$208 Find Cheap Flights from Chicago Midway Airport to St. Maarten - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to St. Maarten departing on 11/18. 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.
1 adult
1 adult, Economy, 0 bags

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Book Cheap Midway to St. Maarten Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to St. Maarten that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

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

Thu, Sep 10 - Thu, Sep 17
Southwest Logo
5:00 am - 2:05 pm
MDW
-
SXM
8h 05m
1 stop
Southwest Logo
3:05 pm - 10:40 pm
SXM
-
MDW
8h 35m
1 stop
$385Southwest
Mon, Jul 20 - Wed, Jul 29
Southwest Logo
5:10 am - 1:25 pm
MDW
-
SXM
7h 15m
1 stop
Southwest Logo
3:00 pm - 10:05 pm
SXM
-
MDW
8h 05m
1 stop
$425Southwest
Mon, Jul 20 - Wed, Jul 29
Southwest Logo
5:10 am - 1:25 pm
MDW
-
SXM
7h 15m
1 stop
Southwest Logo
3:00 pm - 7:10 am
SXM
-
MDW
17h 10m
2 stops
$430Southwest
Thu, Sep 10 - Thu, Sep 17
Southwest Logo
4:25 pm - 2:05 pm
MDW
-
SXM
20h 40m
2 stops
Southwest Logo
3:05 pm - 10:40 pm
SXM
-
MDW
8h 35m
1 stop
$453Southwest
Mon, Jul 20 - Wed, Jul 29
Southwest Logo
8:50 pm - 2:00 pm
MDW
-
SXM
16h 10m
2 stops
Southwest Logo
3:00 pm - 7:10 am
SXM
-
MDW
17h 10m
2 stops
$457Southwest
Sat, Oct 3 - Sat, Oct 17
Southwest Logo
5:00 am - 1:45 pm
MDW
-
SXM
7h 45m
1 stop
Southwest Logo
2:45 pm - 7:25 am
SXM
-
MDW
17h 40m
2 stops
$485Southwest
Fri, Aug 14 - Fri, Aug 21
Southwest Logo
5:00 am - 2:05 pm
MDW
-
SXM
8h 05m
1 stop
Southwest Logo
3:05 pm - 10:40 pm
SXM
-
MDW
8h 35m
1 stop
$510Southwest
Thu, Dec 3 - Tue, Dec 8
Southwest Logo
8:50 pm - 2:20 pm
MDW
-
SXM
15h 30m
2 stops
Southwest Logo
3:20 pm - 5:40 am
SXM
-
MDW
16h 20m
2 stops
$511Southwest
Thu, Dec 3 - Tue, Dec 8
Southwest Logo
8:50 pm - 2:20 pm
MDW
-
SXM
15h 30m
2 stops
Southwest Logo
3:20 pm - 5:40 am
SXM
-
MDW
16h 20m
2 stops
$516Southwest
Mon, Jul 20 - Thu, Jul 23
Southwest Logo
5:10 am - 1:25 pm
MDW
-
SXM
7h 15m
1 stop
Southwest Logo
2:25 pm - 12:45 am
SXM
-
MDW
11h 20m
1 stop
$533Southwest
Booking Insights

KAYAK's insights & trends for Midway to St. Maarten flights

Get data-powered insights and trends into flights from Midway to St. Maarten to help you find the cheapest flights, the best time to fly and much more.

How long does a flight from Chicago Midway Airport to St. Maarten take?

The duration of a flight to St. Maarten depends on your arrival airport. The shortest route to St. Maarten from Chicago Midway Airport is to Simpson Bay, which takes 6h 49m.

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Good to know

Cheapest flight$208
Flight from Chicago Midway Airport to Simpson Bay

FAQs - booking St. Maarten flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to St. Maarten?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to St. Maarten.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to St. Maarten?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to St. Maarten is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to St. Maarten?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago Midway Airport to St. Maarten with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to St. Maarten?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport to St. Maarten up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight from Midway to St. Maarten

Information on your arrival and departure airports

Chicago Midway Airport (MDW)