Find Cheap Flights from Chicago 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.
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Book cheap flights from Chicago to Cayman Islands

(Round-trip)
Depart: Mon Jan 15 2018 Return: Wed Jan 24 2018 Trip spans 10 days
Air Canada
Air Canada
ORD
GCM
16h 20m
1 stop
GCM
ORD
8h 57m
1 stop
Depart: Thu Dec 7 2017 Return: Mon Dec 11 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
ORD
GCM
10h 40m
1 stop
GCM
ORD
21h 19m
1 stop
Depart: Thu Nov 23 2017 Return: Sun Dec 3 2017 Trip spans 11 days
American Airlines
American Airlines
ORD
GCM
6h 11m
1 stop
GCM
ORD
11h 29m
1 stop
Depart: Sat Nov 11 2017 Return: Sat Nov 18 2017 Trip spans 8 days
United
United
ORD
GCM
3h 50m
nonstop
GCM
ORD
4h 00m
nonstop
Depart: Sat Jan 6 2018 Return: Sat Jan 13 2018 Trip spans 8 days
Delta
Delta
MDW
GCM
12h 04m
1 stop
GCM
MDW
6h 43m
1 stop
Depart: Tue Jan 16 2018 Return: Wed Jan 24 2018 Trip spans 9 days
Air Canada
Air Canada
ORD
GCM
16h 20m
1 stop
GCM
ORD
8h 57m
1 stop
Depart: Tue Nov 7 2017 Return: Tue Nov 14 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
ORD
GCM
10h 40m
1 stop
GCM
ORD
31h 23m
1 stop
Depart: Tue Jan 23 2018 Return: Tue Jan 30 2018 Trip spans 8 days
Air Canada
Air Canada
ORD
GCM
16h 20m
1 stop
GCM
ORD
8h 57m
1 stop
Depart: Fri Nov 24 2017 Return: Mon Dec 4 2017 Trip spans 11 days
American Airlines
American Airlines
ORD
GCM
14h 41m
1 stop
GCM
ORD
11h 29m
1 stop
Depart: Sat Nov 25 2017 Return: Sat Dec 2 2017 Trip spans 8 days
United
United
ORD
GCM
3h 50m
nonstop
GCM
ORD
4h 00m
nonstop
Depart: Sun Dec 10 2017 Return: Sun Dec 17 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
ORD
GCM
28h 35m
1 stop
GCM
ORD
45h 29m
1 stop
Depart: Sat Jan 13 2018 Return: Mon Jan 22 2018 Trip spans 10 days
Delta
Delta
MDW
GCM
12h 10m
1 stop
GCM
MDW
7h 23m
1 stop
Depart: Tue Mar 20 2018 Return: Wed Mar 28 2018 Trip spans 9 days
Air Canada
Air Canada
ORD
GCM
16h 20m
1 stop
GCM
ORD
9h 02m
1 stop
Depart: Sun Mar 4 2018 Return: Sun Mar 11 2018 Trip spans 8 days
United
United
ORD
GCM
3h 50m
nonstop
GCM
ORD
4h 05m
nonstop
Depart: Sun Jan 14 2018 Return: Sun Jan 21 2018 Trip spans 8 days
American Airlines
American Airlines
ORD
GCM
6h 27m
1 stop
GCM
ORD
9h 29m
1 stop
Depart: Sat Apr 7 2018 Return: Wed Apr 11 2018 Trip spans 5 days
Multiple Airlines
Multiple Airlines
ORD
GCM
16h 45m
1 stop
GCM
ORD
7h 32m
1 stop
Depart: Sat Feb 10 2018 Return: Sat Feb 17 2018 Trip spans 8 days
Delta
Delta
MDW
GCM
8h 20m
1 stop
GCM
MDW
6h 43m
1 stop
Depart: Mon Mar 26 2018 Return: Wed Mar 28 2018 Trip spans 3 days
Air Canada
Air Canada
ORD
GCM
16h 20m
1 stop
GCM
ORD
7h 22m
1 stop
Depart: Tue Nov 21 2017 Return: Sat Dec 2 2017 Trip spans 12 days
United
United
ORD
GCM
14h 40m
1 stop
GCM
ORD
4h 00m
nonstop
Depart: Tue Jan 16 2018 Return: Sun Jan 21 2018 Trip spans 6 days
American Airlines
American Airlines
ORD
GCM
6h 13m
1 stop
GCM
ORD
9h 29m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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
only $425
only $503
Destination

George Town
$425