$171 Find Cheap Flights from Chicago Midway Airport to Cayman Islands

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 the Cayman Islands departing on 1/21. 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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Cheap Flights from Midway to the Cayman Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town2 stops$450
George Town
George Town2 stops$450

Book Cheap Midway to the Cayman Islands Plane Tickets

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

Sun, Dec 7 - Fri, Dec 12
Southwest Logo
9:40 pm - 12:35 pmMDW-GCM
13h 55m2 stops
Southwest Logo
1:30 pm - 12:10 amGCM-MDW
11h 40m2 stops
$450Southwest
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Tue, Jan 20 - Thu, Jan 29
Delta Logo
6:00 am - 12:35 pmMDW-GCM
5h 35m1 stop
Delta Logo
2:00 pm - 9:46 pmGCM-MDW
8h 46m1 stop
$452Delta
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Tue, Jan 20 - Thu, Jan 29
Southwest Logo
7:50 pm - 12:55 pmMDW-GCM
16h 05m2 stops
Southwest Logo
1:50 pm - 9:00 pmGCM-MDW
8h 10m1 stop
$467Southwest
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Mon, Dec 15 - Fri, Dec 19
Southwest Logo
5:05 am - 12:35 pmMDW-GCM
6h 30m1 stop
Southwest Logo
1:30 pm - 7:15 pmGCM-MDW
6h 45m1 stop
$483Southwest
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Mon, Dec 15 - Fri, Dec 19
Southwest Logo
5:15 pm - 12:35 pmMDW-GCM
18h 20m2 stops
Southwest Logo
1:30 pm - 8:35 pmGCM-MDW
8h 05m1 stop
$487Southwest
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Sun, Dec 7 - Fri, Dec 12
Southwest Logo
5:50 am - 12:35 pmMDW-GCM
5h 45m1 stop
Southwest Logo
1:30 pm - 6:55 pmGCM-MDW
6h 25m1 stop
$491Southwest
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Tue, Dec 9 - Tue, Dec 16
Multiple Airlines Logo
8:00 am - 4:05 pmMDW-GCM
7h 05m1 stop
Multiple Airlines Logo
7:00 am - 3:30 pmGCM-MDW
9h 30m1 stop
$493Multiple Airlines
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Wed, Jan 21 - Sun, Jan 25
Southwest Logo
5:00 am - 12:55 pmMDW-GCM
6h 55m1 stop
Southwest Logo
1:50 pm - 5:05 amGCM-MDW
16h 15m2 stops
$510Southwest
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Mon, Sep 29 - Fri, Oct 3
Delta Logo
6:00 am - 11:36 amMDW-GCM
5h 36m1 stop
Delta Logo
12:52 pm - 9:36 pmGCM-MDW
8h 44m1 stop
$514Delta
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Mon, Sep 29 - Fri, Oct 3
Delta Logo
6:00 am - 11:36 amMDW-GCM
5h 36m1 stop
Delta Logo
12:52 pm - 8:40 amGCM-MDW
19h 48m2 stops
$518Delta
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Booking Insights

KAYAK's insights & trends for Midway to the Cayman Islands flights

Get data-powered insights and trends into flights from Midway to the Cayman Islands 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 the Cayman Islands?

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 the Cayman Islands were found on Southwest ($450) and Delta ($452).

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Good to know

Cheapest flight$171
Flight from Chicago Midway Airport to George Town

FAQs - booking Cayman Islands flights

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

    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 Cayman Islands.

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

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

    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 Cayman Islands 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 Cayman Islands?

    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 Cayman Islands 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 the Cayman Islands?

    The cheapest time of day to fly to the Cayman Islands is generally in the morning, when round-trip flights cost $615 on average. The most expensive time of day to fly to the Cayman Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $615.

Everything you need to know for your flight from Midway to the Cayman Islands

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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