$182 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 5/11. 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, Apr 4 - Sat, Apr 11
Frontier Logo
6:40 am - 3:15 pm
MDW
-
SXM
7h 35m
1 stop
Frontier Logo
4:20 pm - 8:07 pm
SXM
-
MDW
28h 47m
1 stop
$388Frontier
Sat, Apr 4 - Sat, Apr 11
Frontier Logo
6:40 am - 3:15 pm
MDW
-
SXM
7h 35m
1 stop
Frontier Logo
4:20 pm - 8:07 pm
SXM
-
MDW
28h 47m
1 stop
$393Frontier
Sat, Apr 4 - Sat, Apr 11
Frontier Logo
6:40 am - 3:15 pm
MDW
-
SXM
7h 35m
1 stop
Frontier Logo
4:20 pm - 8:07 pm
SXM
-
MDW
28h 47m
1 stop
$445Frontier
Sat, Apr 4 - Sat, Apr 11
Frontier Logo
6:40 am - 3:15 pm
MDW
-
SXM
7h 35m
1 stop
Frontier Logo
4:20 pm - 8:07 pm
SXM
-
MDW
28h 47m
1 stop
$495Frontier
Sun, May 17 - Thu, May 21
Southwest Logo
5:05 am - 2:25 pm
MDW
-
SXM
8h 20m
1 stop
Southwest Logo
2:25 pm - 12:05 am
SXM
-
MDW
10h 40m
1 stop
$625Southwest
Sun, May 17 - Thu, May 21
Southwest Logo
8:55 pm - 1:30 pm
MDW
-
SXM
15h 35m
2 stops
Southwest Logo
2:25 pm - 12:05 am
SXM
-
MDW
10h 40m
1 stop
$630Southwest
Sat, Apr 4 - Sat, Apr 11
Frontier Logo
6:40 am - 3:15 pm
MDW
-
SXM
7h 35m
1 stop
Frontier Logo
6:51 pm - 10:21 pm
SXM
-
MDW
28h 30m
2 stops
$631Frontier
Fri, May 29 - Tue, Jun 2
Southwest Logo
12:45 pm - 12:25 pm
MDW
-
SXM
22h 40m
2 stops
Southwest Logo
2:25 pm - 7:35 am
SXM
-
MDW
18h 10m
2 stops
$650Southwest
Sat, Apr 18 - Sat, May 2
Southwest Logo
5:15 am - 1:40 pm
MDW
-
SXM
7h 25m
1 stop
Southwest Logo
1:20 pm - 10:35 pm
SXM
-
MDW
10h 15m
1 stop
$665Southwest
Thu, Jun 11 - Mon, Jun 15
Southwest Logo
8:50 pm - 1:25 pm
MDW
-
SXM
15h 35m
2 stops
Southwest Logo
2:25 pm - 8:40 am
SXM
-
MDW
19h 15m
2 stops
$670Southwest
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 $384, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight$182
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 8340 reviews
8.1Boarding
7.8Entertainment
8.5Crew
7.9Comfort
7.2Food
Airline reviews

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

2.0 MediocreAliya, Mar 2026
JFK - ATL
Read more Delta reviews

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

It was fine. 55 minute flight. No snacks or beverage service offered. Boarding went smoothly and my walker was waiting for me on the jet way.

Smaller plane for a longer flight than my first one. Doesn’t make sense.

The cabin temperature was nice and cool. The wifi was not working.

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

Information on your arrival and departure airports