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St. Maarten

$123+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SXM
dic. 23 — dic. 301
lun. 12/23
lun. 12/30
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 diciembre 18, 2024.

Round-trip from

$350
(Kiwi.com)

One-way from

$123
(Trip.com)
From Chicago (CHI) to St. Maarten
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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 diciembre 18, 2024.

This American Airlines deal was found by Cheapflights users on 12/17. 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.
mar. 12/315:00 amORD - SXM
1 stop7h 28mAmerican Airlines
mar. 1/215:19 pmSXM - ORD
1 stop9h 08mAmerican Airlines
Deal found 12/17$755
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
vie. 12/279:35 pmORD - SXM
2 stops35h 45mMultiple Airlines
lun. 12/303:25 pmSXM - ORD
1 stop30h 26mMultiple Airlines
Deal found 12/17$775
This CheapOair deal was found by Cheapflights users on 12/17. 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.
mié. 12/255:00 amORD - SXM
1 stop7h 30mSpirit Airlines
lun. 12/303:25 pmSXM - ORD
1 stop30h 26mSpirit Airlines
Deal found 12/17$872
This CheapOair deal was found by Cheapflights users on 12/17. 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.
mié. 12/2510:50 amMDW - SXM
2 stops52h 29mFrontier
lun. 12/306:29 pmSXM - MDW
2 stops22h 44mFrontier
Deal found 12/17$929
This Delta deal was found by Cheapflights users on 12/17. 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.
jue. 12/196:00 amMDW - SXM
1 stop7h 11mDelta
vie. 12/271:50 pmSXM - MDW
1 stop10h 16mDelta
Deal found 12/17$1,010
This CheapOair deal was found by Cheapflights users on 12/17. 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.
jue. 12/192:19 pmORD - SXM
2 stops25h 00mFrontier
vie. 12/276:29 pmSXM - ORD
2 stops17h 25mFrontier
Deal found 12/17$1,022
This United deal was found by Cheapflights users on 12/17. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/218:45 amORD - SXM
Nonstop5h 07mUnited Airlines
sáb. 12/282:46 pmSXM - ORD
Nonstop5h 54mUnited Airlines
Deal found 12/17$1,070
This Justfly.com deal was found by Cheapflights users on 12/17. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/208:25 pmORD - SXM
2 stops41h 30mAir Canada
mié. 12/255:15 pmSXM - ORD
2 stops19h 39mAir Canada
Deal found 12/17$1,075
This Delta deal was found by Cheapflights users on 12/18. 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.
vie. 12/205:40 amORD - SXM
1 stop7h 31mDelta
mar. 12/311:50 pmSXM - ORD
1 stop12h 06mDelta
Deal found 12/18$1,215
This Mytrip deal was found by Cheapflights users on 12/17. 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.
vie. 12/275:35 pmMDW - SXM
2 stops16h 20mMultiple Airlines
lun. 12/301:05 pmSXM - MDW
2 stops23h 15mMultiple Airlines
Deal found 12/17$1,483
This CheapOair deal was found by Cheapflights users on 12/17. 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.
dom. 12/2911:48 amMDW - SXM
2 stops25h 29mWestJet
dom. 1/54:10 pmSXM - MDW
2 stops27h 37mWestJet
Deal found 12/17$4,106
This WestJet deal was found by Cheapflights users on 12/18. 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.
vie. 12/202:50 pmORD - SXM
2 stops46h 27mWestJet
mar. 12/314:10 pmSXM - ORD
2 stops31h 20mWestJet
Deal found 12/18$4,815

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 diciembre 18, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

sáb. 2/1

1:44 pm-11:20 am

1 stop19h 36m

Simpson Bay Princess Juliana

sáb. 2/8

6:29 pm-12:51 am

1 stop8h 22m

$350

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

mié. 1/22

5:11 am-2:26 pm

1 stop7h 15m

Simpson Bay Princess Juliana

mié. 1/29

3:43 pm-11:32 pm

1 stop9h 49m

$384

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

jue. 2/13

4:13 pm-5:09 pm

2 stops22h 56m

Simpson Bay Princess Juliana

lun. 2/17

6:31 pm-3:13 pm

2 stops22h 42m

$472

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

sáb. 5/31

7:25 pm-11:07 am

1 stop14h 42m

Simpson Bay Princess Juliana

sáb. 6/14

12:15 pm-11:39 pm

1 stop12h 24m

$551

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

mar. 3/18

6:13 pm-3:15 pm

2 stops20h 02m

Simpson Bay Princess Juliana

dom. 3/23

3:55 pm-2:45 pm

1 stop23h 50m

$601

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

mié. 1/22

6:00 am-3:16 pm

1 stop7h 16m

Simpson Bay Princess Juliana

mié. 1/29

1:40 pm-10:20 pm

1 stop10h 40m

$630

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

mar. 1/14

5:10 am-2:00 pm

1 stop6h 50m

Simpson Bay Princess Juliana

mar. 1/21

5:19 pm-8:59 am

1 stop17h 40m

$630

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

sáb. 1/18

11:19 am-3:17 pm

2 stops25h 58m

Simpson Bay Princess Juliana

vie. 1/24

4:10 pm-5:47 pm

2 stops27h 37m

$750

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

vie. 1/24

6:00 am-3:16 pm

1 stop7h 16m

Simpson Bay Princess Juliana

mar. 1/28

1:40 pm-10:20 pm

1 stop10h 40m

$775

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

sáb. 3/29

11:15 am-2:16 pm

2 stops26h 01m

Simpson Bay Princess Juliana

sáb. 4/5

4:45 pm-10:20 am

1 stop18h 35m

$788

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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.

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 diciembre 18, 2024.

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 diciembre 18, 2024.
See what other customers who have flown with Spirit Airlines, Frontier and WestJet 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
8,604 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.3

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
8,604 reviews
Delta
8.0
Very good
8,604 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.3

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
9,059 reviews
Delta
8.0
Very good
8,604 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

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

WestJet
7.3
Good
2,818 reviews
Delta
8.0
Very good
8,604 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.3

Reviews

1 / 10

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
8,604 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.3

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
8,382 reviews
Delta
8.0
Very good
8,604 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.3

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 Frontier, which is currently one of the cheapest options available, starting at $123. Spirit Airlines flights start at $155 while deals on Air Canada start at $273 one-way.

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

    Looking at all options, your cheapest flight can be booked for $656. While the most popular route (Chicago O'Hare Intl - Simpson Bay Princess Juliana) can be booked for $361 on average our data indicates $1,080 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 diciembre 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$259Average$452FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$553Average$731FlexibilityNo cancel feeOn-time71%
DeltaCheapest$554Average$709FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$633Average$889FlexibilityNo cancel feeOn-time69%
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