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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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Chicago to St. Maarten

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to St. Maarten (SX0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$401
(Mytrip)

One-way from

$139
(Kiwi.com)

Good round-trip deal

$861 or less

Good one-way deal

$353 or less
From Chicago (CHI) to St. Maarten
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One-way flight from Chicago (CHI) to St. Maarten
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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 January 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/55:10 amORD - SXM
1 stop7h 18mSpirit Airlines
Wed 3/122:33 pmSXM - ORD
2 stops18h 11mSpirit Airlines
Deal found 1/20$401
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/27:13 pmORD - SXM
2 stops19h 56mMultiple Airlines
Thu 3/611:55 amSXM - ORD
1 stop9h 56mMultiple Airlines
Deal found 1/21$409
This Priceline deal was found by Cheapflights users on 1/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/108:00 amMDW - SXM
2 stops32h 05mFrontier
Mon 4/146:15 pmSXM - MDW
2 stops26h 30mFrontier
Deal found 1/20$507
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/211:05 pmMDW - SXM
1 stop21h 10mMultiple Airlines
Mon 2/246:31 pmSXM - MDW
2 stops22h 42mMultiple Airlines
Deal found 1/19$569
This Travelocity deal was found by Cheapflights users on 1/20. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/236:39 pmORD - SXM
1 stop19h 36mAir Canada
Mon 3/314:15 pmSXM - ORD
1 stop28h 20mAir Canada
Deal found 1/20$591
This Frontier deal was found by Cheapflights users on 1/20. 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 5/306:01 pmORD - SXM
2 stops15h 57mFrontier
Sat 6/1412:18 pmSXM - ORD
1 stop12h 20mFrontier
Deal found 1/20$621
This Delta deal was found by Cheapflights users on 1/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/56:00 amMDW - SXM
1 stop7h 16mDelta
Wed 3/121:40 pmSXM - MDW
1 stop9h 43mDelta
Deal found 1/19$641
This Kissandfly.com deal was found by Cheapflights users on 1/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/66:00 amMDW - SXM
1 stop7h 16mKLM
Thu 3/131:40 pmSXM - MDW
2 stops23h 56mKLM
Deal found 1/20$1,047
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/31:26 pmMDW - SXM
2 stops23h 50mWestJet
Tue 2/114:10 pmSXM - MDW
2 stops22h 32mWestJet
Deal found 1/20$1,188

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 January 21, 2025.

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Route

Depart

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Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 3/5

5:10 am-2:28 pm

1 stop7h 18m

Simpson Bay Princess Juliana

Wed 3/12

2:33 pm-7:44 am

2 stops18h 11m

$401

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/2

7:13 pm-5:09 pm

2 stops19h 56m

Simpson Bay Princess Juliana

Thu 3/6

11:55 am-7:51 pm

1 stop9h 56m

$409

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 4/10

8:00 am-5:05 pm

2 stops32h 05m

Simpson Bay Princess Juliana

Mon 4/14

6:15 pm-7:45 pm

2 stops26h 30m

$507

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 2/21

1:05 pm-12:15 pm

1 stop21h 10m

Simpson Bay Princess Juliana

Mon 2/24

6:31 pm-3:13 pm

2 stops22h 42m

$569

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/23

6:39 pm-3:15 pm

1 stop19h 36m

Simpson Bay Princess Juliana

Mon 3/31

4:15 pm-7:35 pm

1 stop28h 20m

$591

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 5/30

6:01 pm-10:58 am

2 stops15h 57m

Simpson Bay Princess Juliana

Sat 6/14

12:18 pm-11:38 pm

1 stop12h 20m

$621

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 3/5

6:00 am-3:16 pm

1 stop7h 16m

Simpson Bay Princess Juliana

Wed 3/12

1:40 pm-10:23 pm

1 stop9h 43m

$641

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 3/6

6:00 am-3:16 pm

1 stop7h 16m

Simpson Bay Princess Juliana

Thu 3/13

1:40 pm-12:36 pm

2 stops23h 56m

$1,047

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 2/3

1:26 pm-3:16 pm

2 stops23h 50m

Simpson Bay Princess Juliana

Tue 2/11

4:10 pm-12:42 pm

2 stops22h 32m

$1,188

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 3/2

2:29 pm-5:09 pm

2 stops24h 40m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 17 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.

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 January 21, 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 January 21, 2025.
See what other customers who have flown with Spirit Airlines, Air Canada and Delta 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
8,521 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

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

Delta
8.0
Very good
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

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

KLM
7.8
Good
1,341 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

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

United Airlines
7.4
Good
8,984 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

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

WestJet
7.2
Good
2,829 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

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

Air Canada
7.0
Good
8,633 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

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 $151. Air Canada flights start at $253 while deals on United Airlines start at $338 one-way.

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

    Looking at all options, your cheapest flight can be booked for $308. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $336 on average our data indicates $703 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$282Average$445FlexibilityNo cancel feeOn-time65%
DeltaCheapest$554Average$761FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$579Average$731FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$644Average$877FlexibilityNo cancel feeOn-time69%
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