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$203+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Round-trip from

$497
(American Airlines)

One-way from

$203
(Cheapflightsfares)
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 September 29, 2025.

This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/233:00 pmSXM - ORD
Nonstop6h 00mUnited Airlines
Sun 11/308:45 amORD - SXM
Nonstop5h 12mUnited Airlines
Deal found 9/29$390
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/261:20 pmSXM - ORD
Nonstop6h 01mUnited Airlines
Sun 11/28:45 amORD - SXM
Nonstop5h 12mUnited Airlines
Deal found 9/29$436
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/235:24 pmSXM - ORD
2 stops23h 33mAmerican Airlines
Sun 11/305:00 amORD - SXM
1 stop7h 00mAmerican Airlines
Deal found 9/29$489
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2611:30 amSXM - ORD
2 stops22h 52mMultiple Airlines
Sun 11/28:28 amORD - SXM
2 stops27h 47mMultiple Airlines
Deal found 9/29$547
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/43:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Fri 10/107:43 pmORD - SXM
1 stop17h 17mSpirit Airlines
Deal found 9/28$633
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/264:45 pmSXM - ORD
1 stop29h 07mJetBlue
Sun 11/25:45 amORD - SXM
1 stop7h 53mJetBlue
Deal found 9/29$644
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/234:20 pmSXM - MDW
1 stop9h 20mDelta
Sun 11/306:00 amMDW - SXM
1 stop6h 55mDelta
Deal found 9/29$663
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/263:14 pmSXM - MDW
1 stop8h 00mDelta
Sun 11/25:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/29$883
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.
Sun 11/234:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Sun 11/307:02 pmMDW - SXM
2 stops42h 19mMultiple Airlines
Deal found 9/29$1,143

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 September 29, 2025.
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

Sun 11/23

3:00 pm-7:00 pm

Nonstop6h 00m

Chicago O'Hare Intl

Sun 11/30

8:45 am-3:57 pm

Nonstop5h 12m

$390

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 10/26

1:20 pm-6:21 pm

Nonstop6h 01m

Chicago O'Hare Intl

Sun 11/2

8:45 am-3:57 pm

Nonstop5h 12m

$436

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 11/23

5:24 pm-2:57 pm

2 stops23h 33m

Chicago O'Hare Intl

Sun 11/30

5:00 am-2:00 pm

1 stop7h 00m

$489

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 2/14

2:40 pm-6:40 pm

Nonstop6h 00m

Chicago O'Hare Intl

Sat 2/21

1:00 pm-1:50 pm

1 stop22h 50m

$537

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 10/26

11:30 am-9:22 am

2 stops22h 52m

Chicago O'Hare Intl

Sun 11/2

8:28 am-2:15 pm

2 stops27h 47m

$547

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 3/6

4:55 pm-11:12 pm

1 stop8h 17m

Chicago O'Hare Intl

Tue 3/10

9:13 pm-12:51 pm

1 stop14h 38m

$587

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 11/23

4:20 pm-11:40 pm

1 stop9h 20m

Chicago Midway

Sun 11/30

6:00 am-2:55 pm

1 stop6h 55m

$663

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/6

4:26 pm-3:25 pm

2 stops24h 59m

Chicago Midway

Tue 3/10

1:00 pm-11:15 am

2 stops21h 15m

$697

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 11/23

4:20 pm-10:05 am

1 stop19h 45m

Chicago Midway

Sun 11/30

7:02 pm-3:21 pm

2 stops42h 19m

$1,143

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/6

4:28 pm-11:42 pm

1 stop9h 14m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

Showing 1-10 of 22 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
No data available for this route at this time. Please check back soon.

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 6h. United Airlines provides one of the quickest options available for as low as $390. The distance from Saint Martin Island to Chicago is about 2204 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Saint Martin Island to Chicago one-way?

    $203 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Air Canada and WestJet, with prices starting from $262 and $605, respectively.

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

    The cheapest flight price from Saint Martin Island to Chicago is $226. On average you can expect to pay $479. The most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl), can usually be booked for $537.

  • 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.

  • What is the cheapest month to book a flight from Saint Martin Island to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Saint Martin Island to Chicago (average of $245). Flying from Saint Martin Island to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

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

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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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