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$206+ Cheap flights from St. Maarten to Chicago (CHI)

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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
1 adult, Economy
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Cheap flight deals from St. Maarten to Chicago

Keep the following information in mind while searching for St. Maarten to Chicago flight deals. Data was last updated julio 31, 2025.

Round-trip from

$336
(Flightnetwork)

One-way from

$206
(Cheapflightsfares)

Good one-way deal

$550 or less
From St. Maarten to Chicago (CHI)
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One-way flight from St. Maarten to Chicago (CHI)
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Price to beat on a one-way flight from St. Maarten to Chicago (CHI).
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Find flight deals from St. Maarten to Chicago

Cheapest flights from St. Maarten to Chicago
Explore the most affordable flight options available from St. Maarten to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 31, 2025.

This Flightnetwork deal was found by Cheapflights users on 7/30. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/223:05 pmSXM - ORD
1 stop8h 43mSpirit Airlines
lun. 9/295:05 amORD - SXM
1 stop7h 55mSpirit Airlines
Deal found 7/30$336
This Mytrip deal was found by Cheapflights users on 7/31. 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.
sáb. 8/303:05 pmSXM - ORD
1 stop9h 54mMultiple Airlines
sáb. 9/64:35 pmORD - SXM
2 stops17h 51mMultiple Airlines
Deal found 7/31$386
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/301:29 pmSXM - ORD
1 stop19h 26mJetBlue
sáb. 9/68:34 amORD - SXM
1 stop27h 41mJetBlue
Deal found 7/31$478
This Delta deal was found by Cheapflights users on 7/30. 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.
lun. 9/223:20 pmSXM - MDW
2 stops22h 08mDelta
lun. 9/296:00 amMDW - SXM
1 stop6h 50mDelta
Deal found 7/30$599
This American Airlines deal was found by Cheapflights users on 7/30. 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.
jue. 10/92:40 pmSXM - ORD
2 stops10h 13mAmerican Airlines
mié. 10/159:12 pmORD - SXM
2 stops15h 25mAmerican Airlines
Deal found 7/30$599
This Mytrip deal was found by Cheapflights users on 7/31. 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.
sáb. 9/66:10 pmSXM - MDW
3 stops24h 27mMultiple Airlines
sáb. 9/131:43 pmMDW - SXM
2 stops22h 31mMultiple Airlines
Deal found 7/31$1,440

Cheapflights Fare Finder

 
Customize your flight search to find flights from St. Maarten to Chicago 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 julio 31, 2025.
Use the filters below to find and compare flights from St. Maarten to Chicago that are best for you.

Fly from

St. Maarten

Fly to

Chicago

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

lun. 9/22

3:05 pm-10:48 pm

1 stop8h 43m

Chicago O'Hare Intl

lun. 9/29

5:05 am-2:00 pm

1 stop7h 55m

$336

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

sáb. 8/30

3:05 pm-11:59 pm

1 stop9h 54m

Chicago O'Hare Intl

sáb. 9/6

4:35 pm-11:26 am

2 stops17h 51m

$386

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

sáb. 8/30

1:29 pm-7:55 am

1 stop19h 26m

Chicago O'Hare Intl

sáb. 9/6

8:34 am-1:15 pm

1 stop27h 41m

$478

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

lun. 9/22

3:20 pm-12:28 pm

2 stops22h 08m

Chicago Midway

lun. 9/29

6:00 am-1:50 pm

1 stop6h 50m

$599

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

jue. 10/9

2:40 pm-11:53 pm

2 stops10h 13m

Chicago O'Hare Intl

mié. 10/15

9:12 pm-1:37 pm

2 stops15h 25m

$599

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

sáb. 9/6

6:10 pm-5:37 pm

3 stops24h 27m

Chicago Midway

sáb. 9/13

1:43 pm-1:14 pm

2 stops22h 31m

$1,440

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

sáb. 8/30

3:05 pm-11:59 pm

1 stop9h 54m

$206

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

sáb. 8/30

3:05 pm-6:41 pm

2 stops28h 36m

$288

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

mié. 12/24

5:00 pm-11:18 am

2 stops20h 18m

$302

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

dom. 9/14

2:35 pm-12:21 pm

1 stop22h 46m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 14 results
1
2

Best time to book a flight from St. Maarten to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from St. Maarten 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 St. Maarten to Chicago
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated julio 31, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and JetBlue from St. Maarten to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
United Airlines
7.4
Good
8,900 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
JetBlue
7.3
Good
2,914 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Air Canada
7.1
Good
9,851 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

Related info for your journey

Find useful and relevant information for your journey from St. Maarten to Chicago. 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 St. Maarten to Chicago one-way?

    $206 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on JetBlue and Air Canada, with prices starting from $293 and $343, respectively.

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

    Looking for the cheapest flight from St. Maarten to Chicago? While on average our users pay $735, our data indicates the cheapest price to be $389. The most popular route (Simpson Bay Princess Juliana - Chicago Midway), is priced around $574.

  • Can I find deals for flights from St. Maarten to Chicago that include hotel bookings?

    Yes. In addition to deals on St. Maarten to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from St. Maarten to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from St. Maarten to Chicago.

  • Can I find deals for business class flights from St. Maarten to Chicago?

    Yes. Cheapflights offers flight deals from St. Maarten to Chicago 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 St. Maarten to Chicago?

    Currently, August is the cheapest month in which you can book a flight from St. Maarten to Chicago (average of $245). Flying from St. Maarten to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Alternative routes for St. Maarten to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from St. Maarten to Chicago

Discover the top airline that operate flights from St. Maarten to Chicago. 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$554Average$680FlexibilityNo cancel feeOn-time71%

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