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St. Maarten

$124+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$391
(Cheapflightsfares)

One-way from

$124
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$670

Good round-trip deal

$666 or less

Good one-way deal

$438 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. 5% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Chicago (CHI) to St. Maarten.
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Price to beat on a one-way 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 February 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 4/265:10 amORD - SXM
1 stop7h 17mSpirit Airlines
Fri 5/22:34 pmSXM - ORD
1 stop11h 07mSpirit Airlines
Deal found 2/20$385
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 5/84:15 pmORD - SXM
2 stops23h 46mMultiple Airlines
Sun 5/1111:55 amSXM - ORD
1 stop9h 55mMultiple Airlines
Deal found 2/20$424
This Booking.com deal was found by Cheapflights users on 2/20. 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.
Fri 6/64:21 pmORD - SXM
1 stop17h 37mFrontier
Sat 6/1412:18 pmSXM - ORD
2 stops12h 50mFrontier
Deal found 2/20$470
This Frontier deal was found by Cheapflights users on 2/20. 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 stop12h 46mFrontier
Sat 6/1412:18 pmSXM - MDW
2 stops12h 37mFrontier
Deal found 2/20$474
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/236:30 pmORD - SXM
1 stop17h 25mAmerican Airlines
Thu 4/33:20 pmSXM - ORD
1 stop10h 00mAmerican Airlines
Deal found 2/20$622
This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 4/96:00 amMDW - SXM
1 stop6h 59mDelta
Tue 4/151:46 pmSXM - MDW
1 stop9h 40mDelta
Deal found 2/20$632
This Mytrip deal was found by Cheapflights users on 2/19. 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 4/1912:55 pmMDW - SXM
1 stop24h 21mMultiple Airlines
Sat 4/2612:25 pmSXM - MDW
1 stop22h 55mMultiple Airlines
Deal found 2/19$646
This Air Canada deal was found by Cheapflights users on 2/20. 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 4/196:19 pmORD - SXM
2 stops19h 31mAir Canada
Fri 4/254:15 pmSXM - ORD
2 stops19h 32mAir Canada
Deal found 2/20$694
This United Airlines deal was found by Cheapflights users on 2/19. 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 3/159:07 pmORD - SXM
1 stop14h 13mUnited Airlines
Thu 3/201:53 pmSXM - ORD
1 stop9h 07mUnited Airlines
Deal found 2/19$703
This Kissandfly.com deal was found by Cheapflights users on 2/19. 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 4/66:00 amMDW - SXM
1 stop6h 59mKLM
Sun 4/131:40 pmSXM - MDW
1 stop9h 41mKLM
Deal found 2/19$1,393
This SmartFares deal was found by Cheapflights users on 2/19. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/210:25 amMDW - SXM
2 stops26h 51mWestJet
Mon 4/143:10 pmSXM - MDW
2 stops24h 12mWestJet
Deal found 2/19$3,164

Find flights from Chicago to St. Maarten within your budget

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 February 20, 2025.

Fly from

Chicago

Fly to

St. Maarten

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/26

5:10 am-1:27 pm

1 stop7h 17m

Simpson Bay Princess Juliana

Fri 5/2

2:34 pm-12:41 am

1 stop11h 07m

$385

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 5/8

4:15 pm-5:01 pm

2 stops23h 46m

Simpson Bay Princess Juliana

Sun 5/11

11:55 am-8:50 pm

1 stop9h 55m

$424

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/23

6:30 pm-12:55 pm

1 stop17h 25m

Simpson Bay Princess Juliana

Thu 4/3

3:20 pm-12:20 am

1 stop10h 00m

$622

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 4/9

6:00 am-1:59 pm

1 stop6h 59m

Simpson Bay Princess Juliana

Tue 4/15

1:46 pm-10:26 pm

1 stop9h 40m

$632

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 4/19

12:55 pm-2:16 pm

1 stop24h 21m

Simpson Bay Princess Juliana

Sat 4/26

12:25 pm-10:20 am

1 stop22h 55m

$646

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 4/19

6:19 pm-2:50 pm

2 stops19h 31m

Simpson Bay Princess Juliana

Fri 4/25

4:15 pm-10:47 am

2 stops19h 32m

$694

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 3/15

9:07 pm-12:20 pm

1 stop14h 13m

Simpson Bay Princess Juliana

Thu 3/20

1:53 pm-10:00 pm

1 stop9h 07m

$703

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 4/27

5:30 am-2:05 pm

1 stop7h 35m

Simpson Bay Princess Juliana

Thu 5/1

1:46 pm-8:50 pm

1 stop8h 04m

$707

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 4/6

6:00 am-1:59 pm

1 stop6h 59m

Simpson Bay Princess Juliana

Sun 4/13

1:40 pm-10:21 pm

1 stop9h 41m

$1,393

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 4/2

10:25 am-2:16 pm

2 stops26h 51m

Simpson Bay Princess Juliana

Mon 4/14

3:10 pm-2:22 pm

2 stops24h 12m

$3,164

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from Chicago to St. Maarten

Get recent, data-driven insights about flights from Chicago to St. Maarten including ideal travel times, pricing trends, and more.

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 $684). 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 February 20, 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 February 20, 2025.
See what other customers who have flown with Delta, KLM 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
8,220 reviews

Crew

8.5

Comfort

8.0

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Comfort

8.0

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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.

KLM
7.8
Good
1,333 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Comfort

8.0

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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
8,766 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Comfort

8.0

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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
8,220 reviews

Crew

8.5

Comfort

8.0

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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
2,801 reviews
Delta
8.0
Very good
8,220 reviews

Crew

8.5

Comfort

8.0

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

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 $168. United Airlines flights start at $348 while deals on Delta start at $448 one-way.

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

    Looking at all options, your cheapest flight can be booked for $378. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $323 on average our data indicates $697 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 $684). 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

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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 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$319Average$438FlexibilityNo cancel feeOn-time65%
DeltaCheapest$554Average$783FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$597Average$735FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$614Average$892FlexibilityNo cancel feeOn-time69%
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