$185 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 4/10. 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 the Cayman Islands

Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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

Thu, May 7 - Tue, May 12
Multiple Airlines Logo
6:00 am - 9:15 pm
MDW
-
GCM
15h 15m
2 stops
Multiple Airlines Logo
11:30 am - 10:02 pm
GCM
-
MDW
10h 32m
2 stops
$496Multiple Airlines
Sat, Apr 4 - Thu, Apr 9
Multiple Airlines Logo
6:30 am - 2:50 pm
MDW
-
GCM
8h 20m
2 stops
Multiple Airlines Logo
4:25 pm - 3:20 pm
GCM
-
MDW
22h 55m
1 stop
$535Multiple Airlines
Mon, Mar 30 - Mon, Apr 6
Multiple Airlines Logo
9:42 pm - 4:05 pm
MDW
-
GCM
18h 23m
1 stop
Multiple Airlines Logo
7:00 am - 8:07 pm
GCM
-
MDW
37h 07m
2 stops
$545Multiple Airlines
Tue, Apr 28 - Mon, May 4
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 12:05 am
GCM
-
MDW
11h 00m
1 stop
$547Southwest
Tue, Apr 28 - Mon, May 4
Southwest Logo
8:55 pm - 12:10 pm
MDW
-
GCM
15h 15m
2 stops
Southwest Logo
1:05 pm - 10:20 pm
GCM
-
MDW
9h 15m
2 stops
$552Southwest
Fri, May 29 - Tue, Jun 2
Multiple Airlines Logo
10:25 am - 12:45 pm
MDW
-
GCM
26h 20m
1 stop
Multiple Airlines Logo
11:30 am - 10:02 pm
GCM
-
MDW
10h 32m
2 stops
$561Multiple Airlines
Fri, May 29 - Tue, Jun 2
Multiple Airlines Logo
10:25 am - 12:45 pm
MDW
-
GCM
26h 20m
1 stop
Multiple Airlines Logo
1:45 pm - 2:35 pm
GCM
-
MDW
24h 50m
1 stop
$563Multiple Airlines
Sat, Apr 4 - Thu, Apr 9
Southwest Logo
9:35 pm - 12:00 pm
MDW
-
GCM
14h 25m
2 stops
Southwest Logo
1:05 pm - 11:55 pm
GCM
-
MDW
10h 50m
2 stops
$573Southwest
Sat, May 2 - Sat, May 9
Southwest Logo
7:45 am - 3:00 pm
MDW
-
GCM
7h 15m
1 stop
Southwest Logo
1:05 pm - 10:35 pm
GCM
-
MDW
9h 30m
1 stop
$579Southwest
Thu, Apr 9 - Thu, May 28
Southwest Logo
9:35 pm - 12:10 pm
MDW
-
GCM
14h 35m
2 stops
Southwest Logo
1:05 pm - 10:20 pm
GCM
-
MDW
9h 15m
2 stops
$582Southwest
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 20m.

Find deals

Good to know

Cheapest flight$163
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)