MDW - SXM

$244 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 9/25. 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

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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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

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
$375Frontier
Find Deal
Sat, Jan 10 - Sat, Jan 17
Frontier Logo
6:00 am - 3:20 pmMDW-SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:26 pmSXM-MDW
8h 56m1 stop
$439Frontier
Find Deal
Sat, Jan 3 - Sat, Jan 10
Frontier Logo
6:00 am - 3:20 pmMDW-SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pmSXM-MDW
8h 55m1 stop
$568Frontier
Find Deal
Sat, Feb 28 - Thu, Mar 5
Delta Logo
4:30 pm - 12:15 pmMDW-SXM
17h 45m2 stops
Delta Logo
1:45 pm - 9:46 pmSXM-MDW
10h 01m1 stop
$624Delta
Find Deal
Wed, Jan 28 - Sun, Feb 1
Delta Logo
6:00 am - 2:56 pmMDW-SXM
6h 56m1 stop
Delta Logo
1:45 pm - 9:46 pmSXM-MDW
10h 01m1 stop
$632Delta
Find Deal
Tue, Mar 3 - Wed, Mar 4
Delta Logo
6:00 am - 2:56 pmMDW-SXM
6h 56m1 stop
Delta Logo
4:26 pm - 12:35 pmSXM-MDW
22h 09m2 stops
$679Delta
Find Deal
Wed, Nov 5 - Tue, Nov 11
Multiple Airlines Logo
11:00 am - 3:21 pmMDW-SXM
26h 21m1 stop
Multiple Airlines Logo
4:20 pm - 9:12 amSXM-MDW
42h 52m2 stops
$811Multiple Airlines
Find Deal
Wed, Nov 5 - Tue, Nov 11
Multiple Airlines Logo
11:00 am - 3:21 pmMDW-SXM
26h 21m1 stop
Multiple Airlines Logo
4:20 pm - 10:05 amSXM-MDW
19h 45m1 stop
$817Multiple Airlines
Find Deal
Thu, Nov 6 - Thu, Nov 13
WestJet Logo
9:20 am - 3:21 pmMDW-SXM
28h 01m2 stops
WestJet Logo
4:20 pm - 6:18 pmSXM-MDW
27h 58m3 stops
$1,142WestJet
Find Deal
Thu, Nov 6 - Thu, Nov 13
WestJet Logo
9:20 am - 3:21 pmMDW-SXM
28h 01m2 stops
WestJet Logo
4:20 pm - 6:18 pmSXM-MDW
27h 58m3 stops
$1,143WestJet
Find Deal

Everything you should know

Top airlines
Frontier
Cheapest • from $375 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$375
Frontier
Sat 1/24Sat 1/31
MDW - SXM • 1 stop
Cheapest one-way
$244
Multiple Airlines
Thu 9/25
MDW - SXM • 2 stops
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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!
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 Frontier ($375) and Delta ($624).

Find deals

Good to know

Cheapest flight$244
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 $244 for a one-way ticket and $375 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 7954 reviews
7.9Entertainment
8.2Boarding
7.9Comfort
8.5Crew
7.3Food
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

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)

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