$147 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 1/24. 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
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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$367
Simpson Bay
Simpson Bay1 stop$367

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, Feb 7
Frontier Logo
6:00 am - 3:20 pmMDW-SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pmSXM-MDW
8h 55m1 stop
$367Frontier
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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
$375Frontier
Find Deal
Sat, Jan 17 - Sat, Jan 24
Frontier Logo
6:00 am - 3:20 pmMDW-SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pmSXM-MDW
8h 55m1 stop
$455Frontier
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Fri, Jan 23 - Sat, Jan 31
Frontier Logo
8:56 pm - 3:20 pmMDW-SXM
16h 24m2 stops
Frontier Logo
4:30 pm - 11:25 pmSXM-MDW
8h 55m1 stop
$467Frontier
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Wed, Nov 26 - Wed, Dec 3
Delta Logo
6:00 am - 2:55 pmMDW-SXM
6h 55m1 stop
Delta Logo
4:17 pm - 11:32 pmSXM-MDW
9h 15m1 stop
$607Delta
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Sun, Nov 30 - Sun, Dec 7
Logo
11:00 am - 3:21 pmMDW-SXM
26h 21m1 stop
Logo
4:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
$617
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Thu, Nov 27 - Thu, Dec 4
Delta Logo
6:00 am - 2:55 pmMDW-SXM
6h 55m1 stop
Delta Logo
4:17 pm - 11:32 pmSXM-MDW
9h 15m1 stop
$632Delta
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Sun, Nov 30 - Sun, Dec 7
Logo
7:02 pm - 3:21 pmMDW-SXM
42h 19m2 stops
Logo
4:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
$675
Find Deal
Sun, Nov 30 - Sun, Dec 7
WestJet Logo
9:41 am - 3:21 pmMDW-SXM
27h 40m2 stops
WestJet Logo
4:20 pm - 1:08 pmSXM-MDW
22h 48m2 stops
$948WestJet
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Sat, Nov 1 - Thu, Nov 6
WestJet Logo
3:00 pm - 3:21 pmMDW-SXM
23h 21m2 stops
WestJet Logo
4:20 pm - 1:08 pmSXM-MDW
22h 48m2 stops
$3,135WestJet
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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 $305, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$147
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 7960 reviews
7.9Comfort
8.2Boarding
8.5Crew
7.3Food
7.9Entertainment
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

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

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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