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Cheap flights from Midway (MDW) to St. Maarten from $352

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. Click the price to replicate the search for this deal.
MDW — SXM
May 23 — May 301
From?
To?
Thu 5/23
Thu 5/30
1 adult, Economy
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How far in advance should I book a flight from Chicago Midway Airport to St. Maarten?

Travelers have found it’s best to book a flight 55 days in advance to save up to 550% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 55 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago Midway Airport to St. Maarten 1-2 weeks in advance for as low as $464, or $841 for flights within the next 24 hours.

What is the cheapest month to fly from Chicago Midway Airport to St. Maarten?

Due to multiple factors, expect to potentially pay more when booking in July. For low rates, September can be a great choice for travel to St. Maarten. Flights to St. Maarten from Chicago Midway Airport in September are about $739 on average during September, but can be found for as low as $481.

When is the cheapest time to fly from Chicago Midway Airport to St. Maarten (MDW - SX)?

When flying from Chicago Midway Airport to St. Maarten, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap Delta flights from Midway to St. Maarten

Explore cheap flight options specifically provided by Delta for the route between Midway and St. Maarten. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,634,509 searches. Data last updated May 18, 2024.
Tue 7/236:55 pmMDW - SXM
1 stop17h 50mDelta
Sat 8/173:19 pmSXM - MDW
2 stops18h 25mDelta
Deal found 5/18$584
Tue 7/236:55 pmMDW - SXM
1 stop17h 50mDelta
Sat 8/173:19 pmSXM - MDW
1 stop21h 34mDelta
Deal found 5/18$810
Tue 6/256:00 amMDW - SXM
1 stop6h 55mDelta
Tue 7/23:20 pmSXM - MDW
2 stops18h 29mDelta
Deal found 5/16$824
Tue 6/256:00 amMDW - SXM
1 stop6h 55mDelta
Tue 7/23:20 pmSXM - MDW
1 stop21h 35mDelta
Deal found 5/16$893
Mon 7/226:55 pmMDW - SXM
1 stop17h 50mDelta
Sat 7/273:10 pmSXM - MDW
1 stop19h 16mDelta
Deal found 5/17$895
Wed 11/66:15 pmMDW - SXM
1 stop18h 34mDelta
Wed 11/134:14 pmSXM - MDW
2 stops18h 31mDelta
Deal found 5/17$897
Wed 11/66:15 pmMDW - SXM
1 stop18h 34mDelta
Wed 11/134:14 pmSXM - MDW
1 stop19h 03mDelta
Deal found 5/17$898
Tue 6/46:00 amMDW - SXM
1 stop6h 40mDelta
Wed 6/53:10 pmSXM - MDW
1 stop17h 45mDelta
Deal found 5/17$905
Fri 10/116:00 amMDW - SXM
1 stop6h 49mDelta
Fri 10/183:19 pmSXM - MDW
2 stops18h 26mDelta
Deal found 5/17$908

Cheap Midway to St. Maarten flights in May & June 2024

Find cheap flight options from Midway to St. Maarten specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,634,509 searches. Prices were last updated on May 18, 2024.
Thu 6/62:36 pmMDW - SXM
2 stops25h 39mFrontier
Mon 6/106:25 pmSXM - MDW
2 stops44h 07mFrontier
Deal found 5/18$352
Thu 6/62:36 pmMDW - SXM
2 stops25h 39mFrontier
Mon 6/106:25 pmSXM - MDW
2 stops27h 55mFrontier
Deal found 5/17$397
Tue 6/256:00 amMDW - SXM
1 stop6h 55mDelta
Tue 7/23:20 pmSXM - MDW
2 stops18h 29mDelta
Deal found 5/16$824
Tue 6/256:00 amMDW - SXM
1 stop6h 55mDelta
Tue 7/23:20 pmSXM - MDW
1 stop21h 35mDelta
Deal found 5/16$893
Tue 6/46:00 amMDW - SXM
1 stop6h 40mDelta
Wed 6/53:10 pmSXM - MDW
1 stop17h 45mDelta
Deal found 5/17$905
Tue 6/46:00 amMDW - SXM
1 stop6h 40mDelta
Sat 6/153:20 pmSXM - MDW
2 stops18h 28mDelta
Deal found 5/17$984
Mon 5/206:00 amMDW - SXM
1 stop6h 40mDelta
Wed 5/223:10 pmSXM - MDW
1 stop17h 45mDelta
Deal found 5/16$1,005
Mon 5/206:00 amMDW - SXM
1 stop6h 40mDelta
Wed 5/223:10 pmSXM - MDW
2 stops18h 56mDelta
Deal found 5/16$1,009
Sat 6/86:00 amMDW - SXM
1 stop6h 55mDelta
Sat 6/153:20 pmSXM - MDW
2 stops18h 28mDelta
Deal found 5/18$1,137

Midway to St. Maarten 2024 flight deals

Discover exclusive flight deals for travel between Midway and St. Maarten in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,634,509 searches. Data last updated May 18, 2024.
Thu 6/62:36 pmMDW - SXM
2 stops25h 39mFrontier
Mon 6/106:25 pmSXM - MDW
2 stops44h 07mFrontier
Deal found 5/18$352
Thu 6/62:36 pmMDW - SXM
2 stops25h 39mFrontier
Mon 6/106:25 pmSXM - MDW
2 stops27h 55mFrontier
Deal found 5/17$397
Tue 7/236:55 pmMDW - SXM
1 stop17h 50mDelta
Sat 8/173:19 pmSXM - MDW
2 stops18h 25mDelta
Deal found 5/18$584
Fri 9/276:00 amMDW - SXM
1 stop6h 49mDelta
Mon 9/303:19 pmSXM - MDW
2 stops18h 26mDelta
Deal found 5/18$609
Fri 9/276:00 amMDW - SXM
1 stop6h 49mDelta
Mon 9/303:19 pmSXM - MDW
1 stop18h 58mDelta
Deal found 5/18$610
Tue 7/236:55 pmMDW - SXM
1 stop17h 50mDelta
Sat 8/173:19 pmSXM - MDW
1 stop21h 34mDelta
Deal found 5/18$810
Tue 6/256:00 amMDW - SXM
1 stop6h 55mDelta
Tue 7/23:20 pmSXM - MDW
2 stops18h 29mDelta
Deal found 5/16$824
Tue 6/256:00 amMDW - SXM
1 stop6h 55mDelta
Tue 7/23:20 pmSXM - MDW
1 stop21h 35mDelta
Deal found 5/16$893
Tue 10/155:59 pmMDW - SXM
2 stops18h 50mDelta
Sat 10/193:19 pmSXM - MDW
2 stops18h 26mDelta
Deal found 5/18$894

Midway to St. Maarten flights leaving soon

Find last-minute flight options from Midway to St. Maarten for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,634,509 searches. Data last updated May 18, 2024.
Fri 5/248:34 amMDW - SXM
3 stops28h 10mMultiple Airlines
Mon 5/2710:10 amSXM - MDW
3 stops24h 37mMultiple Airlines
Deal found 5/17$1,139
Fri 5/245:47 pmMDW - SXM
2 stops18h 03mDelta
Tue 5/283:10 pmSXM - MDW
2 stops18h 56mDelta
Deal found 5/17$1,152
Fri 5/246:00 amMDW - SXM
1 stop6h 40mDelta
Tue 5/283:10 pmSXM - MDW
2 stops18h 56mDelta
Deal found 5/17$1,282
Fri 5/245:47 pmMDW - SXM
2 stops18h 03mDelta
Tue 5/283:10 pmSXM - MDW
1 stop7h 51mDelta
Deal found 5/17$1,435
Fri 5/246:00 amMDW - SXM
1 stop6h 40mDelta
Tue 5/283:10 pmSXM - MDW
1 stop7h 51mDelta
Deal found 5/17$1,561
Fri 5/246:00 amMDW - SXM
1 stop6h 40mDelta
Tue 5/283:10 pmSXM - MDW
1 stop7h 51mDelta
Deal found 5/17$1,760
Sat 5/256:00 amMDW - SXM
1 stop6h 40mDelta
Sat 6/12:20 pmSXM - MDW
1 stop8h 41mDelta
Deal found 5/16$2,271
Sat 5/256:00 amMDW - SXM
1 stop6h 40mDelta
Sat 6/12:20 pmSXM - MDW
2 stops19h 46mDelta
Deal found 5/16$2,275

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 2,634,509 searches. Data last updated May 18, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$397 - $2,917

Route

Depart

Return

Price

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Thu 6/6

2 stops25h 39m

Simpson Bay Princess Juliana

Mon 6/10

2 stops27h 55m

$397

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Tue 7/23

1 stop17h 50m

Simpson Bay Princess Juliana

Sat 8/17

2 stops18h 25m

$584

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Tue 7/23

1 stop17h 50m

Simpson Bay Princess Juliana

Sat 8/17

1 stop21h 34m

$810

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Tue 6/25

1 stop6h 55m

Simpson Bay Princess Juliana

Tue 7/2

2 stops18h 29m

$824

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Tue 6/25

1 stop6h 55m

Simpson Bay Princess Juliana

Tue 7/2

1 stop21h 35m

$893

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Mon 7/22

1 stop17h 50m

Simpson Bay Princess Juliana

Sat 7/27

1 stop19h 16m

$895

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Wed 11/6

1 stop18h 34m

Simpson Bay Princess Juliana

Wed 11/13

2 stops18h 31m

$897

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Wed 11/6

1 stop18h 34m

Simpson Bay Princess Juliana

Wed 11/13

1 stop19h 03m

$898

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Thu 11/7

2 stops21h 22m

Simpson Bay Princess Juliana

Tue 11/12

2 stops24h 51m

$2,917

Flights are sorted by cheapest first

Deals found on 5/17

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 May 18, 2024.
Delta
8.0
Very good
10,647 reviews
Check prices

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Overall

8.0

Crew

8.6

Food

7.4

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.0
Very good
10,647 reviews
Delta
8.0
Very good
10,647 reviews
Check prices

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Overall

8.0

Crew

8.6

Food

7.4

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

WestJet
7.5
Good
2,899 reviews
Delta
8.0
Very good
10,647 reviews
Check prices

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Overall

8.0

Crew

8.6

Food

7.4

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Frontier
6.3
Okay
4,056 reviews
Delta
8.0
Very good
10,647 reviews
Check prices

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Overall

8.0

Crew

8.6

Food

7.4

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

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 flights from Chicago Midway Airport to St. Maarten for under $400 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to St. Maarten for under $400. The cheapest flight booked recently is on Frontier for just $397, but on average you can expect to pay $898.

  • Are there last-minute flights available from Chicago Midway Airport to St. Maarten for under $1,200?

    There are currently 8+ open flights from Chicago Midway Airport to St. Maarten within the next 7 days for less than $1,200.

  • What does MDW to SXM mean?

    Chicago Midway Airport is MDW and Simpson Bay Princess Juliana Airport is SXM. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service.

  • Can I find deals for flights from Midway to St. Maarten that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to St. Maarten flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to St. Maarten with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to St. Maarten flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Midway to St. Maarten that allow pets onboard?

    Many airlines flying from Midway to St. Maarten offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to St. Maarten?

    Yes, you can often find last-minute deals on Midway to St. Maarten flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to St. Maarten flight deals updated?

    The Chicago Midway Airport to St. Maarten flight deals you see on this page were last updated on 5/18.

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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Top airline flying from Midway to St. Maarten

Discover the top airline that operate flights from Midway to St. Maarten. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,634,509 searches. Data last updated May 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$473Average$946FlexibilityNo cancel feeOn-timeN/A
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Search flights from Midway to St. Maarten by cabin class

Find flights from Midway to St. Maarten, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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How does Cheapflights help users find flights from Midway to St. Maarten?

When you search for this flight from Midway to St. Maarten, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Midway to St. Maarten?

Cheapflights helps you find that perfect flight to St. Maarten from Midway by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Midway to St. Maarten with no change fees?

Need flexible booking options for your flight to St. Maarten from Midway? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Midway to St. Maarten become cheaper?

Not ready to book yet? You can track prices for flights from Midway to St. Maarten on Cheapflights with our Price Alert feature and get notified when better prices are available.

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