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St. Maarten

$411+ Cheap flights from Midway (MDW) to St. Maarten

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
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Cheap flight deals from Midway to St. Maarten

Keep the following information in mind while searching for Midway to St. Maarten flight deals. Data was last updated April 30, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$411
(Frontier)

Popular in

March

Cheapest in

September

Average price

$753
Provider with most accurate pricing for Chicago (CHI)-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Simpson Bay Princess Juliana flights.
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From Chicago Midway to St. Maarten
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Highest demand for flights based on searches. 4% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 April 30, 2025.

This Frontier deal was found by Cheapflights users on 4/29. 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.
Fri 6/69:12 pmMDW - SXM
1 stop13h 11mFrontier
Sat 6/1412:36 pmSXM - MDW
1 stop8h 41mFrontier
Deal found 4/29$411
This Delta deal was found by Cheapflights users on 4/29. 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 12/46:00 amMDW - SXM
1 stop6h 35mDelta
Sat 12/134:00 pmSXM - MDW
1 stop7h 44mDelta
Deal found 4/29$942
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Mon 12/295:04 pmMDW - SXM
2 stops20h 13mWestJet
Sun 1/44:10 pmSXM - MDW
2 stops20h 49mWestJet
Deal found 4/29$4,196

Cheapflights Fare Finder

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 April 30, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to St. Maarten that are best for you.

Fly from

Midway

Fly to

St. Maarten

Route

Depart

Return

Price

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 6/6

9:12 pm-11:23 am

1 stop13h 11m

Simpson Bay Princess Juliana

Sat 6/14

12:36 pm-8:17 pm

1 stop8h 41m

$411

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to St. Maarten
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 April 30, 2025.
Frontier
6.0
Okay
3,284 reviews

Comfort

5.6

Crew

6.8

Entertainment

4.6

Overall

6.0

Boarding

6.2

Food

4.8

Reviews

1 / 20
2.0
Mediocre

Mood Happy,Mar 2025

ONT - DFW

Very bad experience. Next time not going to this flight
Frontier
6.0
Okay
3,284 reviews
Frontier
6.0
Okay
3,284 reviews

Comfort

5.6

Crew

6.8

Entertainment

4.6

Overall

6.0

Boarding

6.2

Food

4.8

Reviews

1 / 20
2.0
Mediocre

Mood Happy,Mar 2025

ONT - DFW

Very bad experience. Next time not going to this flight

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 $675). 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.

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