Find Deals on 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
Students
under 26
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Chicago Midway to Cayman Islands

(Round-trip)
Depart: Tue Mar 21 2017 Return: Tue Apr 4 2017 Trip spans 15 days
Delta
Delta
MDW
2:00a
GCM
8:40a
6h 40m
1 stop
GCM
9:35a
MDW
4:02p
6h 27m
1 stop
Depart: Tue Mar 28 2017 Return: Tue Apr 4 2017 Trip spans 8 days
Delta
Delta
MDW
2:00a
GCM
8:40a
6h 40m
1 stop
GCM
9:35a
MDW
4:02p
6h 27m
1 stop
Depart: Wed Mar 29 2017 Return: Tue Apr 11 2017 Trip spans 14 days
Delta
Delta
MDW
2:00a
GCM
8:40a
6h 40m
1 stop
GCM
9:35a
MDW
4:02p
6h 27m
1 stop
Depart: Mon Apr 3 2017 Return: Tue Apr 11 2017 Trip spans 9 days
Delta
Delta
MDW
2:00a
GCM
8:31a
6h 31m
1 stop
GCM
9:35a
MDW
4:02p
6h 27m
1 stop
Depart: Wed Apr 19 2017 Return: Thu Apr 27 2017 Trip spans 9 days
Delta
Delta
MDW
2:00a
GCM
8:31a
6h 31m
1 stop
GCM
9:35a
MDW
4:02p
6h 27m
1 stop
Depart: Thu Apr 20 2017 Return: Thu Apr 27 2017 Trip spans 8 days
Delta
Delta
MDW
3:05a
GCM
8:31a
5h 26m
1 stop
GCM
9:35a
MDW
4:02p
6h 27m
1 stop
Depart: Fri Apr 21 2017 Return: Thu Apr 27 2017 Trip spans 7 days
Delta
Delta
MDW
2:00a
GCM
8:31a
6h 31m
1 stop
GCM
9:35a
MDW
4:02p
6h 27m
1 stop
Depart: Sat Apr 22 2017 Return: Thu Apr 27 2017 Trip spans 6 days
Delta
Delta
MDW
2:00a
GCM
8:31a
6h 31m
1 stop
GCM
9:35a
MDW
4:02p
6h 27m
1 stop
Depart: Sun Apr 23 2017 Return: Thu Apr 27 2017 Trip spans 5 days
Delta
Delta
MDW
2:00a
GCM
8:31a
6h 31m
1 stop
GCM
9:35a
MDW
4:02p
6h 27m
1 stop
Depart: Mon Apr 24 2017 Return: Thu Apr 27 2017 Trip spans 4 days
Delta
Delta
MDW
3:05a
GCM
8:31a
5h 26m
1 stop
GCM
9:35a
MDW
4:02p
6h 27m
1 stop
Depart: Tue Apr 25 2017 Return: Thu Apr 27 2017 Trip spans 3 days
Delta
Delta
MDW
2:00a
GCM
8:31a
6h 31m
1 stop
GCM
9:35a
MDW
4:02p
6h 27m
1 stop
Depart: Fri May 5 2017 Return: Tue May 9 2017 Trip spans 5 days
Delta
Delta
MDW
3:05a
GCM
8:31a
5h 26m
1 stop
GCM
9:35a
MDW
6:09p
8h 34m
1 stop
Depart: Sat May 6 2017 Return: Tue May 9 2017 Trip spans 4 days
Delta
Delta
MDW
3:05a
GCM
10:14a
7h 09m
1 stop
GCM
9:35a
MDW
6:09p
8h 34m
1 stop
Depart: Sun May 14 2017 Return: Thu May 18 2017 Trip spans 5 days
Delta
Delta
MDW
3:05a
GCM
8:31a
5h 26m
1 stop
GCM
9:35a
MDW
6:09p
8h 34m
1 stop
Depart: Mon May 15 2017 Return: Thu May 18 2017 Trip spans 4 days
Delta
Delta
MDW
2:00a
GCM
8:31a
6h 31m
1 stop
GCM
9:35a
MDW
6:09p
8h 34m
1 stop
Depart: Tue May 16 2017 Return: Thu May 18 2017 Trip spans 3 days
Delta
Delta
MDW
3:05a
GCM
8:31a
5h 26m
1 stop
GCM
9:35a
MDW
6:09p
8h 34m
1 stop
Depart: Wed May 17 2017 Return: Thu May 18 2017 Trip spans 2 days
Delta
Delta
MDW
3:05a
GCM
8:31a
5h 26m
1 stop
GCM
9:35a
MDW
4:01p
6h 26m
1 stop
Depart: Fri May 19 2017 Return: Sat May 20 2017 Trip spans 2 days
Delta
Delta
MDW
3:05a
GCM
8:31a
5h 26m
1 stop
GCM
11:14a
MDW
6:08p
6h 54m
1 stop
Depart: Sun May 21 2017 Return: Tue May 23 2017 Trip spans 3 days
Delta
Delta
MDW
3:05a
GCM
8:31a
5h 26m
1 stop
GCM
9:35a
MDW
6:09p
8h 34m
1 stop
Depart: Tue May 23 2017 Return: Wed May 24 2017 Trip spans 2 days
Delta
Delta
MDW
2:00a
GCM
8:31a
6h 31m
1 stop
GCM
9:35a
MDW
6:09p
8h 34m
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
$497
Destination

George Town
$497
Airlines