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St. Maarten

$91+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Dec 25 — Jan 11
Thu 12/25
Thu 1/1
1 adult, Economy
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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 November 25, 2025.

This Super.com deal was found by Cheapflights users on 11/24. 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.
Mon 12/155:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Mon 12/223:20 pmSXM - ORD
1 stop11h 10mSpirit Airlines
Deal found 11/24$273
This Super.com deal was found by Cheapflights users on 11/24. 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.
Mon 12/85:00 amORD - SXM
1 stop7h 15mSpirit Airlines
Fri 12/123:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/24$312
This Priceline deal was found by Cheapflights users on 11/23. 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.
Wed 12/105:00 amORD - SXM
1 stop7h 15mMultiple Airlines
Tue 12/163:40 pmSXM - ORD
1 stop25h 15mMultiple Airlines
Deal found 11/23$338
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 12/73:20 pmORD - SXM
1 stop20h 55mMultiple Airlines
Sat 12/133:20 pmSXM - ORD
1 stop10h 49mMultiple Airlines
Deal found 11/24$339
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/186:00 amORD - SXM
2 stops30h 15mMultiple Airlines
Mon 12/223:20 pmSXM - ORD
1 stop11h 10mMultiple Airlines
Deal found 11/25$343
This Mytrip deal was found by Cheapflights users on 11/24. 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.
Sun 12/712:09 pmORD - SXM
3 stops24h 06mSpirit Airlines
Sat 12/133:20 pmSXM - ORD
1 stop10h 49mSpirit Airlines
Deal found 11/24$357
This Priceline deal was found by Cheapflights users on 11/24. 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 12/85:00 amORD - SXM
1 stop7h 15mMultiple Airlines
Fri 12/125:00 pmSXM - ORD
2 stops20h 18mMultiple Airlines
Deal found 11/24$361
This Mytrip deal was found by Cheapflights users on 11/25. 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.
Sat 11/296:05 pmORD - SXM
2 stops43h 55mMultiple Airlines
Wed 12/103:20 pmSXM - ORD
1 stop10h 49mMultiple Airlines
Deal found 11/25$371
This Delta deal was found by Cheapflights users on 11/23. 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.
Sun 12/76:00 amMDW - SXM
1 stop6h 28mDelta
Sat 12/133:25 pmSXM - MDW
1 stop10h 22mDelta
Deal found 11/23$571
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
Mon 12/224:15 pmMDW - SXM
1 stop21h 06mMultiple Airlines
Tue 12/301:45 pmSXM - MDW
2 stops26h 52mMultiple Airlines
Deal found 11/24$583
This Kissandfly.com deal was found by Cheapflights users on 11/23. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:00 amMDW - SXM
1 stop6h 28mKLM
Sat 12/133:25 pmSXM - MDW
1 stop10h 22mKLM
Deal found 11/23$596
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
Mon 12/224:15 pmMDW - SXM
1 stop21h 06mMultiple Airlines
Mon 12/294:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Deal found 11/24$601

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 November 25, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$257
(Super.com)

One-way from

$91
(Super.com)

Popular in

April

Cheapest in

August

Average price

$706

Good round-trip deal

$420 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. 5% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 25, 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

Thu 2/5

5:15 am-2:14 pm

1 stop6h 59m

Simpson Bay Princess Juliana

Mon 2/9

3:09 pm-11:46 pm

1 stop10h 37m

$264

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/25

5:15 am-2:14 pm

1 stop6h 59m

Simpson Bay Princess Juliana

Thu 1/29

3:09 pm-11:46 pm

1 stop10h 37m

$299

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Thu 1/29

1:55 pm-10:22 pm

1 stop10h 27m

$355

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/25

1:58 pm-2:55 pm

2 stops22h 57m

Simpson Bay Princess Juliana

Thu 1/29

4:20 pm-9:49 am

1 stop19h 29m

$360

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 12/7

1:52 pm-2:15 pm

2 stops22h 23m

Simpson Bay Princess Juliana

Sat 12/13

3:20 pm-12:09 am

1 stop10h 49m

$363

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/24

12:44 pm-2:14 pm

3 stops23h 30m

Simpson Bay Princess Juliana

Mon 2/2

3:09 pm-12:42 pm

2 stops23h 33m

$381

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/11

12:50 pm-1:35 pm

1 stop23h 45m

Simpson Bay Princess Juliana

Sat 4/18

2:40 pm-2:55 pm

1 stop25h 15m

$393

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 1/25

8:45 pm-4:00 pm

1 stop17h 15m

Simpson Bay Princess Juliana

Fri 1/30

3:09 pm-11:22 am

1 stop22h 13m

$404

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 4/12

8:20 pm-2:50 pm

1 stop17h 30m

Simpson Bay Princess Juliana

Fri 4/17

4:00 pm-9:10 am

1 stop18h 10m

$406

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 1/30

1:55 pm-10:22 pm

1 stop10h 27m

$428

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 31 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 $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 November 25, 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.

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

About 37% 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?

Saturday tends to have the lowest number of delays on this route, whereas Sunday 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 36% 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 November 25, 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
7,999 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.3

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
7,999 reviews
Delta
7.9
Good
7,999 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.3

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
9,046 reviews
Delta
7.9
Good
7,999 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.3

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
11,038 reviews
Delta
7.9
Good
7,999 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.3

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
8,158 reviews
Delta
7.9
Good
7,999 reviews

Comfort

7.9

Entertainment

7.9

Overall

7.9

Boarding

8.1

Crew

8.5

Food

7.3

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 $366. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $257 on average, our data indicates $530 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

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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 November 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$315Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$318Average$705FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$420Average$878FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$535Average$711FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$550Average$702FlexibilityNo cancel feeOn-time71%

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