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

$154+ 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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$382
(Priceline)

One-way from

$154
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$753

Good round-trip deal

$757 or less

Good one-way deal

$328 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. 3% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to St. Maarten.
Search Deals
Price to beat on a one-way 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 April 24, 2025.

This Priceline deal was found by Cheapflights users on 4/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/25:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Mon 6/93:05 pmSXM - ORD
1 stop18h 45mSpirit Airlines
Deal found 4/23$382
This CheapOair deal was found by Cheapflights users on 4/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/165:05 amORD - SXM
1 stop7h 56mMultiple Airlines
Sat 7/2612:36 pmSXM - ORD
1 stop19h 32mMultiple Airlines
Deal found 4/23$410
This Frontier deal was found by Cheapflights users on 4/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/309:12 pmMDW - SXM
1 stop13h 12mFrontier
Sat 6/1412:36 pmSXM - MDW
1 stop8h 41mFrontier
Deal found 4/23$411
This Gotogate deal was found by Cheapflights users on 4/23. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/75:01 amORD - SXM
2 stops11h 03mFrontier
Sat 6/1412:36 pmSXM - ORD
1 stop19h 33mFrontier
Deal found 4/23$432
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/116:00 amMDW - SXM
1 stop6h 35mDelta
Wed 11/194:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 4/21$622
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/255:00 amORD - SXM
1 stop8h 24mAmerican Airlines
Tue 6/32:05 pmSXM - ORD
1 stop8h 38mAmerican Airlines
Deal found 4/23$622
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/205:35 amORD - SXM
1 stop7h 25mDelta
Thu 6/263:25 pmSXM - ORD
1 stop9h 34mDelta
Deal found 4/23$647
This Air Canada deal was found by Cheapflights users on 4/23. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:20 pmORD - SXM
2 stops19h 35mAir Canada
Sat 12/135:15 pmSXM - ORD
2 stops19h 24mAir Canada
Deal found 4/23$945
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2610:37 amORD - SXM
Nonstop5h 12mUnited Airlines
Sat 5/31:35 pmSXM - ORD
1 stop11h 04mUnited Airlines
Deal found 4/23$1,023
This WestJet deal was found by Cheapflights users on 4/23. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/215:30 pmORD - SXM
2 stops18h 45mWestJet
Sun 5/252:10 pmSXM - ORD
2 stops51h 34mWestJet
Deal found 4/23$1,277
This WestJet deal was found by Cheapflights users on 4/21. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:20 amMDW - SXM
2 stops51h 57mWestJet
Fri 11/214:10 pmSXM - MDW
2 stops27h 57mWestJet
Deal found 4/21$3,464

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 April 24, 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 6/2

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Mon 6/9

3:05 pm-8:50 am

1 stop18h 45m

$382

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 7/16

5:05 am-2:01 pm

1 stop7h 56m

Simpson Bay Princess Juliana

Sat 7/26

12:36 pm-7:08 am

1 stop19h 32m

$410

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 5/30

9:12 pm-11:24 am

1 stop13h 12m

Simpson Bay Princess Juliana

Sat 6/14

12:36 pm-8:17 pm

1 stop8h 41m

$411

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 6/7

5:01 am-5:04 pm

2 stops11h 03m

Simpson Bay Princess Juliana

Sat 6/14

12:36 pm-7:09 am

1 stop19h 33m

$432

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 5/25

5:00 am-2:24 pm

1 stop8h 24m

Simpson Bay Princess Juliana

Tue 6/3

2:05 pm-9:43 pm

1 stop8h 38m

$622

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 6/20

5:35 am-2:00 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Thu 6/26

3:25 pm-11:59 pm

1 stop9h 34m

$647

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 9/13

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Sat 9/20

3:15 pm-9:44 pm

1 stop7h 29m

$710

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 5/24

6:00 am-2:43 pm

1 stop7h 43m

Simpson Bay Princess Juliana

Sat 5/31

1:35 pm-10:12 pm

1 stop9h 37m

$1,162

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 5/21

5:30 pm-1:15 pm

2 stops18h 45m

Simpson Bay Princess Juliana

Sun 5/25

2:10 pm-4:44 pm

2 stops51h 34m

$1,277

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 6/21

5:05 am-2:00 pm

1 stop7h 55m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 15 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 July is currently the most expensive (average of $675). 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 April 24, 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 April 24, 2025.
See what other customers who have flown with Delta, Copa Airlines and United Airlines from Chicago to St. Maarten 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
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Copa Airlines
7.6
Good
1,411 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,685 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
WestJet
7.2
Good
2,816 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 $154. Frontier flights start at $162 while deals on Copa Airlines start at $305 one-way.

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

    Looking at all options, your cheapest flight can be booked for $303. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $377 on average our data indicates $811 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 July is currently the most expensive (average of $675). 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
Midway to Montego Bay flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Castries flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to George Town flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Providenciales flights
Midway to Oranjestad flights
St. Louis to Punta Cana flights
St. Louis to Montego Bay flights
Midway to Nassau flights
O'Hare Intl to Puerto Plata flights
St. Louis to Saint Thomas Island flights
Midway to Saint Thomas Island flights
St. Louis to Oranjestad flights
O'Hare Intl to Kingston flights
Midway to Santo Domingo flights
O'Hare Intl to Bridgetown flights
Midway to Providenciales flights
O'Hare Intl to St. John's flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Road Town flights
St. Louis to Nassau flights
St. Louis to Castries flights
St. Louis to Providenciales flights
O'Hare Intl to Ponce flights
St. Louis to Christiansted flights
Midway to Santiago de los Caballeros flights
Midway to George Town flights
St. Louis to Willemstad flights
St. Louis to Simpson Bay flights
O'Hare Intl to Kralendijk flights
Moline to Saint Thomas Island flights
O'Hare Intl to Havana flights
St. Louis to George Town flights
Midway to Simpson Bay flights
Midway to Kingston flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to The Valley flights
Moline to Oranjestad 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$325Average$400FlexibilityNo cancel feeOn-time65%
DeltaCheapest$554Average$775FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$604Average$716FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$647Average$897FlexibilityNo 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.