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$169+ 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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
May 10 — May 171
Sun 5/10
Sun 5/17
1 adult, Economy
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Cheap 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 April 10, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 4/7. 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 4/252:42 pm
SXM
-
ORD
1 stop10h 42m
Spirit Airlines
Sun 4/265:05 am
ORD
-
SXM
1 stop7h 32m
Spirit Airlines
Deal found 4/7$239
This Trip.com deal was found by Cheapflights users on 4/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/184:00 pm
SXM
-
ORD
1 stop18h 10m
Multiple Airlines
Sat 4/257:15 pm
ORD
-
SXM
1 stop17h 22m
Multiple Airlines
Deal found 4/5$327
This FlightHub deal was found by Cheapflights users on 4/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 pm
SXM
-
ORD
1 stop16h 00m
Air Canada
Fri 8/289:50 am
ORD
-
SXM
1 stop30h 10m
Air Canada
Deal found 4/9$408
This Priceline deal was found by Cheapflights users on 4/6. 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 5/216:00 pm
SXM
-
ORD
2 stops19h 11m
Multiple Airlines
Thu 5/285:05 am
ORD
-
SXM
1 stop7h 25m
Multiple Airlines
Deal found 4/6$484
This Mytrip deal was found by Cheapflights users on 4/7. 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 4/252:42 pm
SXM
-
ORD
3 stops23h 23m
Multiple Airlines
Sun 4/264:15 pm
ORD
-
SXM
1 stop21h 40m
Multiple Airlines
Deal found 4/7$490
This Delta deal was found by Cheapflights users on 4/5. 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.
Sat 8/83:18 pm
SXM
-
MDW
1 stop7h 57m
Delta
Sat 8/156:00 am
MDW
-
SXM
1 stop6h 56m
Delta
Deal found 4/5$791
This Southwest deal was found by Cheapflights users on 4/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:25 pm
SXM
-
MDW
1 stop10h 50m
Southwest
Thu 5/289:25 pm
MDW
-
SXM
2 stops15h 05m
Southwest
Deal found 4/6$835
This Southwest deal was found by Cheapflights users on 4/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:20 pm
SXM
-
MDW
1 stop10h 15m
Southwest
Sat 4/255:15 am
MDW
-
SXM
1 stop7h 25m
Southwest
Deal found 4/5$845
This Southwest deal was found by Cheapflights users on 4/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/81:55 pm
SXM
-
MDW
1 stop8h 00m
Southwest
Sat 8/152:40 pm
MDW
-
SXM
2 stops22h 25m
Southwest
Deal found 4/5$875
This Delta deal was found by Cheapflights users on 4/5. 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.
Sat 4/181:35 pm
SXM
-
MDW
1 stop9h 53m
Delta
Sat 4/256:38 pm
MDW
-
SXM
2 stops16h 32m
Delta
Deal found 4/5$971
This Mytrip deal was found by Cheapflights users on 4/5. 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 8/86:00 pm
SXM
-
MDW
2 stops16h 08m
Multiple Airlines
Sat 8/155:59 pm
MDW
-
SXM
2 stops18h 51m
Multiple Airlines
Deal found 4/5$1,485

Find 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 April 10, 2026.

Round-trip from

$239
(Cheapflightsfares)

One-way from

$169
(Super.com)

Good one-way deal

$473 or less
From St. Maarten to Chicago (CHI)
Search Deals
One-way flight from St. Maarten to Chicago (CHI)
Search Deals
Price to beat on a one-way flight from St. Maarten to Chicago (CHI).
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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 April 10, 2026.
Use the filters below to find and compare flights from St. Maarten to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/25

2:42 pm-11:07 pm

2 stops9h 25m

Chicago O'Hare Intl

Sun 4/26

5:05 am-1:37 pm

1 stop7h 32m

$321

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 8/13

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Fri 8/28

6:21 pm-5:00 pm

2 stops21h 39m

$453

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 5/20

2:25 pm-9:55 pm

1 stop8h 30m

Chicago O'Hare Intl

Wed 5/27

5:55 am-1:30 pm

1 stop6h 35m

$570

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 5/21

6:00 pm-12:11 pm

2 stops19h 11m

Chicago O'Hare Intl

Thu 5/28

8:30 pm-11:31 am

2 stops38h 01m

$597

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 8/8

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Sat 8/15

8:40 pm-1:50 pm

1 stop16h 10m

$609

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 5/22

12:31 pm-2:16 pm

1 stop26h 45m

Chicago O'Hare Intl

Fri 5/29

10:45 am-4:10 pm

1 stop28h 25m

$615

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 5/22

2:00 pm-11:26 pm

2 stops34h 26m

Chicago O'Hare Intl

Fri 5/29

7:33 pm-1:30 pm

1 stop16h 57m

$617

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 7/2

4:46 pm-6:52 am

2 stops15h 06m

Chicago O'Hare Intl

Tue 7/7

8:54 pm-1:51 pm

1 stop15h 57m

$670
Quickest round-trip

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 8/8

3:18 pm-10:15 pm

1 stop7h 57m

Chicago Midway

Sat 8/15

6:00 am-1:56 pm

1 stop6h 56m

$791

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 5/21

2:25 pm-12:15 am

1 stop10h 50m

Chicago Midway

Thu 5/28

9:25 pm-1:30 pm

2 stops15h 05m

$835

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/5

Showing 1-10 of 27 resultsSorted by cheapest first
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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

What is the cheapest time of day to fly from SX to CHI?

Find hourly flight availability from St. Maarten to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 10, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from St. Maarten to Chicago as you normally would.

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.

  • How long is the flight from St. Maarten to Chicago?

    Airlines like Spirit Airlines, Air Canada, and Delta fly from St. Maarten to Chicago in about 7h 57m. The time it takes to get you to your destination can typically vary by up to 9h 19m. St. Maarten and Chicago are separated by a distance of 2189 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from St. Maarten to Chicago one-way?

    $163 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 American Airlines and United Airlines, with prices starting from $374 and $389, 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 $476, our data indicates the cheapest price to be $473. The most popular route (Simpson Bay Princess Juliana - Chicago O'Hare Intl), is priced around $239.

  • 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.

See more FAQs

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