Find Deals on 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
Students
under 26
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 to Cayman Islands

(Round-trip)
Depart: Mon Jan 30 2017 Return: Sat Feb 4 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
GCM
17h 23m
1 stop
GCM
ORD
8h 06m
1 stop
Depart: Sun Feb 5 2017 Return: Thu Feb 9 2017 Trip spans 5 days
JetBlue
JetBlue
ORD
GCM
17h 23m
1 stop
GCM
ORD
29h 03m
1 stop
Depart: Sat Feb 11 2017 Return: Sat Feb 18 2017 Trip spans 8 days
United
United
ORD
GCM
3h 50m
nonstop
GCM
ORD
4h 05m
nonstop
Depart: Wed Jan 11 2017 Return: Wed Jan 18 2017 Trip spans 8 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 50m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Sun Feb 19 2017 Return: Thu Mar 2 2017 Trip spans 12 days
American Airlines
American Airlines
ORD
GCM
6h 08m
1 stop
GCM
ORD
6h 27m
1 stop
Depart: Sat Dec 31 2016 Return: Fri Jan 6 2017 Trip spans 7 days
Delta
Delta
MDW
GCM
6h 43m
1 stop
GCM
MDW
7h 53m
1 stop
Depart: Sat Jun 3 2017 Return: Sat Jun 10 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
GCM
19h 04m
1 stop
GCM
ORD
18h 20m
1 stop
Depart: Sat Apr 29 2017 Return: Sat May 6 2017 Trip spans 8 days
United
United
ORD
GCM
3h 55m
nonstop
GCM
ORD
4h 10m
nonstop
Depart: Wed Jun 28 2017 Return: Tue Jul 4 2017 Trip spans 7 days
American Airlines
American Airlines
ORD
GCM
7h 53m
1 stop
GCM
ORD
9h 17m
1 stop
Depart: Wed Jan 4 2017 Return: Sun Jan 15 2017 Trip spans 12 days
Delta
Delta
MDW
GCM
13h 35m
1 stop
GCM
MDW
8h 27m
1 stop
Depart: Mon Dec 19 2016 Return: Mon Jan 30 2017 Trip spans 43 days
Major Airline
Major Airline
ORD
GCM
18h 35m
1 stop
GCM
ORD
8h 47m
1 stop
Depart: Sat May 6 2017 Return: Sat May 13 2017 Trip spans 8 days
United
United
ORD
GCM
3h 55m
nonstop
GCM
ORD
4h 10m
nonstop
Depart: Wed Apr 26 2017 Return: Sun Apr 30 2017 Trip spans 5 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
4h 00m
nonstop
Depart: Wed May 17 2017 Return: Sun May 21 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
GCM
5h 50m
1 stop
GCM
ORD
7h 30m
1 stop
Depart: Mon Jan 9 2017 Return: Sun Feb 5 2017 Trip spans 28 days
Delta
Delta
MDW
GCM
6h 43m
1 stop
GCM
MDW
8h 27m
1 stop
Depart: Sun Mar 5 2017 Return: Sun Mar 12 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
GCM
3h 50m
nonstop
GCM
ORD
4h 05m
nonstop
Depart: Sat May 6 2017 Return: Sat May 13 2017 Trip spans 8 days
United
United
ORD
GCM
3h 55m
nonstop
GCM
ORD
4h 10m
nonstop
Depart: Sun Feb 19 2017 Return: Thu Mar 2 2017 Trip spans 12 days
Delta
Delta
MDW
GCM
5h 26m
1 stop
GCM
MDW
6h 34m
1 stop
Depart: Mon Mar 27 2017 Return: Mon Apr 3 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
GCM
19h 30m
1 stop
GCM
ORD
25h 00m
1 stop
Depart: Sun Feb 26 2017 Return: Mon Mar 6 2017 Trip spans 9 days
Delta
Delta
MDW
GCM
6h 31m
1 stop
GCM
MDW
8h 38m
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
only $423
only $491
Destination

George Town
$423