$387 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 9/2. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Saint Martin Island

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Simpson Bay
Simpson Bay1 stop$522
Simpson Bay
Simpson Bay1 stop$522

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

Wed, Oct 29 - Wed, Nov 5
 Logo
4:15 pm - 2:21 pmMDW-SXM
21h 06m1 stop
 Logo
4:28 pm - 4:45 pmSXM-MDW
50h 17m2 stops
Mon, Oct 20 - Fri, Oct 31
Delta Logo
6:00 am - 1:49 pmMDW-SXM
6h 49m1 stop
Delta Logo
3:14 pm - 12:31 pmSXM-MDW
22h 17m2 stops
$587Delta
Find Deal
Mon, Oct 20 - Fri, Oct 31
Delta Logo
6:00 am - 1:49 pmMDW-SXM
6h 49m1 stop
Delta Logo
3:14 pm - 10:14 pmSXM-MDW
8h 00m1 stop
$597Delta
Find Deal
Mon, Nov 3 - Tue, Nov 11
 Logo
9:32 am - 3:21 pmMDW-SXM
27h 49m2 stops
 Logo
4:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
Mon, Nov 3 - Tue, Nov 11
 Logo
4:15 pm - 3:21 pmMDW-SXM
21h 06m1 stop
 Logo
4:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
Sat, Jan 24 - Sun, Feb 1
Delta Logo
6:00 am - 2:56 pmMDW-SXM
6h 56m1 stop
Delta Logo
1:45 pm - 9:46 pmSXM-MDW
10h 01m1 stop
$777Delta
Find Deal
Fri, Jan 23 - Sat, Jan 31
Delta Logo
6:00 am - 2:56 pmMDW-SXM
6h 56m1 stop
Delta Logo
1:45 pm - 9:46 pmSXM-MDW
10h 01m1 stop
$817Delta
Find Deal
Mon, Nov 3 - Tue, Nov 11
WestJet Logo
1:48 pm - 3:21 pmMDW-SXM
23h 33m2 stops
WestJet Logo
4:20 pm - 1:07 pmSXM-MDW
22h 47m2 stops
$3,057WestJet
Find Deal
Wed, Nov 5 - Tue, Nov 11
WestJet Logo
1:48 pm - 3:21 pmMDW-SXM
23h 33m2 stops
WestJet Logo
4:20 pm - 1:07 pmSXM-MDW
22h 47m2 stops
$3,145WestJet
Find Deal
Wed, Dec 10 - Tue, Dec 16
WestJet Logo
10:35 am - 3:21 pmMDW-SXM
26h 46m2 stops
WestJet Logo
4:20 pm - 6:07 pmSXM-MDW
27h 47m2 stops
$3,199WestJet
Find Deal
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 $318, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight$387
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 7977 reviews
7.9Comfort
8.2Boarding
7.3Food
7.9Entertainment
8.5Crew
Airline reviews

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

4.0 Okaypuravi, Aug 2025LGA - STL
Read more Delta reviews

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.