$188 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 5/31. 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

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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

Mon, May 25 - Sun, May 31
Multiple Airlines Logo
10:30 am - 12:45 pm
MDW
-
GCM
26h 15m
1 stop
Multiple Airlines Logo
4:45 pm - 10:02 pm
GCM
-
MDW
29h 17m
2 stops
$566Multiple Airlines
Tue, Jul 14 - Wed, Jul 22
Southwest Logo
5:10 am - 11:50 am
MDW
-
GCM
6h 40m
1 stop
Southwest Logo
12:45 pm - 10:00 pm
GCM
-
MDW
9h 15m
1 stop
$579Southwest
Tue, Jul 14 - Wed, Jul 22
Southwest Logo
5:10 am - 11:50 am
MDW
-
GCM
6h 40m
1 stop
Southwest Logo
12:45 pm - 11:50 pm
GCM
-
MDW
11h 05m
2 stops
$584Southwest
Fri, Jul 10 - Wed, Jul 15
Multiple Airlines Logo
3:20 pm - 12:45 pm
MDW
-
GCM
21h 25m
1 stop
Multiple Airlines Logo
11:30 am - 10:08 pm
GCM
-
MDW
10h 38m
2 stops
$594Multiple Airlines
Mon, Jun 1 - Thu, Jun 4
Southwest Logo
9:25 pm - 12:10 pm
MDW
-
GCM
14h 45m
2 stops
Southwest Logo
12:50 pm - 9:25 pm
GCM
-
MDW
8h 35m
1 stop
$598Southwest
Fri, Jun 5 - Tue, Jun 9
Delta Logo
6:23 am - 11:54 am
MDW
-
GCM
5h 31m
1 stop
Delta Logo
12:59 pm - 10:17 pm
GCM
-
MDW
9h 18m
1 stop
$599Delta
Sat, Jul 4 - Sat, Jul 11
Southwest Logo
6:20 am - 12:10 pm
MDW
-
GCM
5h 50m
1 stop
Southwest Logo
1:05 pm - 10:25 pm
GCM
-
MDW
9h 20m
1 stop
$604Southwest
Mon, Jun 1 - Fri, Jun 5
Multiple Airlines Logo
10:15 am - 12:45 pm
MDW
-
GCM
26h 30m
1 stop
Multiple Airlines Logo
7:00 am - 10:02 pm
GCM
-
MDW
15h 02m
2 stops
$606Multiple Airlines
Mon, Jun 1 - Thu, Jun 4
Delta Logo
6:23 am - 11:54 am
MDW
-
GCM
5h 31m
1 stop
Delta Logo
1:19 pm - 9:09 pm
GCM
-
MDW
7h 50m
1 stop
$607Delta
Sat, Jul 4 - Wed, Jul 8
Southwest Logo
6:20 am - 12:10 pm
MDW
-
GCM
5h 50m
1 stop
Southwest Logo
12:45 pm - 11:50 pm
GCM
-
MDW
11h 05m
2 stops
$608Southwest
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.

How long does a flight from Chicago Midway Airport to the Cayman Islands take?

The duration of a flight to the Cayman Islands depends on your arrival airport. The shortest route to the Cayman Islands from Chicago Midway Airport is to George Town, which takes 5h 31m.

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Good to know

Cheapest flight$188
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.

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)