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$388+ Cheap flights from St. Maarten to Midway (MDW)

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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Dec 25 — Jan 11
Wed 12/25
Wed 1/1
1 adult, Economy
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Cheap flight deals from St. Maarten to Midway

Discover tips and strategies to find the most affordable flight options for your journey from St. Maarten (SX0) to Midway (MDW). 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 December 20, 2024.

Round-trip from

$776
(Mytrip)

One-way from

$388
(Delta)
From St. Maarten to Chicago Midway
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One-way flight from St. Maarten to Chicago Midway
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Find flight deals from St. Maarten to Midway

Best flights from St. Maarten to Midway
Discover carefully curated flight deals from St. Maarten to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 20, 2024.

This Mytrip deal was found by Cheapflights users on 12/17. 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.
Sun 1/124:55 pmSXM - MDW
2 stops21h 15mMultiple Airlines
Sun 1/191:05 pmMDW - SXM
2 stops20h 50mMultiple Airlines
Deal found 12/17$776
This Delta deal was found by Cheapflights users on 12/17. 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 1/121:40 pmSXM - MDW
1 stop10h 40mDelta
Sun 1/196:00 amMDW - SXM
1 stop7h 16mDelta
Deal found 12/17$1,176

Find flights from St. Maarten to Midway within your budget

Customize your flight search to find flights from St. Maarten to Midway 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 December 20, 2024.

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Depart

Return

Price

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 1/12

4:55 pm-12:10 pm

2 stops21h 15m

Chicago Midway

Sun 1/19

1:05 pm-11:55 am

2 stops20h 50m

$776

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 1/12

1:40 pm-10:20 pm

1 stop10h 40m

Chicago Midway

Sun 1/19

6:00 am-3:16 pm

1 stop7h 16m

$1,176

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 4/3

1:40 pm-10:27 pm

1 stop9h 47m

$388

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 4/3

3:10 pm-2:15 pm

2 stops24h 05m

$465

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 4/3

12:05 pm-2:15 pm

3 stops27h 10m

$500

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 1/3

6:29 pm-3:13 pm

2 stops22h 44m

$804

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

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

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

Travel insights for flights from St. Maarten to Midway

Get recent, data-driven insights about flights from St. Maarten to Midway including ideal travel times, pricing trends, and more.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated December 20, 2024.
Delta
8.0
Very good
8,600 reviews

Boarding

8.2

Crew

8.6

Food

7.3

Comfort

8.0

Entertainment

7.9

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,600 reviews
Delta
8.0
Very good
8,600 reviews

Boarding

8.2

Crew

8.6

Food

7.3

Comfort

8.0

Entertainment

7.9

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

WestJet
7.3
Good
2,816 reviews
Delta
8.0
Very good
8,600 reviews

Boarding

8.2

Crew

8.6

Food

7.3

Comfort

8.0

Entertainment

7.9

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Frontier
6.1
Okay
3,475 reviews
Delta
8.0
Very good
8,600 reviews

Boarding

8.2

Crew

8.6

Food

7.3

Comfort

8.0

Entertainment

7.9

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

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

  • What are the cheapest airlines to fly from St. Maarten to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $388. WestJet flights start at $465 while deals on Frontier start at $804 one-way.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from St. Maarten to Chicago Midway Airport (average of $160). Flying from St. Maarten to Chicago Midway Airport in November is currently the most expensive (average of $249). 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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