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$226+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
Jul 7 — Jul 141
Tue 7/7
Tue 7/14
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 June 7, 2026.

This Air Canada deal was found by Cheapflights users on 6/6. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 pm
SXM
-
ORD
1 stop16h 00m
Air Canada
Fri 7/108:40 pm
ORD
-
SXM
1 stop19h 20m
Air Canada
Deal found 6/6$398
This Expedia deal was found by Cheapflights users on 6/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:42 pm
SXM
-
ORD
1 stop11h 02m
Multiple Airlines
Fri 9/119:50 am
ORD
-
SXM
1 stop30h 10m
Multiple Airlines
Deal found 6/6$427
This Expedia deal was found by Cheapflights users on 6/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:42 pm
SXM
-
ORD
1 stop11h 02m
JetBlue
Wed 9/93:00 pm
ORD
-
SXM
1 stop20h 38m
JetBlue
Deal found 6/6$433
This Air Canada deal was found by Cheapflights users on 6/3. 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 6/66:00 pm
SXM
-
ORD
2 stops19h 11m
Air Canada
Fri 6/128:20 pm
ORD
-
SXM
1 stop19h 40m
Air Canada
Deal found 6/3$503
This Expedia deal was found by Cheapflights users on 6/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/171:42 pm
SXM
-
ORD
1 stop11h 02m
Multiple Airlines
Fri 7/245:13 pm
ORD
-
SXM
1 stop17h 17m
Multiple Airlines
Deal found 6/2$513
This Frontier deal was found by Cheapflights users on 6/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:43 pm
SXM
-
ORD
1 stop11h 36m
Frontier
Fri 7/101:50 pm
ORD
-
SXM
2 stops20h 40m
Frontier
Deal found 6/7$568
This Super.com deal was found by Cheapflights users on 6/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/221:42 pm
SXM
-
ORD
1 stop11h 02m
JetBlue
Wed 7/296:30 pm
ORD
-
SXM
1 stop18h 22m
JetBlue
Deal found 6/2$582
This Delta deal was found by Cheapflights users on 6/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/23:18 pm
SXM
-
MDW
1 stop8h 18m
Delta
Wed 9/96:00 am
MDW
-
SXM
1 stop6h 56m
Delta
Deal found 6/6$656
This Delta deal was found by Cheapflights users on 6/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/23:18 pm
SXM
-
MDW
1 stop8h 18m
Delta
Sat 9/126:00 am
MDW
-
SXM
1 stop6h 50m
Delta
Deal found 6/6$661
This Delta deal was found by Cheapflights users on 6/5. 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 6/133:18 pm
SXM
-
MDW
1 stop7h 59m
Delta
Mon 6/226:00 am
MDW
-
SXM
1 stop6h 53m
Delta
Deal found 6/5$1,523
This Mytrip deal was found by Cheapflights users on 6/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:35 am
SXM
-
MDW
3 stops29h 29m
Multiple Airlines
Fri 9/115:59 pm
MDW
-
SXM
3 stops22h 01m
Multiple Airlines
Deal found 6/6$1,742
This Mytrip deal was found by Cheapflights users on 6/5. 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 7/46:00 pm
SXM
-
MDW
1 stop16h 40m
Multiple Airlines
Fri 7/101:18 pm
MDW
-
SXM
3 stops26h 42m
Multiple Airlines
Deal found 6/5$2,056

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 June 7, 2026.

Round-trip from

$398
(Air Canada)

One-way from

$226
(Super.com)
From St. Maarten to Chicago (CHI)
Search Deals
One-way flight from St. Maarten to Chicago (CHI)
Search Deals

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 June 7, 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 7/4

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Fri 7/10

8:40 pm-5:00 pm

1 stop19h 20m

$398

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 9/2

1:42 pm-11:44 pm

1 stop11h 02m

Chicago O'Hare Intl

Wed 9/9

3:00 pm-12:38 pm

1 stop20h 38m

$433
Quickest round-trip

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 9/23

3:20 pm-10:25 pm

1 stop8h 05m

Chicago Midway

Wed 9/30

6:05 am-1:50 pm

1 stop6h 45m

$656

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 9/2

3:18 pm-10:36 pm

1 stop8h 18m

Chicago Midway

Wed 9/9

6:00 am-1:56 pm

1 stop6h 56m

$656

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 7/3

3:18 pm-11:59 pm

1 stop9h 41m

Chicago O'Hare Intl

Wed 8/12

5:28 am-1:53 pm

1 stop7h 25m

$656

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 9/2

3:18 pm-10:36 pm

1 stop8h 18m

Chicago Midway

Fri 9/11

6:00 am-1:50 pm

1 stop6h 50m

$661

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 7/2

2:19 pm-12:26 am

1 stop11h 07m

Chicago O'Hare Intl

Tue 7/7

5:07 pm-12:34 pm

1 stop18h 27m

$665

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 7/2

3:50 pm-11:31 pm

1 stop8h 41m

Chicago O'Hare Intl

Tue 7/7

9:40 pm-12:33 pm

1 stop13h 53m

$665

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 9/2

9:35 am-2:04 pm

3 stops29h 29m

Chicago Midway

Fri 9/11

5:59 pm-5:00 pm

3 stops22h 01m

$1,742

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 7/4

6:00 pm-9:40 am

1 stop16h 40m

Chicago Midway

Fri 7/10

1:18 pm-5:00 pm

3 stops26h 42m

$2,056

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/6

Showing 1-10 of 23 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
No data available for this route at this time. Please check back soon.

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 Air Canada, JetBlue, and Delta fly from St. Maarten to Chicago in about 8h 18m. The time it takes to get you to your destination can typically vary by up to 7h 42m. 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.

  • 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

Traveling to a place near Chicago?

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

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