Cheap flights from Midway (MDW) to Grand Cayman

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

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

All the information you need to plan the best MDW to GCM flight in 2022: compare Midway to Grand Cayman flight prices with the expected peak season, weather and rainfall in Grand Cayman.
What is the cheapest month to fly from Chicago Midway Airport to Grand Cayman?

The best pricing can be found in the month of April. Prices to Grand Cayman from Chicago Midway Airport average $644. You can even find prices in April for less than $644, as users have found deals to Grand Cayman from as low as $474. The month of December appears to be one of the more expensive times to travel to Grand Cayman from Chicago Midway Airport. Flying in the targeted month can save you up to 39%.

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

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 Grand Cayman as you normally would.

How far in advance should I book a flight from Chicago Midway Airport to Grand Cayman?

To save up to 48% on this flight, we recommend booking at least 61 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago Midway Airport to Grand Cayman from $849 1-2 weeks out and tickets from $990 for flights departing within the next 72 hours.

Cheap flights from Midway to Grand Cayman in June, July 2022

The best prices found for MDW to Grand Cayman flights for June, July
26 Jul - 4 Aug
$621pp
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
9 Jul - 16 Jul
$743pp
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Delta
 
1 STOP
MDW
Chicago Midway
26 Jul - 4 Aug
$746pp
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 Grand Cayman 2022 flight deals

Cheap flights to Grand Cayman from Midway found for this year
21 Aug - 25 Aug
$599pp
MDW
Chicago Midway
Delta
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Delta
 
1 STOP
MDW
Chicago Midway
19 Sep - 23 Sep
$604pp
MDW
Chicago Midway
Delta
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Delta
   
2 STOPS
MDW
Chicago Midway
13 Aug - 20 Aug
$611pp
MDW
Chicago Midway
Multiple Airlines
   
2 STOPS
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Multiple Airlines
 
1 STOP
MDW
Chicago Midway

Last minute flights from Midway to Grand Cayman

Late deals on round-trip flights to Grand Cayman from Midway, departing today and this week
9 Jul - 16 Jul
$743pp
MDW
Chicago Midway
Multiple Airlines
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Delta
 
1 STOP
MDW
Chicago Midway
9 Jul - 16 Jul
$799pp
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
9 Jul - 16 Jul
$899pp
MDW
Chicago Midway
Delta
 
1 STOP
GCM
George Town Owen Roberts Intl
GCM
George Town Owen Roberts Intl
Delta
 
1 STOP
MDW
Chicago Midway

One-way flights to Grand Cayman from Chicago Midway

The cheapest one-way flights from Midway to Grand Cayman
1:00 am - 7:25 am
Delta
1 Stop
5h 25m
MDW - GCM
Delta
$450
Delta
7:05 am - 11:40 am
Multiple Airlines
1 Stop
27h 35m
MDW - GCM
Multiple Airlines
$607
Kiwi.com
1:00 am - 7:25 am
Delta
1 Stop
5h 25m
MDW - GCM
Delta
$1,321
Delta

Related info for your journey

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

Flight FAQs

From Midway to Grand Cayman

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

Yes, there are multiple flights from Chicago Midway Airport to Grand Cayman for under $600. The cheapest flight booked recently is on Delta for just $599, but on average you can expect to pay $694.

Are there last-minute flights available from Chicago Midway Airport to Grand Cayman for under $800?

There are currently 5+ open flights from Chicago Midway Airport to Grand Cayman within the next 7 days for less than $800.

Related searches

Flights to Grand Cayman from Midway
Flights to Midway Flights to Grand Cayman Flights from Midway

Rent a Car

Car Rentals at George Town

COVID Restrictions

View COVID Travel Restrictions for Grand Cayman

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

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

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

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 Grand Cayman.

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

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

Returning to Chicago Midway from Grand Cayman

COVID-19 testing requirements
Visitors from Grand Cayman are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago Midway.

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

Hide COVID Travel Restrictions for Grand Cayman

Destination information for Grand Cayman

Things to know before you go - useful duration and weather info for your trip from Midway to Grand Cayman.
Today's exchange rate
$1 = $0.84
Average temperature for June in Grand Cayman
89.6 °F
Avg rainfall for June in Grand Cayman
5.4 ″

Airports servicing Chicago

Airports servicing

George Town Owen Roberts Intl (GCM)
Home Caribbean Cayman Islands Grand Cayman Cheap flights from Midway to Grand Cayman