$138 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 4/4. 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

Di, Apr 7 - Di, Apr 14
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
$506Southwest
Mi, Apr 8 - Mi, Apr 15
Southwest Logo
8:55 pm - 1:30 pm
MDW
-
SXM
15h 35m
2 stops
Southwest Logo
2:25 pm - 7:10 am
SXM
-
MDW
17h 45m
2 stops
$526Southwest
Di, Mai 5 - Sa, Mai 9
Southwest Logo
6:00 am - 1:30 pm
MDW
-
SXM
6h 30m
1 stop
Southwest Logo
1:20 pm - 10:35 pm
SXM
-
MDW
10h 15m
1 stop
$573Southwest
Di, Mai 5 - Sa, Mai 9
Southwest Logo
8:50 pm - 1:30 pm
MDW
-
SXM
15h 40m
2 stops
Southwest Logo
1:20 pm - 10:35 pm
SXM
-
MDW
10h 15m
1 stop
$578Southwest
Mo, Apr 13 - Do, 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
Mo, Apr 13 - Do, 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
Mo, Apr 13 - Do, 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
Do, Apr 9 - Do, 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
Mi, Apr 15 - Mo, 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
Mi, Apr 8 - Mi, 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 $380, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight$138
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 8285 reviews
7.8Entertainment
7.9Comfort
8.5Crew
8.1Boarding
7.2Food
Airline reviews

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.

4.0 OkayJeffrey, Mar 2026
CMH - DTW
Read more Delta reviews

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.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

Delayed. Hot. Passenger next to me was so large I couldn’t move.

Same experience as the flight from Norfolk to Atlanta where people are boarded in zones that don't make sense. People behind you on the plane will get on before you and they take the luggage space on your row.

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

Information on your arrival and departure airports