$199 Find Cheap Flights from Chicago Midway Airport to Saint Martin Island

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 Saint Martin Island departing on 4/20. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Saint Martin Island

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Saint Martin Island, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Saint Martin Island, as well as popular online travel agencies
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Flight Deals

Book Cheap Midway to Saint Martin Island 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 Saint Martin Island 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 Saint Martin Island

Wed, Apr 22 - Thu, Apr 30
Southwest Logo
6:00 am - 1:30 pm
MDW
-
SXM
6h 30m
1 stop
Southwest Logo
2:25 pm - 12:05 am
SXM
-
MDW
10h 40m
1 stop
$521Southwest
Tue, Apr 28 - Tue, May 5
Southwest Logo
8:50 pm - 1:30 pm
MDW
-
SXM
15h 40m
2 stops
Southwest Logo
2:25 pm - 7:35 am
SXM
-
MDW
18h 10m
2 stops
$526Southwest
Wed, Apr 22 - Thu, Apr 30
Southwest Logo
6:00 am - 1:30 pm
MDW
-
SXM
6h 30m
1 stop
Southwest Logo
2:25 pm - 7:10 am
SXM
-
MDW
17h 45m
2 stops
$544Southwest
Mon, Apr 13 - Thu, Apr 23
Southwest Logo
5:35 am - 1:30 pm
MDW
-
SXM
6h 55m
1 stop
Southwest Logo
2:25 pm - 12:45 pm
SXM
-
MDW
23h 20m
2 stops
$590Southwest
Mon, Apr 27 - Mon, May 4
Southwest Logo
5:35 am - 1:30 pm
MDW
-
SXM
6h 55m
1 stop
Southwest Logo
2:25 pm - 7:35 am
SXM
-
MDW
18h 10m
2 stops
$598Southwest
Mon, Apr 13 - Thu, Apr 23
Southwest Logo
5:35 am - 1:30 pm
MDW
-
SXM
6h 55m
1 stop
Southwest Logo
2:25 pm - 12:05 am
SXM
-
MDW
10h 40m
1 stop
$603Southwest
Mon, Apr 13 - Thu, Apr 23
Southwest Logo
6:25 pm - 1:30 pm
MDW
-
SXM
18h 05m
2 stops
Southwest Logo
2:25 pm - 7:10 am
SXM
-
MDW
17h 45m
2 stops
$608Southwest
Thu, Apr 9 - Thu, Apr 16
Southwest Logo
5:35 am - 1:30 pm
MDW
-
SXM
6h 55m
1 stop
Southwest Logo
2:25 pm - 12:05 am
SXM
-
MDW
10h 40m
1 stop
$611Southwest
Wed, Apr 15 - Mon, Apr 20
Southwest Logo
8:50 pm - 1:30 pm
MDW
-
SXM
15h 40m
2 stops
Southwest Logo
2:25 pm - 12:05 am
SXM
-
MDW
10h 40m
1 stop
$616Southwest
Wed, Apr 8 - Wed, Apr 15
Southwest Logo
6:00 am - 1:30 pm
MDW
-
SXM
6h 30m
1 stop
Southwest Logo
2:25 pm - 7:10 am
SXM
-
MDW
17h 45m
2 stops
$623Southwest
Booking Insights

KAYAK's insights & trends for Midway to Saint Martin Island flights

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

Can I save money by flying with a layover from Chicago Midway Airport to Saint Martin Island?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $381, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$199
Flight from Chicago Midway Airport to Simpson Bay

FAQs - booking Saint Martin Island flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Saint Martin Island?

    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 Saint Martin Island.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Saint Martin Island 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 Saint Martin Island?

    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 Saint Martin Island 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 Saint Martin Island?

    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 Saint Martin Island up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Saint Martin Island

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Saint Martin Island. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Saint Martin Island? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8295 reviews
8.5Crew
7.2Food
8.1Boarding
7.9Comfort
7.8Entertainment
Airline reviews

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

10.0 ExcellentAnonymous, Mar 2026
ATL - DTW
Read more Delta reviews

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

No WiFi. Arrival was early but gate was occupied and had to sit on jet 30 min to deplane.

No WiFi on flight. Arrival was early but gate was occupied and had to sit on jet for nearly 30 min to deplane.

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Everything you need to know for your flight to Saint Martin Island

Information on your arrival and departure airports

Chicago Midway Airport (MDW)