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$147+ Cheap flights from Saint Martin Island to Chicago (CHI)

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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
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Cheap flight deals from Saint Martin Island to Chicago

Keep the following information in mind while searching for Saint Martin Island to Chicago flight deals. Data was last updated January 12, 2026.

Round-trip from

$251
(Gotogate)

One-way from

$147
(Priceline)
From Saint Martin Island to Chicago (CHI)
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One-way flight from Saint Martin Island to Chicago (CHI)
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Find flight deals from Saint Martin Island to Chicago

Cheapest flights from Saint Martin Island to Chicago
Explore the most affordable flight options available from Saint Martin Island to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 12, 2026.

This Gotogate deal was found by Cheapflights users on 1/12. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/313:10 pm
SXM
-
ORD
1 stop24h 27m
Multiple Airlines
Sat 2/75:15 am
ORD
-
SXM
1 stop7h 00m
Multiple Airlines
Deal found 1/12$251
This Flightnetwork deal was found by Cheapflights users on 1/10. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/243:10 pm
SXM
-
ORD
1 stop24h 27m
Multiple Airlines
Sat 1/315:15 am
ORD
-
SXM
1 stop6h 55m
Multiple Airlines
Deal found 1/10$257
This Cheapflightsfares deal was found by Cheapflights users on 1/9. 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 1/173:15 pm
SXM
-
ORD
1 stop10h 31m
Spirit Airlines
Sat 1/245:15 am
ORD
-
SXM
1 stop6h 55m
Spirit Airlines
Deal found 1/9$277
This Mytrip deal was found by Cheapflights users on 1/12. 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.
Sat 1/313:15 pm
SXM
-
ORD
2 stops19h 57m
Spirit Airlines
Sat 2/75:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Deal found 1/12$303
This Expedia deal was found by Cheapflights users on 1/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:20 pm
SXM
-
ORD
1 stop10h 27m
Spirit Airlines
Thu 3/55:15 am
ORD
-
SXM
1 stop7h 00m
Spirit Airlines
Deal found 1/12$310
This Expedia deal was found by Cheapflights users on 1/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/253:40 pm
SXM
-
ORD
1 stop30h 30m
Multiple Airlines
Sun 2/15:15 am
ORD
-
SXM
1 stop7h 00m
Multiple Airlines
Deal found 1/10$346
This Trip.com deal was found by Cheapflights users on 1/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/103:40 pm
SXM
-
ORD
1 stop21h 26m
Multiple Airlines
Tue 2/175:15 am
ORD
-
SXM
1 stop7h 00m
Multiple Airlines
Deal found 1/11$347
This Priceline deal was found by Cheapflights users on 1/12. 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.
Thu 2/263:20 pm
SXM
-
ORD
1 stop10h 27m
Multiple Airlines
Thu 3/52:00 pm
ORD
-
SXM
2 stops24h 00m
Multiple Airlines
Deal found 1/12$350
This Spirit deal was found by Cheapflights users on 1/9. 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.
Mon 5/112:11 pm
SXM
-
ORD
1 stop10h 30m
Spirit Airlines
Wed 5/205:15 am
ORD
-
SXM
1 stop7h 01m
Spirit Airlines
Deal found 1/9$352
This Delta deal was found by Cheapflights users on 1/11. 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 2/101:55 pm
SXM
-
MDW
1 stop10h 27m
Delta
Tue 2/176:00 am
MDW
-
SXM
1 stop6h 50m
Delta
Deal found 1/11$500
This Delta deal was found by Cheapflights users on 1/12. 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 1/311:55 pm
SXM
-
MDW
1 stop10h 27m
Delta
Sat 2/76:25 am
MDW
-
SXM
1 stop7h 38m
Delta
Deal found 1/12$560
This Delta deal was found by Cheapflights users on 1/10. 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 1/241:55 pm
SXM
-
MDW
1 stop10h 27m
Delta
Sat 1/316:25 am
MDW
-
SXM
1 stop7h 38m
Delta
Deal found 1/10$600

Cheapflights Fare Finder

 
Customize your flight search to find flights from Saint Martin Island to Chicago 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 January 12, 2026.
Use the filters below to find and compare flights from Saint Martin Island to Chicago that are best for you.

Fly from

Saint Martin Island

Fly to

Chicago

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/31

3:10 pm-1:37 pm

1 stop24h 27m

Chicago O'Hare Intl

Sat 2/7

5:15 am-2:15 pm

1 stop7h 00m

$251

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/24

3:10 pm-1:37 pm

1 stop24h 27m

Chicago O'Hare Intl

Sat 1/31

5:15 am-2:10 pm

1 stop6h 55m

$257

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 1/31

3:15 pm-9:12 am

2 stops19h 57m

Chicago O'Hare Intl

Sat 2/7

5:15 am-2:15 pm

1 stop7h 00m

$303

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 2/26

3:20 pm-11:47 pm

1 stop10h 27m

Chicago O'Hare Intl

Thu 3/5

5:15 am-2:15 pm

1 stop7h 00m

$307

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 1/25

3:40 pm-6:51 pm

1 stop29h 11m

Chicago O'Hare Intl

Sun 2/1

5:15 am-2:15 pm

1 stop7h 00m

$346

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 2/10

3:40 pm-11:06 am

1 stop21h 26m

Chicago O'Hare Intl

Tue 2/17

5:15 am-2:15 pm

1 stop7h 00m

$347

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 2/26

3:20 pm-11:47 pm

1 stop10h 27m

Chicago O'Hare Intl

Thu 3/5

6:04 pm-4:00 pm

2 stops19h 56m

$350

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 1/25

3:15 pm-11:47 am

2 stops22h 32m

Chicago O'Hare Intl

Sun 2/1

8:36 pm-2:15 pm

2 stops15h 39m

$426

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 3/28

3:41 pm-10:52 am

1 stop20h 11m

Chicago O'Hare Intl

Wed 4/1

5:15 am-1:08 pm

1 stop6h 53m

$431

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 1/31

1:55 pm-10:22 pm

1 stop10h 27m

Chicago Midway

Sat 2/7

6:25 am-4:03 pm

1 stop7h 38m

$560

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/10

Showing 1-10 of 33 results
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Best time to book a flight from Saint Martin Island to Chicago

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

What is the cheapest time of day to fly from SCH to CHI?

Find hourly flight availability from Saint Martin Island to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 12, 2026.

When flying from Saint Martin Island to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

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

    A quick flight from Saint Martin Island to Chicago can take about 10h 27m. Spirit Airlines provides one of the quickest options available for as low as $560. The distance from Saint Martin Island to Chicago is about 2189 mi. This flight may include one or multiple stops.

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

    The cheapest flight price from Saint Martin Island to Chicago is $360. On average you can expect to pay $717. The most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl), can usually be booked for $346.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Saint Martin Island to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Saint Martin Island to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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