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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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.

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 18m .

$231 CHEAP FLIGHTS from Chicago Midway to Cayman Islands

KAYAK searches hundreds of travel sites at once for deals on flights to the Cayman Islands

...and more

Travelers love KAYAK

41,299,237 searches in the past 7 days on KAYAK

Save 22% 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.

Flights Deals

Best Cayman Islands Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

One-wayRound-trip

George Town1 stop$542

Cheap Flight Deals from Midway to the Cayman Islands (MDW-KY0)

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.

Round-trip

One-way

Last minute

Recent round-trip flight deals from Midway to the Cayman Islands

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to the Cayman Islands.

Discover the best prices for you by selecting your travel dates on KAYAK.

5:05 am - 11:50 amMDW-GCM

6h 45m1 stop

12:45 pm - 11:00 pmGCM-MDW

10h 15m2 stops

$542Southwest

Find Deal

Sun, Jul 20 - Tue, Jul 29

5:05 pm - 11:50 amMDW-GCM

18h 45m2 stops

12:45 pm - 11:00 pmGCM-MDW

10h 15m2 stops

$576Southwest

Find Deal

Sun, Jul 20 - Tue, Jul 29

5:00 am - 11:50 amMDW-GCM

6h 50m1 stop

12:45 pm - 8:15 pmGCM-MDW

7h 30m1 stop

$582Southwest

Find Deal

Thu, Jul 17 - Sun, Jul 20

5:00 am - 11:50 amMDW-GCM

6h 50m1 stop

12:45 pm - 11:55 pmGCM-MDW

11h 10m2 stops

$606Southwest

Find Deal

Thu, Jul 17 - Sun, Jul 20

6:00 am - 11:25 amMDW-GCM

5h 25m1 stop

12:40 pm - 9:41 pmGCM-MDW

9h 01m1 stop

$610Delta

Find Deal

Mon, Jul 21 - Tue, Jul 29

8:00 pm - 11:50 amMDW-GCM

15h 50m2 stops

12:45 pm - 9:40 pmGCM-MDW

8h 55m2 stops

$620Southwest

Find Deal

Thu, Jun 19 - Wed, Jun 25

4:06 pm - 4:00 pmMDW-GCM

23h 54m1 stop

12:40 pm - 10:36 pmGCM-MDW

9h 56m1 stop

$626

Find Deal

Thu, Jul 17 - Sun, Jul 27

5:00 am - 11:50 amMDW-GCM

6h 50m1 stop

12:45 pm - 9:40 pmGCM-MDW

8h 55m2 stops

$630Southwest

Find Deal

Thu, Jun 19 - Wed, Jun 25

6:00 am - 11:25 amMDW-GCM

5h 25m1 stop

12:40 pm - 9:41 pmGCM-MDW

9h 01m1 stop

$635Delta

Find Deal

Thu, Jul 17 - Tue, Jul 29

6:00 am - 11:20 amMDW-GCM

5h 20m1 stop

12:40 pm - 9:45 pmGCM-MDW

9h 05m1 stop

$660Delta

Find Deal

Mon, Jun 2 - Mon, Jun 9

Useful Info

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.

Airlines

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to the Cayman Islands were found on Southwest ($542) and Delta ($610).

Find deals

Cheapest flight	$231

Flight from Chicago Midway Airport to George Town

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

Airports

Cabin class

Complete your trip

Flights to other cities

Origins

Popular routes

Return flight deals

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

$231 Find Cheap Flights from Chicago Midway Airport to Cayman Islands

KAYAK searches hundreds of travel sites at once for deals on flights to the Cayman Islands

Best Cayman Islands Flight Deals from Midway

Cheap Flight Deals from Midway to the Cayman Islands (MDW-KY0)

Recent round-trip flight deals from Midway to the Cayman Islands

Recent one-way flight deals from Midway to the Cayman Islands

Recent last minute flight deals from Midway to the Cayman Islands

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?

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to the Cayman Islands were found on Southwest ($542) and Delta ($610).

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 18m.

Good to know

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

Cabin class types available on flights to the Cayman Islands

Complete your trip to the Cayman Islands with a hotel stay or car rental

Flights to other popular destinations

Flights from domestic origins to the Cayman Islands

Flights to popular cities in the Cayman Islands

Find deals for your return flight