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
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago to Cayman Islands

(Round-trip)
Depart: Wed Sep 20 2017 Return: Mon Sep 25 2017 Trip spans 6 days
Delta
Delta
MDW
GCM
17h 11m
1 stop
GCM
MDW
9h 18m
1 stop
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
3h 55m
nonstop
Depart: Fri May 12 2017 Return: Tue May 16 2017 Trip spans 5 days
Major Airline
Major Airline
MDW
GCM
3h 11m
1 stop
GCM
MDW
3h 11m
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: Sun Jun 4 2017 Return: Sat Jun 10 2017 Trip spans 7 days
American Airlines
American Airlines
ORD
GCM
8h 11m
1 stop
GCM
ORD
11h 17m
1 stop
Depart: Fri Apr 28 2017 Return: Tue May 2 2017 Trip spans 5 days
Delta
Delta
MDW
GCM
5h 17m
1 stop
GCM
MDW
8h 45m
1 stop
Depart: Tue Apr 25 2017 Return: Sat Apr 29 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
GCM
7h 35m
1 stop
GCM
ORD
7h 41m
1 stop
Depart: Sun Jul 16 2017 Return: Sun Jul 23 2017 Trip spans 8 days
Cayman Airways
Cayman Airways
ORD
GCM
3h 55m
nonstop
GCM
ORD
3h 55m
nonstop
Depart: Sat May 20 2017 Return: Sat May 27 2017 Trip spans 8 days
United
United
ORD
GCM
3h 55m
nonstop
GCM
ORD
4h 10m
nonstop
Depart: Thu Jul 6 2017 Return: Thu Jul 13 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
GCM
7h 53m
1 stop
GCM
ORD
9h 17m
1 stop
Depart: Wed Sep 20 2017 Return: Mon Sep 25 2017 Trip spans 6 days
Delta
Delta
ORD
GCM
15h 41m
2 stops
GCM
ORD
18h 02m
2 stops
Depart: Sat Aug 12 2017 Return: Sat Aug 19 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
GCM
15h 36m
2 stops
GCM
ORD
18h 53m
2 stops
Depart: Sat Jun 17 2017 Return: Tue Jun 27 2017 Trip spans 11 days
United
United
ORD
GCM
3h 55m
nonstop
GCM
ORD
15h 11m
1 stop
Depart: Mon Aug 7 2017 Return: Fri Aug 11 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
GCM
5h 50m
1 stop
GCM
ORD
6h 20m
1 stop
Depart: Sun May 7 2017 Return: Sat May 13 2017 Trip spans 7 days
Delta
Delta
MDW
GCM
17h 15m
1 stop
GCM
MDW
8h 44m
1 stop
Depart: Sat Jun 10 2017 Return: Sat Jun 17 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
GCM
16h 43m
1 stop
GCM
ORD
14h 13m
1 stop
Depart: Thu Jun 8 2017 Return: Sat Jun 17 2017 Trip spans 10 days
Major Airline
Major Airline
ORD
GCM
13h 50m
1 stop
GCM
ORD
7h 22m
1 stop
Depart: Sun Aug 27 2017 Return: Sun Sep 3 2017 Trip spans 8 days
Delta
Delta
MDW
GCM
5h 11m
1 stop
GCM
MDW
9h 18m
1 stop
Depart: Sun Apr 2 2017 Return: Sun Apr 9 2017 Trip spans 8 days
United
United
ORD
GCM
3h 50m
nonstop
GCM
ORD
7h 57m
1 stop
Depart: Thu Aug 31 2017 Return: Mon Sep 4 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
GCM
27h 31m
2 stops
GCM
ORD
18h 53m
2 stops
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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 $439
only $409
Destination

George Town
$409