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Saint Martin Island

$154+ 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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$333
(Cheapflightsfares)

One-way from

$154
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$714
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. 4% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 6/25:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Mon 6/93:05 pmSXM - ORD
1 stop18h 45mSpirit Airlines
Deal found 4/30$333
This FlightHub deal was found by Cheapflights users on 5/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/65:08 pmORD - SXM
1 stop17h 15mMultiple Airlines
Sat 6/143:05 pmSXM - ORD
1 stop9h 40mMultiple Airlines
Deal found 5/1$369
This Frontier deal was found by Cheapflights users on 4/30. 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 5/309:12 pmMDW - SXM
1 stop13h 12mFrontier
Sat 6/1412:36 pmSXM - MDW
1 stop8h 41mFrontier
Deal found 4/30$411
This CheapOair deal was found by Cheapflights users on 5/1. 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.
Sat 8/25:01 amORD - SXM
2 stops11h 15mFrontier
Sat 8/96:26 pmSXM - ORD
2 stops30h 18mFrontier
Deal found 5/1$413
This American Airlines deal was found by Cheapflights users on 4/30. 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 6/106:00 amORD - SXM
1 stop8h 05mAmerican Airlines
Tue 6/172:20 pmSXM - ORD
1 stop10h 37mAmerican Airlines
Deal found 4/30$622
This JetBlue deal was found by Cheapflights users on 5/1. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/166:00 amORD - SXM
1 stop7h 41mJetBlue
Sat 8/2312:15 pmSXM - ORD
1 stop12h 10mJetBlue
Deal found 5/1$635
This Orbitz deal was found by Cheapflights users on 4/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/148:25 pmORD - SXM
1 stop17h 50mAir Canada
Sun 11/234:55 pmSXM - ORD
2 stops19h 00mAir Canada
Deal found 4/30$641
This United Airlines deal was found by Cheapflights users on 5/1. 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 11/88:45 amORD - SXM
Nonstop5h 07mUnited Airlines
Sat 11/224:55 pmSXM - ORD
1 stop8h 17mUnited Airlines
Deal found 5/1$705
This Delta deal was found by Cheapflights users on 4/30. 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 10/186:00 amORD - SXM
1 stop6h 47mDelta
Sun 10/263:15 pmSXM - ORD
1 stop9h 38mDelta
Deal found 4/30$710
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 12/46:00 amMDW - SXM
1 stop6h 35mDelta
Sat 12/134:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 4/30$1,037
This Mytrip deal was found by Cheapflights users on 5/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/29:20 amMDW - SXM
2 stops26h 40mMultiple Airlines
Mon 6/93:40 pmSXM - MDW
3 stops27h 00mMultiple Airlines
Deal found 5/1$3,432
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 12/295:04 pmMDW - SXM
2 stops20h 13mWestJet
Sun 1/44:10 pmSXM - MDW
2 stops21h 08mWestJet
Deal found 4/30$4,195

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 May 1, 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

Mon 6/2

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Mon 6/9

3:05 pm-8:50 am

1 stop18h 45m

$333

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 6/6

5:08 pm-11:23 am

1 stop17h 15m

Simpson Bay Princess Juliana

Sat 6/14

3:05 pm-11:45 pm

1 stop9h 40m

$369

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 5/30

9:12 pm-11:24 am

1 stop13h 12m

Simpson Bay Princess Juliana

Sat 6/14

12:36 pm-8:17 pm

1 stop8h 41m

$411

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 6/7

5:01 am-5:04 pm

2 stops11h 03m

Simpson Bay Princess Juliana

Sat 6/14

12:36 pm-7:09 am

1 stop19h 33m

$429

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 6/10

6:00 am-3:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Tue 6/17

2:20 pm-11:57 pm

1 stop10h 37m

$622

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 7/29

5:35 am-1:56 pm

1 stop7h 21m

Simpson Bay Princess Juliana

Sat 8/2

3:21 pm-12:09 am

1 stop9h 48m

$722

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 6/2

9:20 am-1:00 pm

2 stops26h 40m

Simpson Bay Princess Juliana

Mon 6/9

3:40 pm-5:40 pm

3 stops27h 00m

$3,432

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 6/21

5:05 am-2:00 pm

1 stop7h 55m

$154

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 6/13

9:12 pm-11:26 am

1 stop13h 14m

$215

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 6/14

8:50 pm-1:34 pm

2 stops15h 44m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 11 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 July is currently the most expensive (average of $669). 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 May 1, 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 May 1, 2025.
See what other customers who have flown with Delta, United Airlines and American 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
7,934 reviews

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

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
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

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
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

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
7,934 reviews

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

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.
Spirit Airlines
6.3
Okay
7,963 reviews
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

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.
Frontier
6.0
Okay
3,287 reviews
Delta
8.0
Very good
7,934 reviews

Crew

8.5

Overall

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Comfort

7.9

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 $154. However, be on the lookout for offers from Frontier and American Airlines, 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 $879 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 $333.

  • 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 $669). 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$325Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$554Average$775FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$606Average$715FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$647Average$896FlexibilityNo cancel feeOn-time69%

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