$293 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 7/30. 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

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Flights Deals

Best St. Maarten Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Simpson Bay
Simpson Bay1 stop$471
Simpson Bay
Simpson Bay1 stop$471

Cheap Flights from Midway to St. Maarten

 
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

Fri, Sep 26 - Sat, Oct 4
Frontier Logo
8:34 am - 12:25 pmMDW-SXM
26h 51m1 stop
Frontier Logo
1:58 pm - 7:39 amSXM-MDW
18h 41m1 stop
$471Frontier
Find Deal
Fri, Jun 27 - Sat, Jul 5
Frontier Logo
9:12 pm - 11:26 amMDW-SXM
13h 14m1 stop
Frontier Logo
12:36 pm - 8:22 pmSXM-MDW
8h 46m1 stop
$508Frontier
Find Deal
Wed, Jun 25 - Sun, Jun 29
 Logo
5:50 pm - 1:15 pmMDW-SXM
18h 25m1 stop
 Logo
2:10 pm - 8:45 amSXM-MDW
19h 35m1 stop
Fri, Jun 27 - Sun, Jun 29
 Logo
9:12 pm - 2:00 pmMDW-SXM
15h 48m2 stops
 Logo
2:10 pm - 8:45 amSXM-MDW
19h 35m1 stop
Thu, Jun 26 - Sun, Jun 29
 Logo
9:12 pm - 2:00 pmMDW-SXM
15h 48m2 stops
 Logo
2:10 pm - 8:45 amSXM-MDW
19h 35m1 stop
Thu, Jun 26 - Sun, Jun 29
 Logo
9:12 pm - 2:00 pmMDW-SXM
15h 48m2 stops
 Logo
2:10 pm - 8:45 amSXM-MDW
19h 35m1 stop
Sat, Nov 15 - Sat, Nov 22
Delta Logo
6:00 am - 2:35 pmMDW-SXM
6h 35m1 stop
Delta Logo
4:00 pm - 9:44 pmSXM-MDW
7h 44m1 stop
$727Delta
Find Deal
Thu, Dec 4 - Sat, Dec 13
Delta Logo
6:00 am - 2:35 pmMDW-SXM
6h 35m1 stop
Delta Logo
4:00 pm - 9:44 pmSXM-MDW
7h 44m1 stop
$767Delta
Find Deal
Wed, Jun 25 - Thu, Jul 3
WestJet Logo
9:21 am - 1:15 pmMDW-SXM
26h 54m2 stops
WestJet Logo
3:10 pm - 9:45 pmSXM-MDW
31h 35m2 stops
$3,201WestJet
Find Deal
Wed, Jun 25 - Thu, Jul 3
WestJet Logo
1:47 pm - 1:15 pmMDW-SXM
22h 28m2 stops
WestJet Logo
3:10 pm - 5:40 pmSXM-MDW
27h 30m2 stops
$3,246WestJet
Find Deal
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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 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 Frontier ($471) and Delta ($727).


Good to know

Cheapest flight$293
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.

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.
8.0
DeltaOverall score based on 7963 reviews
7.9Entertainment
8.2Boarding
7.3Food
8.5Crew
7.9Comfort
Airline reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

4.0 OkayKoonj, Jun 2025MSP - AUS
Read more Delta reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Overall, aside from the baggage issue, it was as good as one expects.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

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

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