Find Cheap Flights from Chicago Midway to Cayman Islands

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago Midway to Cayman Islands

(Round-trip)
Depart: Mon Dec 11 2017 Return: Fri Dec 22 2017 Trip spans 12 days
Delta
Delta
MDW
12:00a
GCM
6:42a
6h 42m
1 stop
GCM
12:00a
MDW
10:13a
10h 13m
1 stop
Depart: Sat Jan 6 2018 Return: Sat Jan 13 2018 Trip spans 8 days
Delta
Delta
MDW
12:00a
GCM
7:54a
7h 54m
1 stop
GCM
12:00a
MDW
6:43a
6h 43m
1 stop
Depart: Mon Jan 22 2018 Return: Tue Jan 30 2018 Trip spans 9 days
Delta
Delta
MDW
12:00a
GCM
6:35a
6h 35m
1 stop
GCM
12:00a
MDW
7:23a
7h 23m
1 stop
Depart: Thu Feb 1 2018 Return: Mon Feb 5 2018 Trip spans 5 days
Delta
Delta
MDW
12:00a
GCM
6:35a
6h 35m
1 stop
GCM
12:00a
MDW
7:23a
7h 23m
1 stop
Depart: Sat Mar 3 2018 Return: Wed Mar 14 2018 Trip spans 11 days
Delta
Delta
MDW
12:00a
GCM
8:20a
8h 20m
1 stop
GCM
12:00a
MDW
9:08a
9h 08m
1 stop
Depart: Wed Mar 7 2018 Return: Tue Mar 13 2018 Trip spans 6 days
Delta
Delta
MDW
12:00a
GCM
6:35a
6h 35m
1 stop
GCM
12:00a
MDW
7:02a
7h 02m
1 stop
Depart: Sat Dec 2 2017 Return: Sun Dec 10 2017 Trip spans 9 days
Delta
Delta
MDW
12:00a
GCM
6:02p
18h 02m
1 stop
GCM
12:00a
MDW
11:04a
11h 04m
1 stop
Depart: Thu Apr 5 2018 Return: Thu Apr 12 2018 Trip spans 8 days
Delta
Delta
MDW
12:00a
GCM
5:15a
5h 15m
1 stop
GCM
12:00a
MDW
9:08a
9h 08m
1 stop
Depart: Sun Apr 29 2018 Return: Sun May 6 2018 Trip spans 8 days
Delta
Delta
MDW
12:00a
GCM
5:15a
5h 15m
1 stop
GCM
12:00a
MDW
9:08a
9h 08m
1 stop
Depart: Sat Dec 30 2017 Return: Sat Jan 6 2018 Trip spans 8 days
Delta
Delta
MDW
12:00a
GCM
7:54a
7h 54m
1 stop
GCM
12:00a
MDW
10:18a
10h 18m
1 stop
Depart: Thu Apr 12 2018 Return: Sat Apr 21 2018 Trip spans 10 days
Delta
Delta
MDW
12:00a
GCM
6:35a
6h 35m
1 stop
GCM
12:00a
MDW
7:23a
7h 23m
1 stop
Depart: Sat Mar 24 2018 Return: Sat Mar 31 2018 Trip spans 8 days
Delta
Delta
MDW
12:00a
GCM
10:50a
10h 50m
1 stop
GCM
12:00a
MDW
6:05p
18h 05m
1 stop
Depart: Tue Nov 7 2017 Return: Tue Nov 14 2017 Trip spans 8 days
Delta
Delta
MDW
12:00a
GCM
6:38a
6h 38m
1 stop
GCM
12:00a
MDW
9:10a
9h 10m
1 stop
Depart: Sun Nov 26 2017 Return: Sat Dec 2 2017 Trip spans 7 days
$1365
Select
Delta
Delta
MDW
12:00a
GCM
5:23a
5h 23m
1 stop
GCM
12:00a
MDW
7:48a
7h 48m
1 stop
Depart: Wed Dec 27 2017 Return: Wed Jan 3 2018 Trip spans 8 days
$1490
Select
Delta
Delta
MDW
12:00a
GCM
4:52p
16h 52m
1 stop
GCM
12:00a
MDW
9:09a
9h 09m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Chicago
$503
Destination

George Town
$503
Airlines