St. Maarten

$139+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Apr 7 — Apr 141
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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 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$377
(Cheapflightsfares)

One-way from

$139
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$727

Good round-trip deal

$795 or less
Provider with most accurate pricing for Chicago (CHI)-Simpson Bay Princess Juliana flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Simpson Bay Princess Juliana flights.
From Chicago (CHI) to St. Maarten
One-way flight from Chicago (CHI) to St. Maarten
Highest demand for flights based on searches. 2% potential increase in price ($17 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Average for round-trip flights in April 2025
Price to beat on a round-trip flight from Chicago (CHI) to St. Maarten.

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 2, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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.
Fri 4/187:47 pmORD - SXM
1 stop17h 13mSpirit Airlines
Sat 5/33:05 pmSXM - ORD
1 stop10h 53mSpirit Airlines
Deal found 4/1$377
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/175:05 amORD - SXM
1 stop7h 55mMultiple Airlines
Sat 5/2412:34 pmSXM - ORD
1 stop20h 48mMultiple Airlines
Deal found 4/1$403
This Frontier deal was found by Cheapflights users on 4/1. 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 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 4/1$431
This CheapOair deal was found by Cheapflights users on 4/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/35:10 amORD - SXM
2 stops53h 18mFrontier
Mon 7/76:26 pmSXM - ORD
2 stops30h 02mFrontier
Deal found 4/1$499
This Air Canada deal was found by Cheapflights users on 4/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/118:25 pmORD - SXM
1 stop18h 20mAir Canada
Mon 4/144:15 pmSXM - ORD
1 stop17h 40mAir Canada
Deal found 4/1$571
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/135:30 amORD - SXM
1 stop7h 24mDelta
Tue 5/203:19 pmSXM - ORD
1 stop9h 39mDelta
Deal found 4/1$622
This American Airlines deal was found by Cheapflights users on 4/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/37:17 pmORD - SXM
1 stop16h 57mAmerican Airlines
Wed 5/73:24 pmSXM - ORD
2 stops16h 02mAmerican Airlines
Deal found 4/1$627
This Copa Airlines deal was found by Cheapflights users on 4/1. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/81:07 amORD - SXM
1 stop9h 17mCopa Airlines
Sun 7/1312:23 pmSXM - ORD
1 stop12h 57mCopa Airlines
Deal found 4/1$783
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/266:04 amMDW - SXM
1 stop7h 01mDelta
Sat 5/31:46 pmSXM - MDW
1 stop9h 36mDelta
Deal found 4/1$792
This United Airlines deal was found by Cheapflights users on 4/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/216:00 amORD - SXM
1 stop7h 43mUnited Airlines
Fri 5/301:35 pmSXM - ORD
1 stop9h 37mUnited Airlines
Deal found 4/1$805
This Mytrip deal was found by Cheapflights users on 4/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/169:42 amMDW - SXM
3 stops27h 18mMultiple Airlines
Fri 5/233:05 pmSXM - MDW
3 stops27h 09mMultiple Airlines
Deal found 4/1$814
This WestJet deal was found by Cheapflights users on 4/1. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/181:40 pmORD - SXM
2 stops22h 35mWestJet
Sun 6/222:10 pmSXM - ORD
2 stops51h 34mWestJet
Deal found 4/1$827

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 2, 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

Fri 4/18

7:47 pm-2:00 pm

1 stop17h 13m

Simpson Bay Princess Juliana

Sat 5/3

3:05 pm-12:58 am

1 stop10h 53m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 5/17

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 5/24

12:34 pm-8:22 am

1 stop20h 48m

$403

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

$431

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 7/3

5:10 am-11:28 am

2 stops53h 18m

Simpson Bay Princess Juliana

Mon 7/7

6:26 pm-11:28 pm

2 stops30h 02m

$499

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 5/13

5:30 am-1:54 pm

1 stop7h 24m

Simpson Bay Princess Juliana

Tue 5/20

3:19 pm-11:58 pm

1 stop9h 39m

$622

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 5/3

7:17 pm-1:14 pm

1 stop16h 57m

Simpson Bay Princess Juliana

Wed 5/7

3:24 pm-6:26 am

2 stops16h 02m

$627

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 7/8

1:07 am-11:24 am

1 stop9h 17m

Simpson Bay Princess Juliana

Sun 7/13

12:23 pm-12:20 am

1 stop12h 57m

$783

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 4/26

6:04 am-2:05 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Sat 5/3

1:46 pm-10:22 pm

1 stop9h 36m

$792

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 5/21

6:00 am-2:43 pm

1 stop7h 43m

Simpson Bay Princess Juliana

Fri 5/30

1:35 pm-10:12 pm

1 stop9h 37m

$805

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 5/16

9:42 am-2:00 pm

3 stops27h 18m

Simpson Bay Princess Juliana

Fri 5/23

3:05 pm-5:14 pm

3 stops27h 09m

$814

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 21 results
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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 2, 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 2, 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.
8.0
Very good

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

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.
8.0
Very good
8.0
Very good

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

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.
8.0
Very good

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

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.
8.0
Very good

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

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.
8.0
Very good

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

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.
8.0
Very good

Crew

8.5

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Overall

8.0

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 $139. Delta flights start at $308 while deals on American Airlines start at $378 one-way.

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

    Looking at all options, your cheapest flight can be booked for $757. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $337 on average our data indicates $1,043 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

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Alternative routes for Chicago to St. Maarten

See prices for flight routes from nearby airports that may be better suited for you.

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 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$325Average$401FlexibilityNo cancel feeOn-time65%
DeltaCheapest$554Average$799FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$603Average$725FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$610Average$896FlexibilityNo cancel feeOn-time69%

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