$131 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 5/5. 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

Sat, Mar 7 - Sat, Mar 14
Frontier Logo
6:00 am - 3:20 pm
MDW
-
SXM
7h 20m
1 stop
Frontier Logo
2:35 pm - 10:09 pm
SXM
-
MDW
8h 34m
1 stop
$343Frontier
Mon, May 4 - Sat, May 9
Southwest Logo
5:35 am - 1:40 pm
MDW
-
SXM
7h 05m
1 stop
Southwest Logo
1:20 pm - 10:15 pm
SXM
-
MDW
9h 55m
1 stop
$581Southwest
Tue, Apr 28 - Mon, May 4
Southwest Logo
6:00 am - 1:40 pm
MDW
-
SXM
6h 40m
1 stop
Southwest Logo
2:35 pm - 7:35 am
SXM
-
MDW
18h 00m
2 stops
$586Southwest
Wed, Mar 11 - Mon, Mar 16
Delta Logo
6:00 am - 1:54 pm
MDW
-
SXM
6h 54m
1 stop
Delta Logo
12:55 pm - 10:31 pm
SXM
-
MDW
10h 36m
1 stop
$610Delta
Fri, Mar 6 - Wed, Mar 11
Multiple Airlines Logo
9:51 pm - 2:15 pm
MDW
-
SXM
14h 24m
2 stops
Multiple Airlines Logo
3:20 pm - 10:05 am
SXM
-
MDW
19h 45m
1 stop
$614Multiple Airlines
Tue, Mar 17 - Tue, Mar 24
Delta Logo
6:00 am - 1:54 pm
MDW
-
SXM
6h 54m
1 stop
Delta Logo
12:55 pm - 10:31 pm
SXM
-
MDW
10h 36m
1 stop
$625Delta
Wed, May 20 - Wed, May 27
Southwest Logo
6:00 am - 1:40 pm
MDW
-
SXM
6h 40m
1 stop
Southwest Logo
2:35 pm - 7:10 am
SXM
-
MDW
17h 35m
2 stops
$630Southwest
Sat, Mar 28 - Wed, Apr 1
Multiple Airlines Logo
9:16 pm - 1:30 pm
MDW
-
SXM
15h 14m
2 stops
Multiple Airlines Logo
3:20 pm - 10:05 am
SXM
-
MDW
19h 45m
1 stop
$631Multiple Airlines
Fri, Mar 27 - Tue, Mar 31
Multiple Airlines Logo
11:00 am - 10:55 am
MDW
-
SXM
22h 55m
2 stops
Multiple Airlines Logo
3:20 pm - 10:05 am
SXM
-
MDW
19h 45m
1 stop
$639Multiple Airlines
Thu, May 14 - Sun, May 17
Southwest Logo
5:35 am - 1:40 pm
MDW
-
SXM
7h 05m
1 stop
Southwest Logo
3:20 pm - 11:40 pm
SXM
-
MDW
9h 20m
1 stop
$645Southwest
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 $374, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$131
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 8205 reviews
7.9Comfort
8.5Crew
7.2Food
8.1Boarding
7.8Entertainment
Airline reviews

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

10.0 ExcellentSoosnata, Feb 2026
LAX - HNL
Read more Delta reviews

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Excellent!!! Aeromexico is a great airline. What was not that good is the service provided by Kayak. It is never clear and not easy to manage.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)