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: Sun Jan 21 2018 Return: Sun Jan 28 2018 Trip spans 8 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Sat Dec 9 2017 Return: Sat Dec 16 2017 Trip spans 8 days
United
United
ORD
GCM
3h 50m
nonstop
GCM
ORD
15h 45m
1 stop
Depart: Fri Sep 22 2017 Return: Mon Oct 2 2017 Trip spans 11 days
American Airlines
American Airlines
ORD
GCM
6h 19m
1 stop
GCM
ORD
9h 24m
1 stop
Depart: Fri Sep 22 2017 Return: Mon Sep 25 2017 Trip spans 4 days
Delta
Delta
MDW
GCM
6h 38m
1 stop
GCM
MDW
7h 11m
1 stop
Depart: Sat Nov 11 2017 Return: Sat Nov 18 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
GCM
3h 50m
nonstop
GCM
ORD
4h 05m
nonstop
Depart: Sun Feb 11 2018 Return: Sun Feb 18 2018 Trip spans 8 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Sun Jan 21 2018 Return: Sun Jan 28 2018 Trip spans 8 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Thu Sep 28 2017 Return: Sun Oct 1 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
GCM
8h 04m
1 stop
GCM
ORD
9h 24m
1 stop
Depart: Fri Oct 13 2017 Return: Sun Oct 15 2017 Trip spans 3 days
Delta
Delta
MDW
GCM
5h 20m
1 stop
GCM
MDW
9h 00m
1 stop
Depart: Tue Jan 2 2018 Return: Sun Jan 7 2018 Trip spans 6 days
United
United
ORD
GCM
16h 45m
1 stop
GCM
ORD
26h 35m
1 stop
Depart: Wed Oct 11 2017 Return: Wed Oct 18 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
GCM
8h 11m
1 stop
GCM
ORD
9h 12m
1 stop
Depart: Sun Nov 5 2017 Return: Sat Nov 11 2017 Trip spans 7 days
Delta
Delta
MDW
GCM
6h 31m
1 stop
GCM
MDW
9h 17m
1 stop
Depart: Fri Oct 27 2017 Return: Mon Oct 30 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
GCM
6h 26m
1 stop
GCM
ORD
6h 23m
1 stop
Depart: Fri Dec 8 2017 Return: Thu Dec 14 2017 Trip spans 7 days
Delta
Delta
MDW
GCM
6h 31m
1 stop
GCM
MDW
7h 42m
1 stop
Depart: Sat Nov 4 2017 Return: Sat Nov 11 2017 Trip spans 8 days
United
United
ORD
GCM
3h 50m
nonstop
GCM
ORD
4h 05m
nonstop
Depart: Thu Feb 1 2018 Return: Thu Feb 8 2018 Trip spans 8 days
American Airlines
American Airlines
ORD
GCM
7h 53m
1 stop
GCM
ORD
6h 20m
1 stop
Depart: Sun Dec 17 2017 Return: Sun Dec 24 2017 Trip spans 8 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Sun Dec 10 2017 Return: Sat Dec 16 2017 Trip spans 7 days
Delta
Delta
MDW
GCM
6h 31m
1 stop
GCM
MDW
7h 42m
1 stop
Depart: Sat Dec 30 2017 Return: Sat Jan 6 2018 Trip spans 8 days
United
United
ORD
GCM
13h 50m
1 stop
GCM
ORD
18h 01m
1 stop
Depart: Thu Nov 2 2017 Return: Mon Nov 6 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
GCM
11h 24m
1 stop
GCM
ORD
9h 14m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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Airports
Origin

Chicago
only $429
only $503
Destination

George Town
$429