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Saint Martin Island

$114+ 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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Mar 13 — Mar 201
Thu 3/13
Thu 3/20
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 March 8, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$375
(Cheapflightsfares)

One-way from

$119
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$864
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. 3% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 8, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 3/7. 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 4/195:36 amORD - SXM
1 stop7h 24mSpirit Airlines
Sat 4/263:05 pmSXM - ORD
1 stop10h 53mSpirit Airlines
Deal found 3/7$375
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 3/138:46 pmORD - SXM
1 stop19h 29mMultiple Airlines
Wed 3/1912:11 pmSXM - ORD
2 stops21h 55mMultiple Airlines
Deal found 3/6$497
This Frontier deal was found by Cheapflights users on 3/7. 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 6/69:12 pmMDW - SXM
1 stop13h 11mFrontier
Sat 6/1412:18 pmSXM - MDW
1 stop8h 41mFrontier
Deal found 3/7$528
This Frontier deal was found by Cheapflights users on 3/7. 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 6/611:32 amORD - SXM
2 stops22h 51mFrontier
Sat 6/1412:18 pmSXM - ORD
1 stop12h 20mFrontier
Deal found 3/7$599
This American Airlines deal was found by Cheapflights users on 3/7. 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 4/58:30 pmORD - SXM
2 stops15h 30mAmerican Airlines
Fri 4/112:14 pmSXM - ORD
1 stop10h 40mAmerican Airlines
Deal found 3/7$619
This Delta deal was found by Cheapflights users on 3/7. 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 4/96:00 amMDW - SXM
1 stop6h 59mDelta
Tue 4/151:46 pmSXM - MDW
1 stop9h 36mDelta
Deal found 3/7$622
This Delta deal was found by Cheapflights users on 3/7. 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 4/95:45 amORD - SXM
1 stop7h 14mDelta
Tue 4/151:46 pmSXM - ORD
1 stop11h 13mDelta
Deal found 3/7$622
This JetBlue Airways deal was found by Cheapflights users on 3/6. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/278:29 pmORD - SXM
1 stop15h 37mJetBlue
Thu 5/112:40 pmSXM - ORD
1 stop10h 42mJetBlue
Deal found 3/6$665
This Justfly.com deal was found by Cheapflights users on 3/7. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/288:30 pmORD - SXM
2 stops41h 20mAir Canada
Sun 4/63:55 pmSXM - ORD
2 stops27h 59mAir Canada
Deal found 3/7$679
This United Airlines deal was found by Cheapflights users on 3/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1910:37 amORD - SXM
Nonstop5h 12mUnited Airlines
Sat 4/263:55 pmSXM - ORD
1 stop8h 34mUnited Airlines
Deal found 3/7$758
This Copa Airlines deal was found by Cheapflights users on 3/6. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/21:07 amORD - SXM
1 stop9h 17mCopa Airlines
Fri 8/812:30 pmSXM - ORD
1 stop12h 52mCopa Airlines
Deal found 3/6$783
This Kissandfly.com deal was found by Cheapflights users on 3/7. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/215:59 pmMDW - SXM
2 stops19h 06mKLM
Mon 4/281:46 pmSXM - MDW
1 stop9h 36mKLM
Deal found 3/7$1,033

Find flights from Chicago to Saint Martin Island within your budget

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 March 8, 2025.

Fly from

Chicago

Fly to

Saint Martin Island

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/19

5:36 am-2:00 pm

1 stop7h 24m

Simpson Bay Princess Juliana

Sat 4/26

3:05 pm-12:58 am

1 stop10h 53m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 3/13

8:46 pm-5:15 pm

1 stop19h 29m

Simpson Bay Princess Juliana

Wed 3/19

12:11 pm-9:06 am

2 stops21h 55m

$497

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 6/6

9:12 pm-11:23 am

1 stop13h 11m

Simpson Bay Princess Juliana

Sat 6/14

12:18 pm-7:59 pm

1 stop8h 41m

$528

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/5

8:30 pm-1:00 pm

2 stops15h 30m

Simpson Bay Princess Juliana

Fri 4/11

2:14 pm-11:54 pm

1 stop10h 40m

$619

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 4/9

6:00 am-1:59 pm

1 stop6h 59m

Simpson Bay Princess Juliana

Wed 4/30

1:46 pm-10:22 pm

1 stop9h 36m

$622

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 4/9

5:45 am-1:59 pm

1 stop7h 14m

Simpson Bay Princess Juliana

Tue 4/15

1:46 pm-11:59 pm

1 stop11h 13m

$622

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 4/27

8:29 pm-1:06 pm

1 stop15h 37m

Simpson Bay Princess Juliana

Thu 5/1

12:40 pm-10:22 pm

1 stop10h 42m

$665

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 3/28

8:30 pm-2:50 pm

2 stops41h 20m

Simpson Bay Princess Juliana

Sun 4/6

3:55 pm-6:54 pm

2 stops27h 59m

$679

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/19

10:37 am-4:49 pm

Nonstop5h 12m

Simpson Bay Princess Juliana

Sat 4/26

3:55 pm-11:29 pm

1 stop8h 34m

$758

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 4/21

5:59 pm-2:05 pm

2 stops19h 06m

Simpson Bay Princess Juliana

Mon 4/28

1:46 pm-10:22 pm

1 stop9h 36m

$1,033

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

Showing 1-10 of 20 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.

Travel insights for flights from Chicago to Saint Martin Island

Get recent, data-driven insights about flights from Chicago to Saint Martin Island including ideal travel times, pricing trends, and more.

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 July is currently the most expensive (average of $682). 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 March 8, 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 March 8, 2025.
See what other customers who have flown with Delta, KLM and United Airlines 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
8,024 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

8.0

Food

7.3

Crew

8.5

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
8,024 reviews
Delta
8.0
Very good
8,024 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

8.0

Food

7.3

Crew

8.5

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.

KLM
7.8
Good
1,322 reviews
Delta
8.0
Very good
8,024 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

8.0

Food

7.3

Crew

8.5

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
8,649 reviews
Delta
8.0
Very good
8,024 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

8.0

Food

7.3

Crew

8.5

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.

JetBlue
7.3
Good
2,986 reviews
Delta
8.0
Very good
8,024 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

8.0

Food

7.3

Crew

8.5

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
8,024 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

8.0

Food

7.3

Crew

8.5

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

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 $119. However, be on the lookout for offers from Frontier and Air Canada, 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 $669 for a flight from Chicago to Saint Martin Island. The cheapest flight overall is $328 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $312.

  • 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 July is currently the most expensive (average of $682). 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 March 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$322Average$422FlexibilityNo cancel feeOn-time65%
DeltaCheapest$554Average$806FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$598Average$736FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$615Average$892FlexibilityNo cancel feeOn-time69%
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