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

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 Grand Cayman. 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 Grand Cayman?

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

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 Grand Cayman 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 Grand Cayman?

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 Grand Cayman 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>

Which airlines provide the cheapest flights from Chicago Midway Airport to Grand Cayman?

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to Grand Cayman were found on Delta ($545) and Southwest ($606).

What is the cheapest time of day to fly to Grand Cayman?

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

$208 CHEAP FLIGHTS from Chicago Midway to Grand Cayman

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Flights Deals

One-wayRound-trip

George Town1 stop$545

Cheap Flights from Midway to Grand Cayman

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

Round-trip

One-way

Last minute

Recent round-trip flight deals from Midway to Grand Cayman

Sun, Oct 12 - Sun, Oct 19

6:00 am - 11:42 amMDW-GCM

5h 42m1 stop

1:02 pm - 9:44 pmGCM-MDW

8h 42m1 stop

$545Delta

Find Deal

Sun, Aug 24 - Thu, Aug 28

6:04 am - 11:37 amMDW-GCM

5h 33m1 stop

12:50 pm - 9:49 pmGCM-MDW

8h 59m1 stop

$570Delta

Find Deal

Sat, Aug 30 - Thu, Sep 4

6:00 am - 11:37 amMDW-GCM

5h 37m1 stop

12:50 pm - 9:26 pmGCM-MDW

8h 36m1 stop

$595Delta

Find Deal

Fri, Jul 25 - Fri, Aug 1

9:45 pm - 10:35 amMDW-GCM

12h 50m1 stop

12:45 pm - 7:45 pmGCM-MDW

7h 00m1 stop

$606Southwest

Find Deal

Fri, Jul 25 - Fri, Aug 1

9:45 pm - 10:35 amMDW-GCM

12h 50m1 stop

12:45 pm - 1:05 amGCM-MDW

12h 20m2 stops

$610Southwest

Find Deal

Fri, Aug 22 - Sun, Aug 31

6:04 am - 11:37 amMDW-GCM

5h 33m1 stop

12:52 pm - 9:12 pmGCM-MDW

8h 20m1 stop

$620Delta

Find Deal

Fri, Jul 25 - Fri, Aug 1

9:45 pm - 12:10 pmMDW-GCM

14h 25m2 stops

12:45 pm - 1:05 amGCM-MDW

12h 20m2 stops

$650Southwest

Find Deal

Fri, Aug 22 - Sat, Aug 30

12:43 pm - 12:45 pmMDW-GCM

24h 02m2 stops

1:45 pm - 9:12 pmGCM-MDW

31h 27m2 stops

$3,360WestJet

Find Deal

Thu, Jul 3 - Tue, Jul 8

7:21 pm - 12:45 pmMDW-GCM

41h 24m2 stops

1:45 pm - 9:42 pmGCM-MDW

31h 57m2 stops

$3,377WestJet

Find Deal

Sun, Aug 24 - Sat, Aug 30

7:17 pm - 12:45 pmMDW-GCM

41h 28m2 stops

1:45 pm - 9:12 pmGCM-MDW

31h 27m2 stops

$3,385WestJet

Find Deal

Useful Info

KAYAK's insights & trends for Midway to Grand Cayman flights

Get data-powered insights and trends into flights from Midway to Grand Cayman to help you find the cheapest flights, the best time to fly and much more.

Prices

Airlines

Can I save money by flying with a layover from Chicago Midway Airport to Grand Cayman?

No, with an average price for the route of $341, prices are generally cheapest when you fly direct.

Find deals

Cheapest flight	$208

Flight from Chicago Midway Airport to George Town

How does KAYAK find such low prices on flights from Chicago Midway Airport to Grand Cayman?
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 Grand Cayman.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Grand Cayman?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Grand Cayman 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 Grand Cayman?
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 Grand Cayman 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 Grand Cayman?
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 Grand Cayman 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 Grand Cayman?
The cheapest time of day to fly to Grand Cayman is generally in the morning, when round-trip flights cost $615 on average. The most expensive time of day to fly to Grand Cayman 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 to Grand Cayman

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)

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$208 Find Cheap Flights from Chicago Midway Airport to Grand Cayman

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

Best Grand Cayman Flight Deals from Midway

Cheap Flights from Midway to Grand Cayman

Recent round-trip flight deals from Midway to Grand Cayman

Recent one-way flight deals from Midway to Grand Cayman

Recent last minute flight deals from Midway to Grand Cayman

KAYAK's insights & trends for Midway to Grand Cayman flights

Get data-powered insights and trends into flights from Midway to Grand Cayman to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Chicago Midway Airport to Grand Cayman?

No, with an average price for the route of $341, prices are generally cheapest when you fly direct.

Which airlines provide the cheapest flights from Chicago Midway Airport to Grand Cayman?

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to Grand Cayman were found on Delta ($545) and Southwest ($606).

Good to know

FAQs - booking Grand Cayman flights

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

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 Grand Cayman.

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

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

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 Grand Cayman 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 Grand Cayman?

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 Grand Cayman 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 Grand Cayman?

The cheapest time of day to fly to Grand Cayman is generally in the morning, when round-trip flights cost $615 on average. The most expensive time of day to fly to Grand Cayman 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 to Grand Cayman

Information on your arrival and departure airports

Cabin class types available on flights to Midway

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

Flights to other popular destinations

Flights from domestic origins to Midway

Flights to popular cities in Grand Cayman

Find deals for your return flight