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Cheap flights from Midway (MDW) to St. Maarten from $183

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 5/18. 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 13 — May 201
From?
To?
Mon 5/13
Mon 5/20
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 $743 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 Frontier flights from Midway to St. Maarten

Explore cheap flight options specifically provided by Frontier 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 2,752,338 searches. Data last updated May 8, 2024.
Take a look at some of the lowest-priced Frontier flights heading from Chicago to St. Maarten. Be sure to come back soon if the deals available don't appeal to you at this time.
Sat 5/189:08 pmMDW - SXM
1 stop16h 59mFrontier
Sat 6/14:27 pmSXM - MDW
1 stop15h 27mFrontier
Deal found 5/8$183
Fri 5/171:15 pmMDW - SXM
1 stop24h 49mFrontier
Sat 5/254:14 pmSXM - MDW
1 stop15h 40mFrontier
Deal found 5/7$189
Thu 6/68:51 pmMDW - SXM
2 stops19h 24mFrontier
Fri 6/146:25 pmSXM - MDW
2 stops15h 09mFrontier
Deal found 5/7$299
Sat 5/187:53 amMDW - SXM
2 stops30h 14mFrontier
Sat 6/14:27 pmSXM - MDW
1 stop15h 27mFrontier
Deal found 5/8$327
Thu 8/12:54 pmMDW - SXM
2 stops22h 37mFrontier
Mon 8/54:04 pmSXM - MDW
2 stops30h 06mFrontier
Deal found 5/8$384
Fri 6/77:30 amMDW - SXM
2 stops30h 40mFrontier
Fri 6/146:25 pmSXM - MDW
2 stops15h 09mFrontier
Deal found 5/8$792
Sat 7/610:08 amMDW - SXM
2 stops51h 23mFrontier
Sat 7/134:30 pmSXM - MDW
1 stop22h 29mFrontier
Deal found 5/7$928
Sat 7/610:08 amMDW - SXM
2 stops51h 23mFrontier
Sat 7/134:30 pmSXM - MDW
2 stops29h 19mFrontier
Deal found 5/7$989

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 2,752,338 searches. Data last updated May 8, 2024.
Take a gander at the lowest prices we've found on Delta flights from Chicago to St. Maarten. Make sure to examine the flight information before completing your reservation.
Tue 7/236:49 pmMDW - SXM
1 stop18h 00mDelta
Sat 8/173:19 pmSXM - MDW
2 stops18h 25mDelta
Deal found 5/7$584
Mon 8/126:00 amMDW - SXM
1 stop6h 49mDelta
Sun 8/183:19 pmSXM - MDW
1 stop21h 34mDelta
Deal found 5/7$585
Tue 9/105:59 pmMDW - SXM
2 stops18h 50mDelta
Sun 9/153:19 pmSXM - MDW
1 stop21h 39mDelta
Deal found 5/7$589
Tue 9/103:45 pmMDW - SXM
1 stop21h 04mDelta
Sun 9/153:19 pmSXM - MDW
1 stop21h 39mDelta
Deal found 5/7$590
Sat 6/86:00 amMDW - SXM
1 stop6h 55mDelta
Sat 6/153:38 pmSXM - MDW
2 stops21h 17mDelta
Deal found 5/7$609
Sat 8/176:00 amMDW - SXM
1 stop6h 49mDelta
Sat 8/243:19 pmSXM - MDW
1 stop21h 34mDelta
Deal found 5/7$610
Tue 10/11:10 pmMDW - SXM
2 stops23h 39mDelta
Fri 10/43:19 pmSXM - MDW
2 stops18h 26mDelta
Deal found 5/7$639
Tue 10/13:45 pmMDW - SXM
1 stop21h 04mDelta
Fri 10/43:19 pmSXM - MDW
2 stops18h 26mDelta
Deal found 5/7$644
Tue 10/110:11 amMDW - SXM
1 stop26h 38mDelta
Fri 10/43:19 pmSXM - MDW
1 stop18h 58mDelta
Deal found 5/7$645

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 2,752,338 searches. Prices were last updated on May 8, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to St. Maarten in 2024. Check back regularly for other flight deals.
Sat 5/189:08 pmMDW - SXM
1 stop16h 59mFrontier
Sat 6/14:27 pmSXM - MDW
1 stop15h 27mFrontier
Deal found 5/8$183
Fri 5/171:15 pmMDW - SXM
1 stop24h 49mFrontier
Sat 5/254:14 pmSXM - MDW
1 stop15h 40mFrontier
Deal found 5/7$189
Sat 6/110:08 amMDW - SXM
1 stop27h 56mFrontier
Sat 6/84:20 pmSXM - MDW
1 stop18h 11mFrontier
Deal found 5/8$268
Sat 6/17:53 amMDW - SXM
2 stops30h 11mFrontier
Sat 6/84:20 pmSXM - MDW
1 stop18h 11mFrontier
Deal found 5/8$272
Fri 6/281:11 pmMDW - SXM
1 stop24h 59mFrontier
Mon 7/16:25 pmSXM - MDW
2 stops29h 41mFrontier
Deal found 5/8$274
Thu 6/68:51 pmMDW - SXM
2 stops19h 24mFrontier
Fri 6/146:25 pmSXM - MDW
2 stops15h 09mFrontier
Deal found 5/7$299
Sat 5/187:53 amMDW - SXM
2 stops30h 14mFrontier
Sat 6/14:27 pmSXM - MDW
1 stop15h 27mFrontier
Deal found 5/8$327
Fri 6/287:30 amMDW - SXM
2 stops30h 40mFrontier
Mon 7/16:25 pmSXM - MDW
2 stops27h 55mFrontier
Deal found 5/8$379
Sat 6/17:53 amMDW - SXM
2 stops30h 11mFrontier
Sat 6/84:20 pmSXM - MDW
2 stops28h 36mFrontier
Deal found 5/8$383

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 2,752,338 searches. Data last updated May 8, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to St. Maarten in 2024. Check back regularly for other flight deals.
Sat 5/189:08 pmMDW - SXM
1 stop16h 59mFrontier
Sat 6/14:27 pmSXM - MDW
1 stop15h 27mFrontier
Deal found 5/8$183
Fri 5/171:15 pmMDW - SXM
1 stop24h 49mFrontier
Sat 5/254:14 pmSXM - MDW
1 stop15h 40mFrontier
Deal found 5/7$189
Sat 6/110:08 amMDW - SXM
1 stop27h 56mFrontier
Sat 6/84:20 pmSXM - MDW
1 stop18h 11mFrontier
Deal found 5/8$268
Sat 6/17:53 amMDW - SXM
2 stops30h 11mFrontier
Sat 6/84:20 pmSXM - MDW
1 stop18h 11mFrontier
Deal found 5/8$272
Fri 6/281:11 pmMDW - SXM
1 stop24h 59mFrontier
Mon 7/16:25 pmSXM - MDW
2 stops29h 41mFrontier
Deal found 5/8$274
Thu 6/68:51 pmMDW - SXM
2 stops19h 24mFrontier
Fri 6/146:25 pmSXM - MDW
2 stops15h 09mFrontier
Deal found 5/7$299
Sat 5/187:53 amMDW - SXM
2 stops30h 14mFrontier
Sat 6/14:27 pmSXM - MDW
1 stop15h 27mFrontier
Deal found 5/8$327
Fri 6/287:30 amMDW - SXM
2 stops30h 40mFrontier
Mon 7/16:25 pmSXM - MDW
2 stops27h 55mFrontier
Deal found 5/8$379
Sat 6/17:53 amMDW - SXM
2 stops30h 11mFrontier
Sat 6/84:20 pmSXM - MDW
2 stops28h 36mFrontier
Deal found 5/8$383

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 2,752,338 searches. Data last updated May 8, 2024.
Consider one of these great deals we found on last-minute flights from Chicago to St. Maarten. Users should be sure to double check the price, date, and time of their last-minute flight.
Sat 5/189:08 pmMDW - SXM
1 stop16h 59mFrontier
Sat 6/14:27 pmSXM - MDW
1 stop15h 27mFrontier
Deal found 5/8$183
Fri 5/171:15 pmMDW - SXM
1 stop24h 49mFrontier
Sat 5/254:14 pmSXM - MDW
1 stop15h 40mFrontier
Deal found 5/7$189
Sat 5/187:53 amMDW - SXM
2 stops30h 14mFrontier
Sat 6/14:27 pmSXM - MDW
1 stop15h 27mFrontier
Deal found 5/8$327
Fri 5/176:48 pmMDW - SXM
1 stop17h 52mDelta
Sat 5/253:25 pmSXM - MDW
2 stops19h 46mDelta
Deal found 5/7$919
Fri 5/175:47 pmMDW - SXM
2 stops18h 03mDelta
Sat 5/253:25 pmSXM - MDW
2 stops19h 46mDelta
Deal found 5/7$1,024
Tue 5/146:00 amMDW - SXM
1 stop6h 40mDelta
Sat 5/182:20 pmSXM - MDW
1 stop18h 35mDelta
Deal found 5/6$1,119
Tue 5/146:00 amMDW - SXM
1 stop6h 40mDelta
Sat 5/182:20 pmSXM - MDW
1 stop8h 41mDelta
Deal found 5/7$1,189

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 2,752,338 searches. Data last updated May 8, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$299 - $868

Route

Depart

Return

Price

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Thu 6/6

2 stops19h 24m

Simpson Bay Princess Juliana

Fri 6/14

2 stops15h 09m

$299

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Thu 8/1

2 stops22h 37m

Simpson Bay Princess Juliana

Mon 8/5

2 stops30h 06m

$384

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Tue 7/23

1 stop18h 00m

Simpson Bay Princess Juliana

Sat 8/17

2 stops18h 25m

$584

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Mon 8/12

1 stop6h 49m

Simpson Bay Princess Juliana

Sun 8/18

1 stop21h 34m

$585

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Tue 9/10

2 stops18h 50m

Simpson Bay Princess Juliana

Sun 9/15

1 stop21h 39m

$589

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Tue 9/10

1 stop21h 04m

Simpson Bay Princess Juliana

Sun 9/15

1 stop21h 39m

$590

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Sat 6/8

1 stop6h 55m

Simpson Bay Princess Juliana

Sat 6/15

2 stops21h 17m

$609

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Fri 6/7

2 stops30h 40m

Simpson Bay Princess Juliana

Fri 6/14

2 stops15h 09m

$792

Chicago MidwaySimpson Bay Princess Juliana

MDW - SXM

MDWSXM

Chicago Midway

Mon 6/17

3 stops37h 19m

Simpson Bay Princess Juliana

Sun 6/23

3 stops31h 08m

$868

Flights are sorted by cheapest first

Deals found on 5/7

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 8, 2024.
Get a feel of what it's like to fly with Frontier and Delta from Chicago to St. Maarten by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
10,789 reviews
Check prices

Comfort

7.9

Overall

8.1

Boarding

8.2

Crew

8.6

Food

7.4

Entertainment

8.0

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
8.1
Very good
10,789 reviews
Delta
8.1
Very good
10,789 reviews
Check prices

Comfort

7.9

Overall

8.1

Boarding

8.2

Crew

8.6

Food

7.4

Entertainment

8.0

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
4,088 reviews
Delta
8.1
Very good
10,789 reviews
Check prices

Comfort

7.9

Overall

8.1

Boarding

8.2

Crew

8.6

Food

7.4

Entertainment

8.0

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 $300 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to St. Maarten for under $300. The cheapest flight booked recently is on Frontier for just $299, but on average you can expect to pay $662.

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

    There are currently 7+ open flights from Chicago Midway Airport to St. Maarten within the next 7 days for less than $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 5/8.

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 2,752,338 searches. Data last updated May 8, 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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Fly with Cheapflights

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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.

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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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