Cheap flights from Midway (MDW) to Cayman Islands

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How to find the cheapest flight from
Midway (MDW) to Cayman Islands

All the information you need to plan the best MDW to GCM flight in 2022: compare Midway to Cayman Islands flight prices with the expected peak season, weather and rainfall in Cayman Islands.
How far in advance should I book a flight from Chicago Midway Airport to Cayman Islands?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 26 days in advance, which can save you up to 3% on flights from Chicago Midway Airport to Cayman Islands compared to booking the week you need them. Waiting 26 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $470. For sooner than that we have options available in the next 3 days from $485.

What is the cheapest month to fly from Chicago Midway Airport to Cayman Islands?

Flights from Chicago Midway Airport to Cayman Islands lean towards being more expensive in December. Prices are generally better when you fly from Chicago Midway Airport to Cayman Islands in September, with the cheapest ticket starting at $362.

When is the cheapest time to fly from Chicago Midway Airport to Cayman Islands (MDW - KY)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Cayman Islands as you normally would.

Cheap flights from Midway to Cayman Islands in May, June 2022

The best prices found for MDW to Cayman Islands flights for May, June
22 Jun - 27 Jun
$610pp
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
18 Jun - 26 Jun
$622pp
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway
18 Jun - 24 Jun
$639pp
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Multiple Airlines
   
2 STOPS
MDW
Chicago Midway

Chicago Midway to Cayman Islands 2022 flight deals

Cheap flights to Cayman Islands from Midway found for this year
12 Sep - 19 Sep
$579pp
MDW
Chicago Midway
Delta
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Delta
 
1 STOP
MDW
Chicago Midway
12 Sep - 19 Sep
$584pp
MDW
Chicago Midway
Delta
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Delta
   
2 STOPS
MDW
Chicago Midway
10 Dec - 17 Dec
$604pp
MDW
Chicago Midway
Delta
   
2 STOPS
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Delta
 
1 STOP
MDW
Chicago Midway

Last minute flights from Midway to Cayman Islands

Late deals on round-trip flights to Cayman Islands from Midway, departing today and this week
2 Jun - 6 Jun
$1,106pp
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Delta
 
1 STOP
MDW
Chicago Midway
2 Jun - 6 Jun
$1,132pp
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Delta
 
1 STOP
MDW
Chicago Midway
2 Jun - 6 Jun
$1,404pp
MDW
Chicago Midway
Delta
   
2 STOPS
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Delta
   
2 STOPS
MDW
Chicago Midway

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Midway</span> to <span class="emphasized">Cayman Islands</span> flights.

Flight FAQs

From Midway to Cayman Islands

Can I find flights from Chicago Midway Airport to Cayman Islands for under $600 on Cheapflights?

Yes, there are multiple flights from Chicago Midway Airport to Cayman Islands for under $600. The cheapest flight booked recently is on Delta for just $579, but on average you can expect to pay $661.

Are there last-minute flights available from Chicago Midway Airport to Cayman Islands for under $1,200?

There are currently 3+ open flights from Chicago Midway Airport to Cayman Islands within the next 7 days for less than $1,200.

Related searches

Flights to Cayman Islands from Midway
Flights to Midway Flights to Cayman Islands Flights from Midway

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COVID Restrictions

View COVID Travel Restrictions for Cayman Islands

Do I need a COVID test to fly to Cayman Islands from Midway?

Information is based on travel restrictions from Chicago Midway to Cayman Islands

Most visitors from Chicago Midway need to provide a negative COVID-19 test result and/or quarantine to enter Cayman Islands.

COVID-19 testing requirements
Visitors from Chicago Midway must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) before departing to Cayman Islands.

Quarantine requirements
Visitors from Chicago Midway are not required to quarantine after entering Cayman Islands.

Do I need a test to fly back to Midway from Cayman Islands?

Returning to Chicago Midway from Cayman Islands

COVID-19 testing requirements
Visitors from Cayman Islands must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) before departing to Chicago Midway.

Quarantine requirements
Visitors from Cayman Islands are not required to quarantine after entering Chicago Midway.

Hide COVID Travel Restrictions for Cayman Islands

Destination information for Cayman Islands

Things to know before you go - useful duration and weather info for your trip from Midway to Cayman Islands.
Today's exchange rate
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Airports servicing Chicago

Airports servicing

Cayman Brac Gerrard-Smith (CYB)
George Town Owen Roberts Intl (GCM)
Little Cayman (LYB)
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