$130 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 5/9. 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

Sa, Mai 16 - Mo, Mai 25
Multiple Airlines Logo
11:59 am - 1:30 pm
MDW
-
SXM
24h 31m
2 stops
Multiple Airlines Logo
3:20 pm - 9:45 am
SXM
-
MDW
19h 25m
1 stop
$473Multiple Airlines
Sa, Mai 16 - Do, Mai 21
Multiple Airlines Logo
11:59 am - 1:30 pm
MDW
-
SXM
24h 31m
2 stops
Multiple Airlines Logo
3:20 pm - 2:35 pm
SXM
-
MDW
24h 15m
1 stop
$495Multiple Airlines
Mi, Jul 15 - Mo, Jul 20
Multiple Airlines Logo
3:20 pm - 2:20 pm
MDW
-
SXM
22h 00m
1 stop
Multiple Airlines Logo
3:20 pm - 9:40 am
SXM
-
MDW
19h 20m
1 stop
$559Multiple Airlines
So, Mai 17 - Do, Mai 28
Multiple Airlines Logo
10:30 am - 2:20 pm
MDW
-
SXM
26h 50m
1 stop
Multiple Airlines Logo
3:20 pm - 2:35 pm
SXM
-
MDW
24h 15m
1 stop
$564Multiple Airlines
So, Mai 17 - Do, Mai 28
Multiple Airlines Logo
3:20 pm - 2:20 pm
MDW
-
SXM
22h 00m
1 stop
Multiple Airlines Logo
2:35 pm - 11:09 am
SXM
-
MDW
21h 34m
2 stops
$566Multiple Airlines
Mi, Jul 15 - So, Jul 19
Multiple Airlines Logo
3:20 pm - 2:20 pm
MDW
-
SXM
22h 00m
1 stop
Multiple Airlines Logo
3:20 pm - 9:40 am
SXM
-
MDW
19h 20m
1 stop
$574Multiple Airlines
Mo, Mai 11 - Mo, Mai 18
Southwest Logo
5:35 am - 1:30 pm
MDW
-
SXM
6h 55m
1 stop
Southwest Logo
2:25 pm - 12:15 am
SXM
-
MDW
10h 50m
1 stop
$590Southwest
Mo, Mai 11 - Mo, Mai 18
Southwest Logo
7:40 pm - 1:30 pm
MDW
-
SXM
16h 50m
2 stops
Southwest Logo
2:25 pm - 7:35 am
SXM
-
MDW
18h 10m
2 stops
$595Southwest
Di, Mai 12 - Di, Mai 19
Southwest Logo
6:00 am - 1:30 pm
MDW
-
SXM
6h 30m
1 stop
Southwest Logo
2:25 pm - 7:35 am
SXM
-
MDW
18h 10m
2 stops
$620Southwest
So, Jul 12 - So, Jul 19
Multiple Airlines Logo
3:20 pm - 2:20 pm
MDW
-
SXM
22h 00m
1 stop
Multiple Airlines Logo
3:20 pm - 9:40 am
SXM
-
MDW
19h 20m
1 stop
$635Multiple Airlines
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 $394, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$130
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 8424 reviews
7.8Entertainment
8.5Crew
8.1Boarding
7.9Comfort
7.2Food
Airline reviews

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

2.0 MediocreGregory, Apr 2026
TPA - CVG
Read more Delta reviews

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

The flight was way too HOT! And the plane did not have any in-flight TV entertainment.

Boarding was good. The flight was on time ( arrival was 20 minutes early). Inflight service was average ( US airlines have not mastered the skills of customer service yet). The food was mediocre. “ breakfast “ was downright awful and insulting. It was a piece of dough with mon descript filling that was supposed to be cheese omelette).

The tray table was broken and the food was terrible.

The gentleman at the gate I think his name is RIE was exceptional

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)