$115 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 3/2. 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

Mon, Mar 9 - Sat, Mar 14
Multiple Airlines Logo
11:00 am - 11:15 am
MDW
-
SXM
23h 15m
1 stop
Multiple Airlines Logo
2:20 pm - 10:19 pm
SXM
-
MDW
32h 59m
2 stops
$536Multiple Airlines
Tue, Mar 3 - Wed, Mar 18
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m
1 stop
Delta Logo
12:55 pm - 10:31 pm
SXM
-
MDW
10h 36m
1 stop
$571Delta
Sat, Feb 21 - Sat, Feb 28
Delta Logo
6:00 am - 4:00 pm
MDW
-
SXM
8h 00m
1 stop
Delta Logo
1:38 pm - 10:31 pm
SXM
-
MDW
10h 53m
1 stop
$585Delta
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
$598Delta
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
$600Delta
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
Tue, Mar 24 - Tue, Mar 31
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
$611Delta
Fri, Apr 24 - Tue, Apr 28
Southwest Logo
5:35 am - 1:40 pm
MDW
-
SXM
7h 05m
1 stop
Southwest Logo
2:35 pm - 7:35 am
SXM
-
MDW
18h 00m
2 stops
$613Southwest
Wed, Mar 18 - Wed, Mar 25
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
$615Delta
Tue, Mar 24 - Tue, Mar 31
Delta Logo
9:35 am - 11:29 am
MDW
-
SXM
24h 54m
2 stops
Delta Logo
12:55 pm - 10:31 pm
SXM
-
MDW
10h 36m
1 stop
$616Delta
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.

Good to know

Cheapest flight$115
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 8173 reviews
7.8Entertainment
7.2Food
8.1Boarding
7.9Comfort
8.5Crew
Airline reviews

Only freetext wifi was available in flight; browsing WiFi required payment. Since the seats had no in flight entertainment, Delta should revisit this policy on this longer flight.

6.0 GoodEmily, Feb 2026
ATL - DAL
Read more Delta reviews

Only freetext wifi was available in flight; browsing WiFi required payment. Since the seats had no in flight entertainment, Delta should revisit this policy on this longer flight.

Only water, tea or coffee served midflight, even to comfort seating. Man next to me needed two seats and took up a portion of my seat and Delta did nothing.

The flight was great as well as the airline staff

First class and monitors weren’t working for mine & my husbands. Eventually fixed, but quite annoyed as we bought first class. Also, No foot rests.

Prior to takeoff, the pilot told us there was a possibility of not being able to land and going to Portland. Well that happened, we took off and then did 8 loops around Spokane before the pilot told us we ran out of fuel and had to go to Portland. So for a 35 minute flight we have now been on the plane for 3 hours (boarded at 6:50 am and landed in Portland at 10:30). Then, we just sat in Portland's airport with no updates of when we can start heading back. All of a sudden, our pilots and crew just left, leaving us stranded in a different city and state. We continued to sit in Portland until we finally got a new crew assigned and boarded the plane (This was from 10:30-2). We then sat on the plane for an additional hour before take off because they had to count us multiple times. We finally landed in Spokane at 3:55 PM. So a flight that should have taken at max an hour took us 10 hours and we missed the majority of the recruiting event we went for.

It was delayed but other than that it was great.

Got on the plane and sat there for an hour before departure.

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

They double booked seats, the gate staff changed my ticket as I was boarding she went over to the computer and changed it without telling me. She messed up an entire three row section for me and others. Other travelers were outraged but the gate staff were so rude, so condescending saying it wasn't their problem to solve. I would rate this a zero if I could. Will not fly Delta again I'll stick with United and American.

It was nt delta. It was aeromexo. Service was awful. They served a very small drink and NO snack for a 3hr and 35min flight. Then for the first 30 min of the flight is was talk and talk over head interruption the movie/ show i picked to watch.

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

Information on your arrival and departure airports