MDW - SXM

$92 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 2/17. 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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Everything you should know

Cheapest round-trip
$571
Delta
Wed 3/4Wed 3/11
MDW - SXM • 1 stop
Cheapest one-way
$92
Multiple Airlines
Tue 2/17
MDW - SXM • 2 stops
Top airlines
Delta
Cheapest • from $571 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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, Mar 4 - Wed, Mar 11
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m
1 stop
Delta Logo
12:55 pm - 10:31 pm
SXM
-
MDW
10h 36m
1 stop
$571Delta
Sat, Feb 21 - Sat, Feb 28
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m
1 stop
Delta Logo
5:25 pm - 9:54 am
SXM
-
MDW
18h 29m
1 stop
$576Delta
Mon, Apr 27 - Fri, May 1
Southwest Logo
5:35 am - 1:40 pm
MDW
-
SXM
7h 05m
1 stop
Southwest Logo
2:35 pm - 11:40 pm
SXM
-
MDW
10h 05m
1 stop
$588Southwest
Mon, Apr 27 - Fri, May 1
Southwest Logo
4:10 pm - 1:40 pm
MDW
-
SXM
20h 30m
2 stops
Southwest Logo
2:35 pm - 11:40 pm
SXM
-
MDW
10h 05m
1 stop
$593Southwest
Wed, Mar 11 - Mon, Mar 16
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
$601Delta
Tue, Feb 24 - Tue, Mar 3
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m
1 stop
Delta Logo
1:38 pm - 10:33 pm
SXM
-
MDW
10h 55m
1 stop
$610Delta
Tue, Mar 17 - Tue, Mar 24
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
$611Delta
Fri, Apr 24 - Tue, Apr 28
Southwest Logo
5:35 am - 1:40 pm
MDW
-
SXM
7h 05m
1 stop
Southwest Logo
2:35 pm - 7:35 am
SXM
-
MDW
18h 00m
2 stops
$613Southwest
Tue, Jun 23 - Thu, Jul 2
Delta Logo
6:00 am - 2:00 pm
MDW
-
SXM
7h 00m
1 stop
Delta Logo
3:25 pm - 12:30 pm
SXM
-
MDW
22h 05m
2 stops
$620Delta
Fri, Jun 5 - Tue, Jun 9
Southwest Logo
5:10 am - 2:00 pm
MDW
-
SXM
7h 50m
1 stop
Southwest Logo
3:00 pm - 10:00 pm
SXM
-
MDW
8h 00m
1 stop
$625Southwest
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 Delta ($571) and Southwest ($588).

Find deals

Good to know

Cheapest flight$92
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 $129 for a one-way ticket and $571 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 8130 reviews
7.2Food
8.5Crew
7.8Entertainment
7.9Comfort
8.1Boarding
Airline reviews

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

2.0 MediocreTodd, Jan 2026
IAH - ATL
Read more Delta reviews

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

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)