$176 Find Cheap Flights from Chicago Midway Airport to St. Maarten

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 St. Maarten departing on 12/14. 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

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Book Cheap Midway to St. Maarten 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 St. Maarten 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 St. Maarten

Thu, Dec 11 - Wed, Dec 17
Delta Logo
6:00 am - 2:28 pmMDW-SXM
6h 28m1 stop
Delta Logo
3:53 pm - 11:47 pmSXM-MDW
9h 54m1 stop
$375Delta
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Sun, Nov 23 - Tue, Nov 25
Delta Logo
6:48 pm - 2:55 pmMDW-SXM
18h 07m2 stops
Delta Logo
4:20 pm - 8:54 amSXM-MDW
18h 34m2 stops
$380Delta
Find Deal
Mon, Nov 10 - Fri, Nov 14
Delta Logo
6:00 am - 2:55 pmMDW-SXM
6h 55m1 stop
Delta Logo
4:20 pm - 11:40 pmSXM-MDW
9h 20m1 stop
$437Delta
Find Deal
Thu, Dec 11 - Wed, Dec 17
Delta Logo
6:00 am - 2:28 pmMDW-SXM
6h 28m1 stop
Delta Logo
3:53 pm - 11:47 pmSXM-MDW
9h 54m1 stop
$463Delta
Find Deal
Tue, Dec 16 - Thu, Jan 8
Delta Logo
6:00 am - 2:28 pmMDW-SXM
6h 28m1 stop
Delta Logo
1:55 pm - 10:09 pmSXM-MDW
10h 14m1 stop
$481Delta
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Tue, Dec 16 - Wed, Jan 7
Delta Logo
6:40 pm - 2:28 pmMDW-SXM
17h 48m2 stops
Delta Logo
4:20 pm - 10:34 amSXM-MDW
20h 14m2 stops
$486Delta
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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
$489Frontier
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Thu, Jan 8 - Thu, Jan 15
Multiple Airlines Logo
6:44 pm - 3:10 pmMDW-SXM
18h 26m2 stops
Multiple Airlines Logo
4:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
$523Multiple Airlines
Find Deal
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
$569Multiple Airlines
Find Deal
Sat, Dec 6 - Wed, Dec 10
WestJet Logo
9:59 am - 3:21 pmMDW-SXM
27h 22m3 stops
WestJet Logo
4:20 pm - 1:10 pmSXM-MDW
22h 50m3 stops
$905WestJet
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to St. Maarten flights

Get data-powered insights and trends into flights from Midway to St. Maarten to help you find the cheapest flights, the best time to fly and much more.

Which airlines fly non-stop between Chicago Midway Airport and St. Maarten?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Chicago Midway Airport to St. Maarten.

There is just one airline that flies from Chicago Midway Airport to St. Maarten direct and that is Delta. The best round-trip deal found from Delta for the route is to Simpson Bay (SXM) and costs $622.

Which airlines provide the cheapest flights from Chicago Midway Airport to St. Maarten?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to St. Maarten were found on Delta ($375) and Frontier ($489).

Good to know

Cheapest flight$181
Flight from Chicago Midway Airport to Simpson Bay

FAQs - booking St. Maarten flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to St. Maarten?

    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 St. Maarten.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to St. Maarten?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to St. Maarten 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 St. Maarten?

    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 St. Maarten 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 St. Maarten?

    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 St. Maarten 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 St. Maarten?

    The cheapest time of day to fly to St. Maarten is generally in the morning, when round-trip flights cost $609 on average. The most expensive time of day to fly to St. Maarten 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 St. Maarten

 
Need help choosing which airline to fly with from Midway to St. Maarten? 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 7992 reviews
7.3Food
8.5Crew
7.9Comfort
8.2Boarding
7.9Entertainment
Airline reviews

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.

8.0 ExcellentJulie, Oct 2025LAX - SFO
Read more Delta reviews

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

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Everything you need to know for your flight from Midway to St. Maarten

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