$328 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

Sat, Mar 28 - Sat, Apr 4
Multiple Airlines Logo
12:45 pm - 2:17 pm
MDW
-
SXM
24h 32m
1 stop
Multiple Airlines Logo
2:14 pm - 10:21 pm
SXM
-
MDW
33h 07m
2 stops
$546Multiple Airlines
Tue, Apr 21 - Fri, Apr 24
Southwest Logo
8:55 pm - 1:40 pm
MDW
-
SXM
15h 45m
2 stops
Southwest Logo
2:35 pm - 7:55 am
SXM
-
MDW
18h 20m
2 stops
$576Southwest
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
$601Delta
Sat, Mar 28 - Sat, Apr 4
Multiple Airlines Logo
12:45 pm - 1:35 pm
MDW
-
SXM
23h 50m
2 stops
Multiple Airlines Logo
2:40 pm - 3:20 pm
SXM
-
MDW
25h 40m
2 stops
$609Multiple Airlines
Sat, Mar 28 - Sun, Apr 5
Multiple Airlines Logo
9:16 pm - 1:08 pm
MDW
-
SXM
38h 52m
2 stops
Multiple Airlines Logo
3:20 pm - 10:05 am
SXM
-
MDW
19h 45m
1 stop
$613Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m
1 stop
Delta Logo
1:38 pm - 10:33 pm
SXM
-
MDW
10h 55m
1 stop
$615Delta
Sun, Jun 14 - Thu, Jun 18
Southwest Logo
5:05 am - 1:15 pm
MDW
-
SXM
7h 10m
1 stop
Southwest Logo
3:00 pm - 12:40 am
SXM
-
MDW
10h 40m
1 stop
$625Southwest
Thu, May 21 - Wed, May 27
Southwest Logo
9:15 pm - 1:40 pm
MDW
-
SXM
15h 25m
2 stops
Southwest Logo
2:35 pm - 7:10 am
SXM
-
MDW
17h 35m
2 stops
$630Southwest
Thu, Mar 12 - 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
$631Delta
Sun, Jun 14 - Thu, Jun 18
Southwest Logo
5:05 am - 1:15 pm
MDW
-
SXM
7h 10m
1 stop
Southwest Logo
3:00 pm - 9:20 am
SXM
-
MDW
19h 20m
2 stops
$650Southwest
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 $383, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight$223
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 8111 reviews
8.1Boarding
7.2Food
7.9Comfort
7.8Entertainment
8.5Crew
Airline reviews

The flight was comfortable and uneventful, which is what I desire

8.0 ExcellentLarry, Jan 2026
JFK - SJD
Read more Delta reviews

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

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

Information on your arrival and departure airports