MDW - SXM

$216 Find Cheap Flights from Chicago Midway Airport to Simpson Bay

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 Simpson Bay departing on 5/5. 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 Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Simpson Bay, 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 Simpson Bay, as well as popular online travel agencies
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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$521
Southwest
Wed 4/22Thu 4/30
MDW - SXM • 1 stop
Cheapest one-way
$216
Southwest
Tue 5/5
MDW - SXM • 1 stop
Top airlines
Southwest
Cheapest • from $521 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Midway and Simpson Bay. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Orlando (MCO)
Cheapest • Avg $752 (round-trip)
Atlanta (ATL)
Shortest trip • 6h 49m (one-way)
Insights
Insights
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Simpson Bay (MDW-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Simpson Bay 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 Simpson Bay

Wed, Apr 22 - Thu, Apr 30
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
$521Southwest
Sat, Apr 4 - Sat, Apr 11
Frontier Logo
6:40 am - 3:15 pm
MDW
-
SXM
7h 35m
1 stop
Frontier Logo
4:20 pm - 8:07 pm
SXM
-
MDW
28h 47m
1 stop
$525Frontier
Tue, Apr 28 - Tue, May 5
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
$526Southwest
Wed, Apr 22 - Thu, Apr 30
Southwest Logo
6:00 am - 1:30 pm
MDW
-
SXM
6h 30m
1 stop
Southwest Logo
2:25 pm - 7:10 am
SXM
-
MDW
17h 45m
2 stops
$544Southwest
Mon, May 11 - Sat, May 16
Southwest Logo
5:35 am - 1:30 pm
MDW
-
SXM
6h 55m
1 stop
Southwest Logo
1:20 pm - 10:35 pm
SXM
-
MDW
10h 15m
1 stop
$593Southwest
Mon, Apr 27 - Mon, May 4
Southwest Logo
5:35 am - 1:30 pm
MDW
-
SXM
6h 55m
1 stop
Southwest Logo
2:25 pm - 7:35 am
SXM
-
MDW
18h 10m
2 stops
$598Southwest
Wed, Apr 15 - Mon, Apr 20
Southwest Logo
8:55 pm - 1:30 pm
MDW
-
SXM
15h 35m
2 stops
Southwest Logo
2:25 pm - 7:35 am
SXM
-
MDW
18h 10m
2 stops
$616Southwest
Sun, Aug 16 - Fri, Aug 21
Southwest Logo
5:10 am - 1:40 pm
MDW
-
SXM
7h 30m
1 stop
Southwest Logo
2:45 pm - 10:40 pm
SXM
-
MDW
8h 55m
1 stop
$619Southwest
Sun, Aug 16 - Fri, Aug 21
Southwest Logo
5:10 am - 1:40 pm
MDW
-
SXM
7h 30m
1 stop
Southwest Logo
2:45 pm - 7:35 am
SXM
-
MDW
17h 50m
2 stops
$624Southwest
Sat, Apr 11 - Fri, Apr 17
Southwest Logo
5:15 am - 1:40 pm
MDW
-
SXM
7h 25m
1 stop
Southwest Logo
2:25 pm - 12:05 am
SXM
-
MDW
10h 40m
1 stop
$638Southwest
Booking Insights

KAYAK's insights & trends for Midway to Simpson Bay flights

Get data-powered insights and trends into flights from Midway to Simpson Bay 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 Simpson Bay?

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 Simpson Bay were found on Southwest ($521) and Frontier ($525).

Find deals

Good to know

Cheapest flight$216
Flight from Chicago Midway Airport to Simpson Bay

When to book flights from Midway to Simpson Bay

Are your dates flexible? Find out the best times to travel from Midway to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Simpson Bay flights

  • What is the cheapest flight from Chicago Midway Airport to Simpson Bay?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Simpson Bay was $216 for a one-way ticket and $521 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Simpson Bay?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago Midway Airport and on arrival in Simpson Bay.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Simpson Bay?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Simpson Bay?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Simpson Bay.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Simpson Bay?

    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 Simpson Bay.

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

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

    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 to Simpson Bay with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Simpson Bay?

    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 to Simpson Bay from Chicago Midway Airport 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 Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Simpson Bay. 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 Simpson Bay? 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 8288 reviews
8.5Crew
8.1Boarding
7.8Entertainment
7.9Comfort
7.2Food
Airline reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

10.0 ExcellentDebra, Mar 2026
PBI - ATL
Read more Delta reviews

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Everything you need to know for your flight from Midway to Simpson Bay

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Simpson Bay (SXM)