$264 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

Sun, Feb 15 - Fri, Feb 20
Multiple Airlines Logo
4:15 pm - 3:17 pm
MDW
-
SXM
21h 02m1 stop
Multiple Airlines Logo
3:20 pm - 2:55 pm
SXM
-
MDW
25h 35m2 stops
$471Multiple Airlines
Sun, Feb 8 - Tue, Feb 10
Delta Logo
6:00 am - 2:55 pm
MDW
-
SXM
6h 55m1 stop
Delta Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
$501Delta
Sun, Feb 8 - Wed, Feb 11
Delta Logo
10:48 am - 12:30 pm
MDW
-
SXM
23h 42m2 stops
Delta Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
$506Delta
Sat, Mar 14 - Sat, Mar 21
Frontier Logo
6:00 am - 2:20 pm
MDW
-
SXM
7h 20m1 stop
Frontier Logo
3:41 pm - 7:47 pm
SXM
-
MDW
29h 06m1 stop
$508Frontier
Fri, Feb 6 - Wed, Feb 11
Delta Logo
7:16 pm - 2:17 pm
MDW
-
SXM
17h 01m1 stop
Delta Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
$531Delta
Fri, Feb 6 - Thu, Feb 12
Delta Logo
6:14 pm - 12:30 pm
MDW
-
SXM
16h 16m2 stops
Delta Logo
1:38 pm - 10:31 pm
SXM
-
MDW
10h 53m1 stop
$536Delta
Fri, Jan 23 - Sat, Jan 31
Delta Logo
6:00 am - 2:55 pm
MDW
-
SXM
6h 55m1 stop
Delta Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
$561Delta
Sat, Jan 24 - Sat, Jan 31
Delta Logo
6:25 am - 4:03 pm
MDW
-
SXM
7h 38m1 stop
Delta Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
$601Delta
Mon, Apr 13 - Thu, Apr 16
Delta Logo
5:31 pm - 12:18 pm
MDW
-
SXM
17h 47m2 stops
Delta Logo
3:35 pm - 4:36 pm
SXM
-
MDW
26h 01m2 stops
$611Delta
Sat, Jan 24 - Mon, Feb 2
Delta Logo
6:25 am - 4:03 pm
MDW
-
SXM
7h 38m1 stop
Delta Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
$641Delta
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 $400, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight$264
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.

  • What is the cheapest time of day to fly to Saint Martin Island?

    The cheapest time of day to fly to Saint Martin Island is generally in the morning, when round-trip flights cost $609 on average. The most expensive time of day to fly to Saint Martin Island is generally in the morning, which is peak travel time and where the average cost of a ticket is $609.

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 8018 reviews
7.9Comfort
8.1Boarding
7.9Entertainment
8.5Crew
7.3Food
Airline reviews

Did not realize internet screen was hidden between seats and no info printed!!!!

6.0 GoodAnonymous, Dec 2025
BOS - MSP
Read more Delta reviews

Did not realize internet screen was hidden between seats and no info printed!!!!

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

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

Information on your arrival and departure airports