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$199+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$329
(Gotogate)

One-way from

$199
(Cheapflightsfares)

Good one-way deal

$389 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 September 15, 2025.

This Gotogate deal was found by Cheapflights users on 9/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:05 pmSXM - ORD
1 stop9h 40mSpirit Airlines
Fri 10/177:43 pmORD - SXM
1 stop17h 17mSpirit Airlines
Deal found 9/14$329
This Spirit deal was found by Cheapflights users on 9/13. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/64:28 pmSXM - ORD
1 stop9h 14mSpirit Airlines
Sat 12/135:05 amORD - SXM
1 stop8h 05mSpirit Airlines
Deal found 9/13$437
This Flightnetwork deal was found by Cheapflights users on 9/13. 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.
Sat 12/63:40 pmSXM - ORD
1 stop21h 38mAir Canada
Sat 12/136:05 pmORD - SXM
2 stops43h 55mAir Canada
Deal found 9/13$452
This United Airlines deal was found by Cheapflights users on 9/13. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/281:52 pmSXM - ORD
1 stop10h 42mUnited Airlines
Sun 11/28:45 amORD - SXM
Nonstop5h 12mUnited Airlines
Deal found 9/13$493
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Tue 10/283:20 pmSXM - ORD
2 stops34h 43mMultiple Airlines
Sun 11/27:43 pmORD - SXM
1 stop17h 16mMultiple Airlines
Deal found 9/13$517
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 11/64:14 pmSXM - MDW
2 stops18h 26mDelta
Wed 11/126:48 pmMDW - SXM
2 stops18h 07mDelta
Deal found 9/15$600
This Kissandfly.com deal was found by Cheapflights users on 9/15. 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 11/64:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Wed 11/1211:00 amMDW - SXM
1 stop26h 21mMultiple Airlines
Deal found 9/15$698
This Kissandfly.com deal was found by Cheapflights users on 9/13. 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.
Fri 11/284:20 pmSXM - MDW
1 stop21h 30mMultiple Airlines
Sat 11/297:02 pmMDW - SXM
2 stops42h 19mMultiple Airlines
Deal found 9/13$906
This Delta deal was found by Cheapflights users on 9/14. 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 10/113:14 pmSXM - MDW
1 stop8h 00mDelta
Fri 10/176:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/14$958
This Delta deal was found by Cheapflights users on 9/15. 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.
Sun 10/263:14 pmSXM - MDW
1 stop8h 00mDelta
Sun 11/25:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/15$978
This Kissandfly.com deal was found by Cheapflights users on 9/15. 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.
Sun 10/263:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Sun 11/211:00 amMDW - SXM
2 stops21h 50mMultiple Airlines
Deal found 9/15$1,050
This Mytrip deal was found by Cheapflights users on 9/13. 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.
Tue 10/283:20 pmSXM - MDW
2 stops22h 48mMultiple Airlines
Sun 11/29:20 amMDW - SXM
3 stops23h 30mMultiple Airlines
Deal found 9/13$1,214

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 September 15, 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

Sat 10/11

3:05 pm-11:45 pm

1 stop9h 40m

Chicago O'Hare Intl

Fri 10/17

7:43 pm-2:00 pm

1 stop17h 17m

$329

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/6

4:28 pm-11:42 pm

1 stop9h 14m

Chicago O'Hare Intl

Sat 12/13

5:05 am-3:10 pm

1 stop8h 05m

$437

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/6

3:40 pm-11:18 am

1 stop21h 38m

Chicago O'Hare Intl

Sat 12/13

6:05 pm-4:00 pm

2 stops43h 55m

$452

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 10/28

1:52 pm-11:34 pm

1 stop10h 42m

Chicago O'Hare Intl

Sun 11/2

8:45 am-3:57 pm

Nonstop5h 12m

$493

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Tue 10/28

3:20 pm-6:38 pm

3 stops28h 18m

Chicago O'Hare Intl

Sun 11/2

7:43 pm-2:59 pm

1 stop17h 16m

$522

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 12/6

4:00 pm-7:54 pm

Nonstop5h 54m

Chicago O'Hare Intl

Sat 12/13

8:05 am-3:08 pm

Nonstop5h 03m

$538

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Wed 10/1

9:17 am-10:52 am

2 stops26h 35m

Chicago O'Hare Intl

Mon 10/13

5:05 am-2:00 pm

1 stop7h 55m

$542

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 11/6

4:14 pm-8:40 am

2 stops18h 26m

Chicago Midway

Wed 11/12

6:48 pm-2:55 pm

2 stops18h 07m

$600

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/6

4:26 pm-6:34 pm

2 stops28h 08m

Chicago Midway

Tue 3/10

5:59 pm-11:15 am

2 stops16h 16m

$697

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 11/6

4:20 pm-10:05 am

1 stop19h 45m

Chicago Midway

Wed 11/12

11:00 am-3:21 pm

1 stop26h 21m

$698

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 29 results
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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 Spirit Airlines, Air Canada, and Delta fly from St. Maarten to Chicago in about 9h 40m. The time it takes to get you to your destination can typically vary by up to 11h 58m. St. Maarten and Chicago are separated by a distance of 2204 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $479, our data indicates the cheapest price to be $376. The most popular route (Simpson Bay Princess Juliana - Chicago O'Hare Intl), is priced around $319.

  • 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
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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