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: Thu Sep 14 2017 Return: Sun Sep 17 2017 Trip spans 4 days
JetBlue
JetBlue
ORD
GCM
16h 10m
1 stop
GCM
ORD
18h 17m
1 stop
Depart: Sun Jul 30 2017 Return: Sun Aug 6 2017 Trip spans 8 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Sat Aug 5 2017 Return: Sat Aug 12 2017 Trip spans 8 days
United
United
ORD
GCM
3h 55m
nonstop
GCM
ORD
4h 10m
nonstop
Depart: Fri Nov 3 2017 Return: Sat Nov 11 2017 Trip spans 9 days
Multiple Airlines
Multiple Airlines
ORD
GCM
7h 53m
1 stop
GCM
ORD
4h 05m
nonstop
Depart: Sat Aug 26 2017 Return: Sun Sep 3 2017 Trip spans 9 days
American Airlines
American Airlines
ORD
GCM
8h 04m
1 stop
GCM
ORD
9h 24m
1 stop
Depart: Tue Jul 18 2017 Return: Thu Jul 27 2017 Trip spans 10 days
Delta
Delta
MDW
GCM
6h 41m
1 stop
GCM
MDW
7h 23m
1 stop
Depart: Sat Jul 8 2017 Return: Sat Jul 15 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
GCM
16h 34m
nonstop
GCM
ORD
18h 53m
nonstop
Depart: Sat Dec 9 2017 Return: Sat Dec 16 2017 Trip spans 8 days
United
United
ORD
GCM
3h 50m
nonstop
GCM
ORD
4h 05m
nonstop
Depart: Thu Oct 12 2017 Return: Mon Oct 16 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
GCM
7h 53m
1 stop
GCM
ORD
9h 17m
1 stop
Depart: Wed Aug 30 2017 Return: Sat Sep 2 2017 Trip spans 4 days
Delta
Delta
MDW
GCM
6h 31m
1 stop
GCM
MDW
7h 06m
1 stop
Depart: Sun Dec 10 2017 Return: Sat Dec 16 2017 Trip spans 7 days
United
United
ORD
GCM
6h 10m
1 stop
GCM
ORD
4h 05m
nonstop
Depart: Mon Sep 25 2017 Return: Sat Sep 30 2017 Trip spans 6 days
Delta
Delta
MDW
GCM
5h 11m
1 stop
GCM
MDW
7h 30m
1 stop
Depart: Sat Jul 8 2017 Return: Sat Jul 15 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
GCM
16h 34m
nonstop
GCM
ORD
18h 53m
nonstop
Depart: Sat Nov 4 2017 Return: Sun Nov 12 2017 Trip spans 9 days
Delta
Delta
MDW
GCM
5h 31m
1 stop
GCM
MDW
13h 54m
1 stop
Depart: Sun Dec 24 2017 Return: Sun Dec 31 2017 Trip spans 8 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Thu Dec 7 2017 Return: Mon Dec 11 2017 Trip spans 5 days
Delta
Delta
MDW
GCM
5h 11m
1 stop
GCM
MDW
6h 55m
1 stop
Depart: Sat Dec 23 2017 Return: Sat Dec 30 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
GCM
24h 24m
nonstop
GCM
ORD
29h 59m
nonstop
Depart: Fri Jun 30 2017 Return: Tue Jul 4 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
ORD
GCM
16h 28m
1 stop
GCM
ORD
23h 37m
1 stop
Depart: Sun Dec 10 2017 Return: Sat Dec 16 2017 Trip spans 7 days
Delta
Delta
MDW
GCM
6h 31m
1 stop
GCM
MDW
6h 53m
1 stop
Depart: Fri Jun 30 2017 Return: Tue Jul 4 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
GCM
13h 00m
1 stop
GCM
ORD
9h 06m
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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^ The fares displayed in KAYAK ads found on other sites include all taxes and fees for economy class travel and were found by KAYAK users in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.
Airports
Origin

Chicago
only $459
only $503
Destination

George Town
$459