Find Deals on Flights from Chicago O'Hare International 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 O'Hare International to Cayman Islands

(Round-trip)
Depart: Wed May 24 2017 Return: Fri Jun 2 2017 Trip spans 10 days
JetBlue
JetBlue
ORD
4:35p
GCM
8:38a
16h 03m
1 stop
GCM
9:34a
ORD
3:53p
30h 19m
1 stop
Depart: Fri May 26 2017 Return: Thu Jun 1 2017 Trip spans 7 days
Major Airline
Major Airline
ORD
12:35p
GCM
4:38a
16h 03m
2 stops
GCM
5:34a
ORD
3:04a
21h 30m
2 stops
Depart: Sat Jan 28 2017 Return: Sat Feb 4 2017 Trip spans 8 days
United
United
ORD
5:40a
GCM
9:30a
3h 50m
nonstop
GCM
7:39a
ORD
11:44a
4h 05m
nonstop
Depart: Wed Jan 4 2017 Return: Thu Jan 12 2017 Trip spans 9 days
American Airlines
American Airlines
ORD
12:30a
GCM
8:27a
7h 57m
1 stop
GCM
10:35a
ORD
5:06p
6h 31m
1 stop
Depart: Sun Jan 1 2017 Return: Fri Jan 6 2017 Trip spans 6 days
Delta
Delta
ORD
6:21a
GCM
2:40p
8h 19m
1 stop
GCM
3:00a
ORD
10:54a
7h 54m
1 stop
Depart: Fri Mar 24 2017 Return: Fri Mar 31 2017 Trip spans 8 days
Air Canada
Air Canada
ORD
3:40p
GCM
8:35a
16h 55m
1 stop
GCM
8:50a
ORD
8:35a
23h 45m
1 stop
Depart: Thu May 4 2017 Return: Mon May 8 2017 Trip spans 5 days
JetBlue
JetBlue
ORD
4:35p
GCM
8:38a
16h 03m
1 stop
GCM
9:34a
ORD
3:54a
18h 20m
1 stop
Depart: Thu May 25 2017 Return: Fri Jun 2 2017 Trip spans 9 days
JetBlue
JetBlue
ORD
4:35p
GCM
8:38a
16h 03m
1 stop
GCM
9:34a
ORD
3:53p
30h 19m
1 stop
Depart: Tue Jan 24 2017 Return: Sat Jan 28 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
7:31a
GCM
2:10a
18h 39m
2 stops
GCM
4:15a
ORD
11:15p
19h 00m
2 stops
Depart: Sat Feb 11 2017 Return: Sat Feb 18 2017 Trip spans 8 days
United
United
ORD
5:40a
GCM
9:30a
3h 50m
nonstop
GCM
7:40a
ORD
11:45a
4h 05m
nonstop
Depart: Thu Jan 5 2017 Return: Sat Jan 14 2017 Trip spans 10 days
American Airlines
American Airlines
ORD
2:15a
GCM
8:27a
6h 12m
1 stop
GCM
8:47a
ORD
5:06p
8h 19m
1 stop
Depart: Wed Feb 1 2017 Return: Sun Feb 5 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
7:59a
GCM
1:22a
17h 23m
1 stop
GCM
3:19a
ORD
8:22a
29h 03m
1 stop
Depart: Sat Mar 4 2017 Return: Sat Mar 11 2017 Trip spans 8 days
United
United
ORD
5:40a
GCM
9:30a
3h 50m
nonstop
GCM
7:36a
ORD
11:41a
4h 05m
nonstop
Depart: Wed Dec 21 2016 Return: Mon Dec 26 2016 Trip spans 6 days
Delta
Delta
ORD
11:45a
GCM
2:39p
26h 54m
1 stop
GCM
3:00a
ORD
7:49p
16h 49m
1 stop
Depart: Tue Jan 10 2017 Return: Sat Jan 14 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
2:15a
GCM
8:33a
6h 18m
1 stop
GCM
10:35a
ORD
7:47p
9h 12m
1 stop
Depart: Mon Jan 9 2017 Return: Fri Jan 13 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
7:35a
GCM
2:10a
18h 35m
1 stop
GCM
4:00a
ORD
8:00a
28h 00m
1 stop
Depart: Sun Jun 11 2017 Return: Fri Jun 16 2017 Trip spans 6 days
JetBlue
JetBlue
ORD
4:35a
GCM
8:38a
28h 03m
1 stop
GCM
9:13a
ORD
6:49a
21h 36m
1 stop
Depart: Sat May 6 2017 Return: Sat May 13 2017 Trip spans 8 days
United
United
ORD
6:40a
GCM
10:35a
3h 55m
nonstop
GCM
7:45a
ORD
11:55a
4h 10m
nonstop
Depart: Thu Jan 12 2017 Return: Fri Jan 20 2017 Trip spans 9 days
American Airlines
American Airlines
ORD
2:15a
GCM
8:33a
6h 18m
1 stop
GCM
10:35a
ORD
5:06p
6h 31m
1 stop
Depart: Fri Jan 13 2017 Return: Tue Jan 17 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
8:00p
GCM
2:35a
6h 35m
1 stop
GCM
3:50a
ORD
12:37p
8h 47m
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.

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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,
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Airports
Origin

Chicago
$363
Destination

George Town
$363