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

$156+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
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.

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 July 1, 2025.

Round-trip from

$357
(Cheapflightsfares)

One-way from

$156
(Flightnetwork)

Popular in

March

Cheapest in

September

Average price

$695

Good round-trip deal

$707 or less
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. 5% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to St. Maarten.
Search Deals

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 July 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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 8/165:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Sat 8/233:05 pmSXM - ORD
1 stop9h 54mSpirit Airlines
Deal found 6/30$357
This Priceline deal was found by Cheapflights users on 6/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/185:05 amORD - SXM
1 stop8h 19mMultiple Airlines
Sat 11/11:58 pmSXM - ORD
1 stop24h 59mMultiple Airlines
Deal found 6/29$358
This Expedia deal was found by Cheapflights users on 6/29. 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.
Thu 7/39:12 pmMDW - SXM
2 stops19h 04mFrontier
Sat 7/56:26 pmSXM - MDW
2 stops45h 40mFrontier
Deal found 6/29$498
This Delta deal was found by Cheapflights users on 6/30. 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 11/256:00 amMDW - SXM
1 stop6h 35mDelta
Wed 12/34:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 6/30$587
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 7/179:12 pmMDW - SXM
2 stops15h 48mMultiple Airlines
Sun 7/202:10 pmSXM - MDW
1 stop19h 35mMultiple Airlines
Deal found 6/30$677
This Kissandfly.com deal was found by Cheapflights users on 6/29. 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.
Fri 8/156:04 amMDW - SXM
1 stop6h 52mKLM
Sat 8/233:21 pmSXM - MDW
2 stops18h 14mKLM
Deal found 6/29$714
This Cheapflightsfares deal was found by Cheapflights users on 7/1. 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 12/152:00 pmMDW - SXM
2 stops23h 17mWestJet
Mon 12/224:10 pmSXM - MDW
2 stops21h 08mWestJet
Deal found 7/1$3,323

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 July 1, 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

Sat 8/16

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 8/23

3:05 pm-11:59 pm

1 stop9h 54m

$357

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/18

5:05 am-2:24 pm

1 stop8h 19m

Simpson Bay Princess Juliana

Sat 11/1

1:58 pm-1:57 pm

1 stop24h 59m

$358

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 11/25

6:00 am-2:35 pm

1 stop6h 35m

Simpson Bay Princess Juliana

Wed 12/3

4:00 pm-9:44 pm

1 stop7h 44m

$587

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 7/17

9:12 pm-2:00 pm

2 stops15h 48m

Simpson Bay Princess Juliana

Sun 7/20

2:10 pm-8:45 am

1 stop19h 35m

$677

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 8/15

6:04 am-1:56 pm

1 stop6h 52m

Simpson Bay Princess Juliana

Sat 8/23

3:21 pm-8:35 am

2 stops18h 14m

$714

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 12/15

2:00 pm-3:17 pm

2 stops23h 17m

Simpson Bay Princess Juliana

Mon 12/22

4:10 pm-11:18 am

2 stops21h 08m

$3,323

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 8/14

8:12 pm-2:00 pm

1 stop16h 48m

$156

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 8/2

5:01 am-5:21 pm

2 stops11h 20m

$203

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 12/6

3:45 pm-4:00 pm

2 stops46h 15m

$229

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 12/6

7:00 am-2:21 pm

1 stop29h 21m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 17 results
1
2

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 $459). Flying from Chicago to St. Maarten in March is currently the most expensive (average of $656). 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 July 1, 2025.

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

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 July 1, 2025.
Get a feel of what it's like to fly with Delta, KLM, and Copa 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
8.0
Very good
7,974 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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
7,974 reviews
Delta
8.0
Very good
7,974 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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!
KLM
7.8
Good
1,366 reviews
Delta
8.0
Very good
7,974 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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!
Copa Airlines
7.5
Good
1,465 reviews
Delta
8.0
Very good
7,974 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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!
United Airlines
7.4
Good
8,858 reviews
Delta
8.0
Very good
7,974 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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
7.3
Good
2,919 reviews
Delta
8.0
Very good
7,974 reviews

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Crew

8.5

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 St. Maarten. 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 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 $156. Frontier flights start at $203 while deals on Air Canada start at $229 one-way.

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

    Looking at all options, your cheapest flight can be booked for $607. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $357 on average our data indicates $752 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 $459). Flying from Chicago to St. Maarten in March is currently the most expensive (average of $656). 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
O'Hare Intl to Montego Bay flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Oranjestad flights
Midway to Montego Bay flights
O'Hare Intl to Saint Thomas Island flights
Midway to Punta Cana 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 Santo Domingo flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Castries flights
St. Louis to Punta Cana flights
O'Hare Intl to Willemstad flights
O'Hare Intl to George Town flights
St. Louis to Saint Thomas Island flights
Midway to Oranjestad flights
Midway to Saint Thomas Island flights
St. Louis to Nassau flights
St. Louis to Montego Bay flights
Midway to Nassau flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Kingston flights
St. Louis to Oranjestad flights
O'Hare Intl to Port of Spain flights
Midway to Providenciales flights
Midway to Santo Domingo flights
Moline to Punta Cana flights
O'Hare Intl to Kralendijk flights
St. Louis to Willemstad flights
St. Louis to Simpson Bay flights
O'Hare Intl to St. John's flights
St. Louis to Providenciales flights
O'Hare Intl to Road Town flights
Midway to George Town flights
O'Hare Intl to Castries flights
Midway to Santiago de los Caballeros flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to St. George's flights
O'Hare Intl to Basseterre flights
St. Louis to Castries flights
St. Louis to George Town flights
Midway to Simpson Bay flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Freeport 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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$330Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$564Average$722FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$614Average$708FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$654Average$895FlexibilityNo 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.