HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
St. Maarten

$133+ Cheap flights from Chicago (CHI) to St. Maarten

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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to St. Maarten 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.

Find flight deals from Chicago to St. Maarten

Cheapest flights from Chicago to St. Maarten
Explore the most affordable flight options available from Chicago to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2025.

This Priceline deal was found by Cheapflights users on 10/21. 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.
Mon 11/175:10 amORD - SXM
1 stop7h 05mSpirit Airlines
Fri 11/213:20 pmSXM - ORD
1 stop9h 53mSpirit Airlines
Deal found 10/21$329
This Cheapflightsfares deal was found by Cheapflights users on 10/22. 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.
Wed 12/175:05 amORD - SXM
1 stop7h 05mSpirit Airlines
Wed 12/243:15 pmSXM - ORD
1 stop11h 15mSpirit Airlines
Deal found 10/22$339
This Cheapflightsfares deal was found by Cheapflights users on 10/21. 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 12/85:05 amORD - SXM
1 stop7h 05mSpirit Airlines
Sat 12/133:15 pmSXM - ORD
1 stop11h 04mSpirit Airlines
Deal found 10/21$343
This Cheapflightsfares deal was found by Cheapflights users on 10/23. 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 11/105:10 amORD - SXM
1 stop7h 05mSpirit Airlines
Fri 11/143:20 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Deal found 10/23$344
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 12/143:20 pmORD - SXM
1 stop20h 50mMultiple Airlines
Wed 12/243:15 pmSXM - ORD
1 stop25h 47mMultiple Airlines
Deal found 10/21$356
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Thu 12/116:15 amORD - SXM
1 stop29h 55mMultiple Airlines
Wed 12/243:15 pmSXM - ORD
1 stop25h 47mMultiple Airlines
Deal found 10/21$360
This United Airlines deal was found by Cheapflights users on 10/21. 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 12/148:45 amORD - SXM
Nonstop5h 12mUnited Airlines
Sat 12/202:40 pmSXM - ORD
Nonstop6h 00mUnited Airlines
Deal found 10/21$361
This Expedia deal was found by Cheapflights users on 10/21. 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.
Sat 12/65:05 amORD - SXM
1 stop7h 05mSpirit Airlines
Sat 12/133:15 pmSXM - ORD
1 stop11h 04mSpirit Airlines
Deal found 10/21$362
This Priceline deal was found by Cheapflights users on 10/21. 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.
Mon 12/85:05 amORD - SXM
1 stop7h 05mSpirit Airlines
Mon 12/153:15 pmSXM - ORD
1 stop11h 04mSpirit Airlines
Deal found 10/21$363
This Cheapflightsfares deal was found by Cheapflights users on 10/21. 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 11/295:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Sat 12/63:15 pmSXM - ORD
1 stop11h 04mSpirit Airlines
Deal found 10/21$364
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Tue 12/93:21 pmORD - SXM
1 stop20h 49mMultiple Airlines
Wed 12/243:15 pmSXM - ORD
1 stop25h 47mMultiple Airlines
Deal found 10/21$371
This Delta deal was found by Cheapflights users on 10/22. 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 11/106:00 amMDW - SXM
1 stop6h 55mDelta
Fri 11/144:20 pmSXM - MDW
1 stop9h 20mDelta
Deal found 10/22$433

Cheap flight deals from Chicago to St. Maarten

Keep the following information in mind while searching for Chicago to St. Maarten flight deals. Data was last updated October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(Priceline)

One-way from

$133
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$719

Good round-trip deal

$553 or less
Provider with most accurate pricing for Chicago (CHI)-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Simpson Bay Princess Juliana flights.
Search Deals
From Chicago (CHI) to St. Maarten
Search Deals
One-way flight from Chicago (CHI) to St. Maarten
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to St. Maarten.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to St. Maarten 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 October 23, 2025.
Use the filters below to find and compare flights from Chicago to St. Maarten that are best for you.

Fly from

Chicago

Fly to

St. Maarten

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 11/10

5:10 am-2:15 pm

1 stop7h 05m

Simpson Bay Princess Juliana

Fri 11/14

3:20 pm-12:27 am

1 stop11h 07m

$344

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 12/14

8:45 am-3:57 pm

Nonstop5h 12m

Simpson Bay Princess Juliana

Sat 12/20

2:40 pm-6:40 pm

Nonstop6h 00m

$361

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/23

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

$389

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 11/15

8:45 am-3:57 pm

Nonstop5h 12m

Simpson Bay Princess Juliana

Sat 11/22

5:00 pm-11:43 pm

1 stop8h 43m

$425

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 11/10

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 11/14

4:20 pm-11:40 pm

1 stop9h 20m

$433

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 12/13

8:45 am-3:57 pm

Nonstop5h 12m

Simpson Bay Princess Juliana

Sun 12/21

2:20 pm-6:21 pm

Nonstop6h 01m

$471

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 1/22

2:47 pm-3:10 pm

3 stops22h 23m

Simpson Bay Princess Juliana

Mon 1/26

4:28 pm-7:13 am

2 stops16h 45m

$472

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 12/12

9:05 pm-1:50 pm

1 stop14h 45m

Simpson Bay Princess Juliana

Sat 12/20

2:40 pm-6:40 pm

Nonstop6h 00m

$475

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 12/14

8:45 am-3:57 pm

Nonstop5h 12m

Simpson Bay Princess Juliana

Tue 12/23

4:55 pm-7:47 am

1 stop16h 52m

$481

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 12/5

3:21 pm-2:10 pm

1 stop20h 49m

Simpson Bay Princess Juliana

Sun 12/7

1:45 pm-12:59 am

1 stop13h 14m

$494

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 35 results
1
2
3
4

Best time to book a flight from Chicago to St. Maarten

Have a flexible travel schedule? Discover the best time to fly to St. Maarten 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 St. Maarten

What is the cheapest month to book a flight from Chicago to St. Maarten?

Currently, September is the cheapest month in which you can book a flight from Chicago to St. Maarten (average of $312). Flying from Chicago to St. Maarten in June is currently the most expensive (average of $595). 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 SX?

Find hourly flight availability from Chicago to St. Maarten. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 23, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 47% on flights from Chicago to St. Maarten by exploring options for tickets at noon.

Reviews of airlines servicing St. Maarten

Get insights into the airlines that provide service to St. Maarten. 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 St. Maarten. Reviews last updated October 23, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Chicago to St. Maarten by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,982 reviews
Delta
7.9
Good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,995 reviews
Delta
7.9
Good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,033 reviews
Delta
7.9
Good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Spirit Airlines
6.3
Okay
8,104 reviews
Delta
7.9
Good
7,982 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

Find useful and relevant information for your journey from Chicago to St. Maarten. 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 Chicago to St. Maarten?

    Departing from Chicago to St. Maarten will take you 5h 12m. There are 2204 mi between Chicago and St. Maarten. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to St. Maarten one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $161. JetBlue flights start at $169 while deals on Delta start at $293 one-way.

  • What are the cheapest flights from Chicago to St. Maarten?

    Looking at all options, your cheapest flight can be booked for $443. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $343 on average, our data indicates $713 when flying from Chicago to St. Maarten.

  • Can I find deals for flights from Chicago to St. Maarten that include hotel bookings?

    Yes. In addition to deals on Chicago to St. Maarten flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to St. Maarten?

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

  • Can I find deals for business class flights from Chicago to St. Maarten?

    Yes. Cheapflights offers flight deals from Chicago to St. Maarten 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 St. Maarten?

    Currently, September is the cheapest month in which you can book a flight from Chicago to St. Maarten (average of $312). Flying from Chicago to St. Maarten in June is currently the most expensive (average of $595). 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 St. Maarten

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

Top 4 airlines flying from Chicago to St. Maarten

Discover the top 4 airlines that operate flights from Chicago to St. Maarten. 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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$316Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$329Average$706FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$597Average$938FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$601Average$712FlexibilityNo cancel feeOn-time71%

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.