HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Saint Martin Island

$139+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Aug 12 — Aug 191
Tue 8/12
Tue 8/19
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Saint Martin Island with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 August 7, 2025.

Round-trip from

$282
(Cheapflightsfares)

One-way from

$109
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$637
From Chicago (CHI) to Saint Martin Island
Search Deals
One-way flight from Chicago (CHI) to Saint Martin Island
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 7, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/28:12 pmORD - SXM
1 stop16h 48mSpirit Airlines
Sat 9/63:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/5$282
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/305:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Wed 9/33:05 pmSXM - ORD
1 stop9h 54mSpirit Airlines
Deal found 8/6$314
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/85:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Mon 9/153:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/5$337
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/185:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 10/253:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 8/5$341
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/65:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 9/133:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/6$342
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.
Tue 9/210:27 amORD - SXM
2 stops20h 45mMultiple Airlines
Sat 9/63:05 pmSXM - ORD
1 stop8h 43mMultiple Airlines
Deal found 8/5$355
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/65:05 amORD - SXM
1 stop8h 05mSpirit Airlines
Sat 12/134:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Deal found 8/5$394
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/177:11 pmORD - SXM
1 stop17h 49mSpirit Airlines
Fri 10/243:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Deal found 8/6$396
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.
Fri 9/195:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Fri 9/263:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
Deal found 8/5$402
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:00 amMDW - SXM
1 stop6h 35mDelta
Thu 11/274:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 8/7$587
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/165:59 pmMDW - SXM
2 stops18h 36mDelta
Thu 11/274:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 8/7$592
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.
Fri 10/36:00 amMDW - SXM
1 stop6h 50mDelta
Fri 10/103:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 8/5$612

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 August 7, 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

Tue 9/2

8:12 pm-2:00 pm

1 stop16h 48m

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-10:48 pm

1 stop8h 43m

$282

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 8/30

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Wed 9/3

3:05 pm-11:59 pm

1 stop9h 54m

$314

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 9/8

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Mon 9/15

3:05 pm-10:48 pm

1 stop8h 43m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/18

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 10/25

3:05 pm-11:45 pm

1 stop9h 40m

$341

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/6

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 9/13

3:05 pm-10:48 pm

1 stop8h 43m

$342

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 9/2

10:27 am-8:12 am

2 stops20h 45m

Simpson Bay Princess Juliana

Sat 9/6

3:05 pm-10:48 pm

1 stop8h 43m

$355

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 12/6

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sat 12/13

4:28 pm-11:42 pm

1 stop9h 14m

$394

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 10/17

7:11 pm-2:00 pm

1 stop17h 49m

Simpson Bay Princess Juliana

Fri 10/24

3:05 pm-11:45 pm

1 stop9h 40m

$396

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/24

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Sat 1/31

4:28 pm-11:42 pm

1 stop9h 14m

$399

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 9/19

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Fri 9/26

3:05 pm-10:48 pm

1 stop8h 43m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/6

Showing 1-10 of 43 results
1
2
3
...
5

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 March is currently the most expensive (average of $653). 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 August 7, 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 August 7, 2025.
Read through reviews of airlines operating flights from Chicago to Saint Martin Island, such as Delta, American Airlines, and JetBlue. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,987 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,987 reviews
Delta
8.0
Very good
7,987 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,987 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.2
Good
2,915 reviews
Delta
8.0
Very good
7,987 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
3,002 reviews
Delta
8.0
Very good
7,987 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,051 reviews
Delta
8.0
Very good
7,987 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $139. However, be on the lookout for offers from Frontier and Delta, 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 $1,072 for a flight from Chicago to Saint Martin Island. The cheapest flight overall is $737 while the most popular route, (Chicago O'Hare Intl - Simpson Bay Princess Juliana) is currently priced at $314.

  • 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 March is currently the most expensive (average of $653). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Saint Martin Island

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
Midway to Punta Cana flights
Midway to Montego Bay flights
O'Hare Intl to Providenciales flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to George Town flights
O'Hare Intl to Castries flights
Midway to Oranjestad flights
St. Louis to Punta Cana flights
Midway to Saint Thomas Island flights
St. Louis to Montego Bay flights
St. Louis to Nassau flights
Midway to Nassau flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Kingston flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Christiansted flights
Midway to Santo Domingo flights
St. Louis to Oranjestad flights
Midway to Providenciales flights
O'Hare Intl to Port of Spain flights
Midway to Simpson Bay flights
O'Hare Intl to Santiago de los Caballeros flights
St. Louis to Simpson Bay flights
Midway to George Town flights
O'Hare Intl to St. John's flights
O'Hare Intl to Castries flights
St. Louis to Willemstad flights
O'Hare Intl to Road Town flights
Evansville to Luis Munoz Marin Intl flights
St. Louis to Castries flights
O'Hare Intl to St. George's flights
St. Louis to Georgetown flights
O'Hare Intl to Ponce flights
Midway to Castries flights
St. Louis to George Town flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Basseterre flights

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 August 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$335Average$402FlexibilityNo cancel feeOn-time65%
DeltaCheapest$564Average$721FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$618Average$714FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$654Average$901FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.