$161 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 12/15. 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, Jan 24 - Sat, Jan 31
Frontier Logo
6:00 am - 3:20 pmMDW-SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pmSXM-MDW
8h 55m1 stop
$369Frontier
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Fri, Nov 28 - Wed, Dec 3
Delta Logo
6:00 am - 2:55 pmMDW-SXM
6h 55m1 stop
Delta Logo
3:53 pm - 11:47 pmSXM-MDW
9h 54m1 stop
$375Delta
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Sat, Feb 21 - Sat, Feb 28
Frontier Logo
6:00 am - 3:20 pmMDW-SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pmSXM-MDW
8h 55m1 stop
$387Frontier
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Sat, Feb 14 - Sat, Feb 28
Frontier Logo
6:00 am - 3:20 pmMDW-SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pmSXM-MDW
8h 55m1 stop
$393Frontier
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Thu, Dec 11 - Wed, Dec 17
Multiple Airlines Logo
7:23 pm - 2:15 pmMDW-SXM
40h 52m2 stops
Multiple Airlines Logo
4:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
$489Multiple Airlines
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Fri, Dec 26 - Wed, Dec 31
Delta Logo
5:59 pm - 2:17 pmMDW-SXM
18h 18m1 stop
Delta Logo
1:45 pm - 10:22 pmSXM-MDW
10h 37m1 stop
$612Delta
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Wed, Jan 28 - Fri, Feb 6
Delta Logo
6:00 am - 2:55 pmMDW-SXM
6h 55m1 stop
Delta Logo
1:55 pm - 10:26 pmSXM-MDW
10h 31m1 stop
$614Delta
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Sat, Dec 6 - Wed, Dec 10
WestJet Logo
1:50 pm - 3:21 pmMDW-SXM
23h 31m2 stops
WestJet Logo
4:20 pm - 6:18 pmSXM-MDW
27h 58m3 stops
$736WestJet
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Sun, Jan 11 - Sun, Jan 18
WestJet Logo
1:49 pm - 3:21 pmMDW-SXM
23h 32m2 stops
WestJet Logo
4:20 pm - 1:09 pmSXM-MDW
22h 49m2 stops
$772WestJet
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Tue, Apr 14 - Fri, Apr 17
Southwest Logo
6:00 am - 1:40 pmMDW-SXM
6h 40m1 stop
Southwest Logo
2:35 pm - 7:55 amSXM-MDW
18h 20m2 stops
$950Southwest
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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 $378, prices are generally cheapest when you fly direct.

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Good to know

Cheapest flight$161
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 8003 reviews
7.3Food
7.9Entertainment
7.9Comfort
8.2Boarding
8.5Crew
Airline reviews

I truly love flying with Delta. They have always treated me with the upmost respect

10.0 ExcellentMAYRA, Nov 2025JFK - MIA
Read more Delta reviews

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)