$138 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

Sat, Mar 7 - Sat, Mar 14
Frontier Logo
6:00 am - 3:20 pm
MDW
-
SXM
7h 20m
1 stop
Frontier Logo
2:35 pm - 10:09 pm
SXM
-
MDW
8h 34m
1 stop
$369Frontier
Sat, Mar 7 - Sat, Mar 14
Frontier Logo
6:00 am - 3:20 pm
MDW
-
SXM
7h 20m
1 stop
Frontier Logo
2:35 pm - 10:09 pm
SXM
-
MDW
8h 34m
1 stop
$404Frontier
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
8:50 pm - 1:30 pm
MDW
-
SXM
15h 40m
2 stops
Southwest Logo
2:25 pm - 7:35 am
SXM
-
MDW
18h 10m
2 stops
$478Southwest
Tue, Apr 14 - Tue, Apr 21
Multiple Airlines Logo
7:30 am - 8:30 am
MDW
-
SXM
24h 00m
2 stops
Multiple Airlines Logo
3:20 pm - 10:15 am
SXM
-
MDW
19h 55m
1 stop
$538Multiple Airlines
Fri, Mar 20 - Sat, Mar 28
Frontier Logo
9:51 pm - 1:30 pm
MDW
-
SXM
14h 39m
2 stops
Frontier Logo
2:35 pm - 10:09 pm
SXM
-
MDW
8h 34m
1 stop
$543Frontier
Sat, Mar 28 - Tue, Mar 31
Multiple Airlines Logo
9:16 pm - 1:30 pm
MDW
-
SXM
15h 14m
2 stops
Multiple Airlines Logo
3:20 pm - 10:15 am
SXM
-
MDW
19h 55m
1 stop
$601Multiple Airlines
Tue, Apr 28 - Fri, May 1
Southwest Logo
6:00 am - 1:30 pm
MDW
-
SXM
6h 30m
1 stop
Southwest Logo
2:25 pm - 12:05 am
SXM
-
MDW
10h 40m
1 stop
$605Southwest
Tue, Apr 28 - Fri, May 1
Southwest Logo
6:00 am - 1:30 pm
MDW
-
SXM
6h 30m
1 stop
Southwest Logo
2:25 pm - 12:15 pm
SXM
-
MDW
22h 50m
2 stops
$610Southwest
Tue, Mar 24 - Wed, Apr 1
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
$625Delta
Tue, Mar 24 - Wed, Apr 1
Delta Logo
1:10 pm - 11:29 am
MDW
-
SXM
21h 19m
2 stops
Delta Logo
12:55 pm - 10:31 pm
SXM
-
MDW
10h 36m
1 stop
$630Delta
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 $373, prices are generally cheapest when you fly direct.

Find deals

Good to know

Cheapest flight$138
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 8239 reviews
7.8Entertainment
8.5Crew
7.2Food
7.9Comfort
8.1Boarding
Airline reviews

2+hrs delay without any reason provided and a cramped flight

2.0 MediocreYogendra Kumar, Feb 2026
DTW - MDT
Read more Delta reviews

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

Delta has too many delays now days. It is 1:06 am now. I was supposed to land in Norfolk at 10:30 pm. I got re-booked through Detroit and I’m still in Detroit. I hope to be landed in Norfolk by 3am. I’ve been in airports for 12 hours as of right now. There is a weather delay now but most delays lately have been maintenance.

Very Very late. Subsequent flights left an hour before ours

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)