MDW - SXM

$411 Find Cheap Flights from Chicago Midway Airport to Simpson Bay

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Simpson Bay departing on 6/6. 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

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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Flights Deals

Cheap Flights from Midway to Simpson Bay

 
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.

Recent round-trip flight deals from Midway to Simpson Bay

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to Simpson Bay.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
9:12 pm - 11:23 amMDW-SXM
13h 11m1 stop
Frontier Logo
12:36 pm - 8:17 pmSXM-MDW
8h 41m1 stop
$411Frontier
Find Deal
Fri, Jun 6 - Sat, Jun 14
Frontier Logo
6:10 am - 5:02 pmMDW-SXM
9h 52m2 stops
Frontier Logo
12:36 pm - 8:17 pmSXM-MDW
8h 41m1 stop
$438Frontier
Find Deal
Sat, May 31 - Sat, Jun 14
Frontier Logo
6:20 am - 5:16 pmMDW-SXM
9h 56m2 stops
Frontier Logo
12:36 pm - 8:17 pmSXM-MDW
8h 41m1 stop
$475Frontier
Find Deal
Sat, Jun 21 - Sat, Jun 28
Frontier Logo
6:20 am - 5:16 pmMDW-SXM
9h 56m2 stops
Frontier Logo
12:36 pm - 8:17 pmSXM-MDW
8h 41m1 stop
$482Frontier
Find Deal
Sat, Jun 14 - Sat, Jun 21
Frontier Logo
6:20 am - 5:16 pmMDW-SXM
9h 56m2 stops
Frontier Logo
12:36 pm - 8:17 pmSXM-MDW
8h 41m1 stop
$484Frontier
Find Deal
Sat, Jun 14 - Sat, Jun 21
Frontier Logo
6:20 am - 5:16 pmMDW-SXM
9h 56m2 stops
Frontier Logo
12:36 pm - 8:17 pmSXM-MDW
8h 41m1 stop
$497Frontier
Find Deal
Sat, Jun 14 - Sat, Jun 21
Frontier Logo
9:12 pm - 5:04 pmMDW-SXM
18h 52m2 stops
Frontier Logo
12:36 pm - 8:17 pmSXM-MDW
8h 41m1 stop
$602Frontier
Find Deal
Fri, Jun 6 - Sat, Jun 14
Frontier Logo
9:12 pm - 5:04 pmMDW-SXM
18h 52m2 stops
Frontier Logo
12:36 pm - 8:17 pmSXM-MDW
8h 41m1 stop
$607Frontier
Find Deal
Fri, Jun 6 - Sat, Jun 14
Logo
9:20 am - 1:00 pmMDW-SXM
26h 40m2 stops
Logo
3:40 pm - 5:40 pmSXM-MDW
27h 00m3 stops
$3,494
Find Deal
Mon, Jun 2 - Mon, Jun 9
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Good to know

Cheapest flight$411
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 $518 for a one-way ticket and $411 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.

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

Information on your arrival and departure airports

Simpson Bay (SXM)
Chicago Midway Airport (MDW)

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