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St. Maarten

$71+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$224
(Super.com)

One-way from

$71
(Super.com)

Popular in

December

Cheapest in

February

Average price

$612

Good round-trip deal

$621 or less
Provider with most accurate pricing for Chicago (CHI)-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Simpson Bay Princess Juliana flights.
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From Chicago (CHI) to St. Maarten
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One-way flight from Chicago (CHI) to St. Maarten
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Chicago (CHI) to St. Maarten.
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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 January 8, 2026.

This Super.com deal was found by Cheapflights users on 1/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/278:16 pmORD - SXM
1 stop15h 59mSpirit Airlines
Wed 3/43:20 pmSXM - ORD
1 stop10h 27mSpirit Airlines
Deal found 1/8$224
This FlightHub deal was found by Cheapflights users on 1/8. 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.
Tue 2/175:15 amORD - SXM
1 stop7h 00mSpirit Airlines
Tue 2/243:20 pmSXM - ORD
1 stop10h 27mSpirit Airlines
Deal found 1/8$226
This Cheapflightsfares deal was found by Cheapflights users on 1/8. 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 1/245:15 amORD - SXM
1 stop6h 55mSpirit Airlines
Sat 1/313:15 pmSXM - ORD
1 stop8h 48mSpirit Airlines
Deal found 1/8$235
This Super.com deal was found by Cheapflights users on 1/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/225:15 amORD - SXM
1 stop6h 55mSpirit Airlines
Thu 1/293:15 pmSXM - ORD
1 stop10h 31mSpirit Airlines
Deal found 1/6$250
This Cheapflightsfares deal was found by Cheapflights users on 1/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/95:15 amORD - SXM
1 stop7h 00mSpirit Airlines
Wed 2/183:20 pmSXM - ORD
1 stop10h 27mSpirit Airlines
Deal found 1/7$251
This Cheapflightsfares deal was found by Cheapflights users on 1/6. 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.
Sun 1/258:43 pmORD - SXM
1 stop15h 27mSpirit Airlines
Fri 1/303:15 pmSXM - ORD
1 stop10h 31mSpirit Airlines
Deal found 1/6$252
This Cheapflightsfares deal was found by Cheapflights users on 1/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/15:15 amORD - SXM
1 stop7h 00mSpirit Airlines
Sat 2/73:20 pmSXM - ORD
1 stop10h 27mSpirit Airlines
Deal found 1/7$254
This Priceline deal was found by Cheapflights users on 1/8. 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.
Sun 2/15:15 amORD - SXM
1 stop7h 00mSpirit Airlines
Thu 2/53:20 pmSXM - ORD
1 stop10h 27mSpirit Airlines
Deal found 1/8$262
This FlightHub deal was found by Cheapflights users on 1/6. 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 1/245:15 amORD - SXM
1 stop6h 55mSpirit Airlines
Mon 2/23:20 pmSXM - ORD
1 stop10h 27mSpirit Airlines
Deal found 1/6$265
This Delta deal was found by Cheapflights users on 1/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/256:00 amMDW - SXM
1 stop6h 55mDelta
Fri 1/301:55 pmSXM - MDW
1 stop10h 27mDelta
Deal found 1/6$509
This Delta deal was found by Cheapflights users on 1/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:00 amMDW - SXM
1 stop6h 50mDelta
Fri 2/271:38 pmSXM - MDW
1 stop10h 53mDelta
Deal found 1/6$539
This Delta deal was found by Cheapflights users on 1/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/159:35 amMDW - SXM
2 stops24h 54mDelta
Fri 3/203:20 pmSXM - MDW
2 stops22h 09mDelta
Deal found 1/6$558

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 January 8, 2026.
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 2/16

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Fri 2/20

3:20 pm-11:47 pm

1 stop10h 27m

$266

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/30

8:43 pm-2:10 pm

1 stop15h 27m

Simpson Bay Princess Juliana

Sun 2/1

3:20 pm-11:47 pm

1 stop10h 27m

$305

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/1

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Sun 2/8

3:20 pm-11:47 pm

1 stop10h 27m

$325

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 2/8

5:15 am-2:15 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Tue 2/10

5:00 pm-8:05 am

2 stops17h 05m

$378

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 5/4

5:15 am-1:16 pm

1 stop7h 01m

Simpson Bay Princess Juliana

Fri 5/8

2:11 pm-2:41 pm

2 stops25h 30m

$379

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 2/28

8:16 pm-2:15 pm

1 stop15h 59m

Simpson Bay Princess Juliana

Sat 3/7

3:20 pm-11:47 pm

1 stop10h 27m

$382

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 2/27

3:11 pm-2:15 pm

2 stops21h 04m

Simpson Bay Princess Juliana

Thu 3/5

3:20 pm-11:05 pm

1 stop9h 45m

$383

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 5/27

5:32 pm-1:16 pm

1 stop18h 44m

Simpson Bay Princess Juliana

Wed 6/3

2:11 pm-11:41 pm

1 stop10h 30m

$384

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 1/19

10:35 am-2:40 pm

1 stop26h 05m

Simpson Bay Princess Juliana

Thu 1/22

3:40 pm-2:55 pm

1 stop25h 15m

$428

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 1/19

8:45 pm-2:40 pm

2 stops15h 55m

Simpson Bay Princess Juliana

Wed 1/28

9:35 am-11:46 pm

3 stops16h 11m

$447

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 43 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, February is the cheapest month in which you can book a flight from Chicago to St. Maarten (average of $251). 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 January 8, 2026.

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.

How often are flights from Chicago to St. Maarten delayed?

About 34% of weekly flights between Chicago and St. Maarten have experienced delays in the past year, with the average delay time being 129 minutes.

What is the most punctual flight time for Chicago to St. Maarten flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Sunday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to St. Maarten flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 33% of flights being delayed.

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 January 8, 2026.
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
8,026 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,026 reviews
Delta
7.9
Good
8,026 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,139 reviews
Delta
7.9
Good
8,026 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,097 reviews
Delta
7.9
Good
8,026 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,288 reviews
Delta
7.9
Good
8,026 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.7
Fair
3,061 reviews
Delta
7.9
Good
8,026 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 6h 55m. There are 2189 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 flights from Chicago to St. Maarten?

    Looking at all options, your cheapest flight can be booked for $370. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $224 on average, our data indicates $728 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, February is the cheapest month in which you can book a flight from Chicago to St. Maarten (average of $251). 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

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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.
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Top 5 airlines flying from Chicago to St. Maarten

Discover the top 5 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$289Average$397FlexibilityNo cancel feeOn-time65%
DeltaCheapest$292Average$642FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$410Average$773FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$514Average$695FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$535Average$731FlexibilityNo cancel feeOn-time62%

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