Southwest® flights from Chicago (Midway) to St. Maarten

Promo Code
St. Marteen

Visit St. Maarten


Reserve your seat for flights to St. Maarten and soak up turquoise waters, vibrant culture, and island adventure.

Flights available to book today. Service starts April 7, 2026.

Find flights

Low fares from Chicago (Midway) to St. Maarten

$

Low fares from Chicago (Midway) to St. Maarten

$

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Chicago (Midway) to St. Maarten

Flight Details

Departing from:
Chicago Midway International Airport
Arriving at:
Princess Juliana International Airport
Distance:
2189 miles

Route Information

10† Weekly flights

† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

Questions we hear the most

There are 10 weekly flights from Chicago (Midway) to St. Maarten on Southwest Airlines.
To find the lowest fares by day and time to fly Chicago (Midway) to St. Maarten with Southwest, check out our Low Fare Calendar.
You can rent a car at Princess Juliana International Airport book yours with your flight.
Yes! Flights from Chicago (Midway) to St. Maarten—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.

Explore Flights from Other Popular Origins

Popular Flights from Chicago (Midway)