Canada
Sat 12/135:15 pmSXM - ORD
1 stop21h 36mAir Canada
Deal found 6/16$533
This Delta deal was found by Cheapflights users on 6/17. 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 7/155:35 amORD - SXM
1 stop7h 21mDelta
Wed 7/233:21 pmSXM - ORD
1 stop9h 48mDelta
Deal found 6/17$587
This American Airlines deal was found by Cheapflights users on 6/16. 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 12/165:00 amORD - SXM
1 stop7h 15mAmerican Airlines
Fri 12/263:30 pmSXM - ORD
1 stop19h 25mAmerican Airlines
Deal found 6/16$597
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:00 amMDW - SXM
1 stop6h 35mDelta
Sat 11/224:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 6/18$682
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 7/165:20 pmMDW - SXM
1 stop18h 55mMultiple Airlines
Wed 7/233:05 pmSXM - MDW
2 stops18h 40mMultiple Airlines
Deal found 6/17$742
This WestJet deal was found by Cheapflights users on 6/17. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/247:21 pmMDW - SXM
2 stops40h 54mWestJet
Thu 7/33:10 pmSXM - MDW
2 stops31h 35mWestJet
Deal found 6/17$3,249

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 June 18, 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 8/16

5:05 am-2:27 pm

1 stop8h 22m

Simpson Bay Princess Juliana

Sat 8/23

3:32 pm-11:59 pm

1 stop9h 27m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/20

5:05 am-2:24 pm

1 stop8h 19m

Simpson Bay Princess Juliana

Sat 9/27

1:58 pm-12:57 pm

1 stop23h 59m

$390

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 12/4

8:25 pm-1:55 pm

2 stops39h 30m

Simpson Bay Princess Juliana

Sat 12/13

5:15 pm-12:51 pm

1 stop21h 36m

$533

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 7/15

5:35 am-1:56 pm

1 stop7h 21m

Simpson Bay Princess Juliana

Wed 7/23

3:21 pm-12:09 am

1 stop9h 48m

$587

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/18

6:55 pm-1:15 pm

1 stop17h 20m

Simpson Bay Princess Juliana

Sat 10/25

2:40 pm-10:34 pm

1 stop8h 54m

$612

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 11/15

6:00 am-2:35 pm

1 stop6h 35m

Simpson Bay Princess Juliana

Sat 11/22

4:00 pm-9:44 pm

1 stop7h 44m

$682

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 7/16

5:20 pm-1:15 pm

1 stop18h 55m

Simpson Bay Princess Juliana

Wed 7/23

3:05 pm-8:45 am

2 stops18h 40m

$742

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 12/3

2:00 pm-3:17 pm

2 stops47h 17m

Simpson Bay Princess Juliana

Sun 12/7

4:10 pm-9:44 pm

2 stops31h 34m

$3,413

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 8/2

5:05 am-2:00 pm

1 stop7h 55m

$166

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 10/24

8:39 am-12:25 pm

1 stop26h 46m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/18

Showing 1-10 of 16 results
1
2

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 $657). 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 June 18, 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 June 18, 2025.
See what other customers who have flown with Delta, American Airlines and WestJet from Chicago to Saint Martin Island have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

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

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

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

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

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!
WestJet
7.2
Good
2,876 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

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!
Air Canada
7.1
Good
9,572 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

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
8,066 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

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.

  • 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 $166. 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 $752 for a flight from Chicago to Saint Martin Island. The cheapest flight overall is $607 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $372.

  • 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 $657). 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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$335Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$554Average$721FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$614Average$709FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$654Average$912FlexibilityNo cancel feeOn-time69%

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