$240 Find Cheap Flights from Chicago Midway Airport to St. Maarten - Compare and Save

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Book Cheap Midway to St. Maarten Plane Tickets

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to St. Maarten

Sun, Jan 24 - Thu, Jan 28
Southwest Logo
5:25 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 50m1 stop Orlando
Southwest Logo
3:15 pm - 10:55 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 40m1 stop Orlando
$577Southwest
Sun, Jan 24 - Thu, Jan 28
Southwest Logo
5:25 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 50m1 stop Orlando
Southwest Logo
3:15 pm - 10:15 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
21h 00m2 stops Orlando Denver Intl
$581Southwest
Sun, Jan 17 - Fri, Jan 22
Delta Logo
6:00 am - 2:57 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 57m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:50 pm - 11:55 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
12h 05m1 stop Atlanta Hartsfield-Jackson
$593Delta
Mon, Feb 1 - Fri, Feb 5
Southwest Logo
5:25 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 50m1 stop Orlando
Southwest Logo
3:15 pm - 11:25 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
10h 10m1 stop Orlando
$595Southwest
Tue, Jan 26 - Tue, Feb 2
Delta Logo
1:41 pm - 12:20 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
20h 39m2 stops Detroit Metropolitan Wayne County New York LaGuardia
Delta Logo
1:50 pm - 11:55 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
12h 05m1 stop Atlanta Hartsfield-Jackson
$597Delta
Sun, Jan 31 - Thu, Feb 4
Southwest Logo
9:35 pm - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
14h 40m2 stops Denver Intl Orlando
Southwest Logo
4:40 pm - 8:55 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
18h 15m2 stops Baltimore/Washington Orlando
$599Southwest
Sun, Jan 24 - Thu, Jan 28
Southwest Logo
5:25 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 50m1 stop Orlando
Southwest Logo
3:15 pm - 10:55 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 40m1 stop Orlando
$613Southwest
Sun, Jan 24 - Thu, Jan 28
Southwest Logo
3:40 pm - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
20h 35m2 stops Phoenix Sky Harbor Intl Orlando
Southwest Logo
3:15 pm - 10:55 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 40m1 stop Orlando
$617Southwest
Wed, Dec 2 - Wed, Dec 9
Southwest Logo
4:10 pm - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
20h 05m2 stops Las Vegas Harry Reid Intl Orlando
Southwest Logo
3:15 pm - 12:05 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
22h 50m2 stops Orlando Las Vegas Harry Reid Intl
$627Southwest
Wed, Feb 3 - Tue, Feb 9
Delta Logo
6:00 am - 2:57 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 57m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:23 pm - 9:16 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
18h 53m2 stops New York John F Kennedy Intl Detroit Metropolitan Wayne County
$629Delta
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to St. Maarten flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Chicago Midway Airport to St. Maarten right now?

The cheapest fare from Chicago Midway Airport to St. Maarten in the last week was $577 round-trip, to Simpson Bay Princess Juliana (SXM).

Which airport in St. Maarten is the cheapest to fly to from Chicago Midway Airport?

All flights from Chicago Midway Airport to St. Maarten arrive at Simpson Bay Princess Juliana (SXM). On average, round-trip fares are around $670.

What’s the cheapest day to fly from Chicago Midway Airport to St. Maarten?

Sunday tends to be the cheapest day to fly from Chicago Midway Airport to St. Maarten, while Monday is the most expensive. Fares run about 54% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Chicago Midway Airport to St. Maarten?

Data from the past 12 months shows it's cheapest to fly to St. Maarten during the night with average prices of $531. The morning is the most expensive time to fly, with average prices of $684.

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Key details for Chicago Midway Airport to St. Maarten flights

Low season

May

Cheapest flight

$240
Beat the crowds with an average 72% drop in travelers.
The most popular month to fly with an average 38% increase in travelers.
One-way flight from Chicago Midway Airport to Simpson Bay

Your Chicago Midway Airport to St. Maarten flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago Midway Airport to St. Maarten?

    Fares from Chicago Midway Airport to St. Maarten are around their usual level right now. A round-trip under $557 is considered a good deal, so it's worth keeping an eye out, or setting a Price Alert to catch price changes.

  • How much should I budget for a flight from Chicago Midway Airport to St. Maarten?

    Over the past 12 months, round-trip fares from Chicago Midway Airport to St. Maarten have ranged from $557 to $750.

  • What are the main airports serving St. Maarten?

    Flights to St. Maarten all arrive at Simpson Bay Princess Juliana (SXM).

  • What airlines fly nonstop from Chicago Midway Airport to St. Maarten?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Chicago Midway Airport to St. Maarten. One-stop options include Southwest and Delta.

  • Which cabin classes are available on flights from Chicago Midway Airport to St. Maarten?

    On flights from Chicago Midway Airport to St. Maarten you can only book Economy Class.

Your guide to booking Chicago Midway Airport to St. Maarten flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your travel dates are flexible, book your trip for May when flights are typically cheapest and avoid March when prices are at their highest.
  • Flying on Sunday is usually the cheapest. Flights on Monday cost about 54% more on average, so being flexible with your travel dates could help you save.
  • Start your trip in Simpson Bay, which is the most popular destination in St. Maarten. From there, it's easy to continue on to other popular destinations such as Lowlands, Philipsburg and Cole Bay.

More options for your flight from Midway to St. Maarten

Complete your trip to St. Maarten with a hotel stay or car rental

Car rentals in St. Maarten
Hotels in St. Maarten
Vacations in St. Maarten