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St. Maarten

$207+ Cheap flights from Midway (MDW) 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Midway to St. Maarten

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) 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 January 21, 2025.

Round-trip from

$507
(Priceline)

One-way from

$207
(Kiwi.com)
From Chicago Midway to St. Maarten
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One-way flight from Chicago Midway to St. Maarten
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Find flight deals from Midway to St. Maarten

Cheapest flights from Midway to St. Maarten
Explore the most affordable flight options available from Midway to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.

This Priceline deal was found by Cheapflights users on 1/20. 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 4/108:00 amMDW - SXM
2 stops32h 05mFrontier
Mon 4/146:15 pmSXM - MDW
2 stops26h 30mFrontier
Deal found 1/20$507
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Fri 2/211:05 pmMDW - SXM
1 stop21h 10mMultiple Airlines
Mon 2/246:31 pmSXM - MDW
2 stops22h 42mMultiple Airlines
Deal found 1/19$569
This Delta deal was found by Cheapflights users on 1/19. 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 3/56:00 amMDW - SXM
1 stop7h 16mDelta
Wed 3/121:40 pmSXM - MDW
1 stop9h 43mDelta
Deal found 1/19$641
This Kissandfly.com deal was found by Cheapflights users on 1/20. 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 3/66:00 amMDW - SXM
1 stop7h 16mKLM
Thu 3/131:40 pmSXM - MDW
2 stops23h 56mKLM
Deal found 1/20$1,047
This Mytrip deal was found by Cheapflights users on 1/20. 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.
Mon 2/31:26 pmMDW - SXM
2 stops23h 50mWestJet
Tue 2/114:10 pmSXM - MDW
2 stops22h 32mWestJet
Deal found 1/20$1,188

Find flights from Midway to St. Maarten within your budget

Customize your flight search to find flights from Midway 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 January 21, 2025.

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ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 4/10

8:00 am-5:05 pm

2 stops32h 05m

Simpson Bay Princess Juliana

Mon 4/14

6:15 pm-7:45 pm

2 stops26h 30m

$507

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 2/21

1:05 pm-12:15 pm

1 stop21h 10m

Simpson Bay Princess Juliana

Mon 2/24

6:31 pm-3:13 pm

2 stops22h 42m

$569

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 3/5

6:00 am-3:16 pm

1 stop7h 16m

Simpson Bay Princess Juliana

Wed 3/12

1:40 pm-10:23 pm

1 stop9h 43m

$641

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 3/6

6:00 am-3:16 pm

1 stop7h 16m

Simpson Bay Princess Juliana

Thu 3/13

1:40 pm-12:36 pm

2 stops23h 56m

$1,047

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 2/3

1:26 pm-3:16 pm

2 stops23h 50m

Simpson Bay Princess Juliana

Tue 2/11

4:10 pm-12:42 pm

2 stops22h 32m

$1,188

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 2/2

10:58 am-2:30 pm

2 stops25h 32m

$207

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 2/2

6:00 am-3:16 pm

1 stop7h 16m

$453

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 3/2

12:44 pm-3:16 pm

2 stops24h 32m

$1,591

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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

Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Midway 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 Midway to St. Maarten

Get recent, data-driven insights about flights from Midway to St. Maarten including ideal travel times, pricing trends, and more.
No data available for this route at this time. Please check back soon.

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 January 21, 2025.
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

8.0

Crew

8.6

Entertainment

7.9

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
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

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

KLM
7.8
Good
1,341 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

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

WestJet
7.2
Good
2,829 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

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

Frontier
6.1
Okay
3,443 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

8.0

Crew

8.6

Entertainment

7.9

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 Midway to St. Maarten. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway 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 Midway Airport to St. Maarten?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to St. Maarten (average of $459). Flying from Chicago Midway Airport 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 Midway to St. Maarten

See prices for flight routes from nearby airports that may be better suited for you.
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