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$174+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
ago. 12 — ago. 191
mar. 8/12
mar. 8/19
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 agosto 7, 2025.

Round-trip from

$321
(Priceline)

One-way from

$174
(Cheapflightsfares)
From Saint Martin Island to Chicago (CHI)
Search Deals
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 agosto 7, 2025.

This Priceline deal was found by Cheapflights users on 8/5. 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.
sáb. 9/63:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
lun. 9/225:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Deal found 8/5$321
This Spirit deal was found by Cheapflights users on 8/5. 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.
sáb. 9/133:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
sáb. 9/205:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Deal found 8/5$342
This SmartFares deal was found by Cheapflights users on 8/6. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/183:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
sáb. 11/15:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Deal found 8/6$350
This Mytrip deal was found by Cheapflights users on 8/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/63:05 pmSXM - ORD
2 stops20h 37mSpirit Airlines
sáb. 9/135:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Deal found 8/7$400
This Mytrip deal was found by Cheapflights users on 8/5. 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.
sáb. 8/303:05 pmSXM - ORD
2 stops21h 05mSpirit Airlines
sáb. 9/65:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Deal found 8/5$415
This Mytrip deal was found by Cheapflights users on 8/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/203:05 pmSXM - ORD
1 stop9h 54mSpirit Airlines
dom. 8/248:47 pmORD - SXM
2 stops16h 13mSpirit Airlines
Deal found 8/6$424
This Spirit deal was found by Cheapflights users on 8/5. 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.
sáb. 12/64:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
sáb. 12/135:05 amORD - SXM
1 stop8h 05mSpirit Airlines
Deal found 8/5$430
This Mytrip deal was found by Cheapflights users on 8/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/183:05 pmSXM - MDW
3 stops26h 45mMultiple Airlines
sáb. 11/19:20 amMDW - SXM
2 stops29h 01mMultiple Airlines
Deal found 8/6$691
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/203:21 pmSXM - MDW
2 stops18h 14mDelta
dom. 8/246:04 amMDW - SXM
1 stop6h 52mDelta
Deal found 8/6$758
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/183:14 pmSXM - MDW
1 stop8h 00mDelta
sáb. 11/16:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 8/6$888
This Delta deal was found by Cheapflights users on 8/5. 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.
sáb. 8/303:21 pmSXM - MDW
1 stop25h 02mDelta
sáb. 9/66:00 amMDW - SXM
1 stop6h 56mDelta
Deal found 8/5$913
This Delta deal was found by Cheapflights users on 8/5. 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.
sáb. 9/63:21 pmSXM - MDW
2 stops18h 14mDelta
lun. 9/226:00 amMDW - SXM
1 stop6h 50mDelta
Deal found 8/5$1,109

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 agosto 7, 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

sáb. 9/6

3:05 pm-10:48 pm

1 stop8h 43m

Chicago O'Hare Intl

lun. 9/22

5:05 am-2:00 pm

1 stop7h 55m

$321

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

sáb. 9/13

3:05 pm-10:48 pm

1 stop8h 43m

Chicago O'Hare Intl

sáb. 9/20

5:05 am-2:00 pm

1 stop7h 55m

$342

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

sáb. 10/18

3:05 pm-11:45 pm

1 stop9h 40m

Chicago O'Hare Intl

sáb. 11/1

5:05 am-2:00 pm

1 stop7h 55m

$350

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

sáb. 9/6

3:05 pm-10:42 am

2 stops20h 37m

Chicago O'Hare Intl

sáb. 9/13

5:05 am-2:00 pm

1 stop7h 55m

$400

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

sáb. 8/30

3:05 pm-11:10 am

2 stops21h 05m

Chicago O'Hare Intl

sáb. 9/6

5:05 am-2:00 pm

1 stop7h 55m

$415

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

mié. 8/20

3:05 pm-11:59 pm

1 stop9h 54m

Chicago O'Hare Intl

dom. 8/24

8:47 pm-2:00 pm

2 stops16h 13m

$424

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

sáb. 12/6

4:28 pm-11:42 pm

1 stop9h 14m

Chicago O'Hare Intl

sáb. 12/13

5:05 am-3:10 pm

1 stop8h 05m

$430

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

sáb. 10/18

3:05 pm-4:50 pm

3 stops26h 45m

Chicago Midway

sáb. 11/1

9:20 am-3:21 pm

2 stops29h 01m

$691

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

mié. 8/20

3:21 pm-8:35 am

2 stops18h 14m

Chicago Midway

dom. 8/24

6:04 am-1:56 pm

1 stop6h 52m

$758

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

sáb. 10/18

3:14 pm-10:14 pm

1 stop8h 00m

Chicago Midway

sáb. 11/1

6:00 am-1:49 pm

1 stop6h 49m

$888

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/7

Showing 1-10 of 26 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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated agosto 7, 2025.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Saint Martin Island to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,987 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,987 reviews
Delta
8.0
Very good
7,987 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,916 reviews
Delta
8.0
Very good
7,987 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,987 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
JetBlue
7.2
Good
2,915 reviews
Delta
8.0
Very good
7,987 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Air Canada
7.1
Good
9,899 reviews
Delta
8.0
Very good
7,987 reviews

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

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.

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

    The cheapest flight price from Saint Martin Island to Chicago is $389. On average you can expect to pay $634. The most popular route, (Simpson Bay Princess Juliana - Chicago O'Hare Intl), can usually be booked for $321.

  • 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
Valparaiso
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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Top airline flying from Saint Martin Island to Chicago

Discover the top airline that operate flights from Saint Martin Island to Chicago. 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 agosto 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$554Average$680FlexibilityNo cancel feeOn-time71%

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