Find Deals on Flights from Cayman Islands to Chicago

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 Cayman Islands to Chicago

(Round-trip)
Depart: Sat Apr 1 2017 Return: Sun Apr 16 2017 Trip spans 16 days
Major Airline
Major Airline
GCM
ORD
27h 24m
nonstop
ORD
GCM
18h 54m
nonstop
Depart: Thu May 4 2017 Return: Sun May 7 2017 Trip spans 4 days
Delta
Delta
GCM
ORD
8h 35m
1 stop
ORD
GCM
5h 16m
1 stop
Depart: Sat Apr 8 2017 Return: Fri Apr 14 2017 Trip spans 7 days
American Airlines
American Airlines
GCM
ORD
18h 24m
1 stop
ORD
GCM
16h 46m
1 stop
Depart: Fri Mar 31 2017 Return: Sun Apr 16 2017 Trip spans 17 days
United
United
GCM
ORD
40h 45m
2 stops
ORD
GCM
3h 55m
nonstop
Depart: Thu May 4 2017 Return: Sun May 7 2017 Trip spans 4 days
Delta
Delta
GCM
MDW
8h 34m
1 stop
MDW
GCM
5h 26m
1 stop
Depart: Fri Apr 14 2017 Return: Mon Apr 17 2017 Trip spans 4 days
American Airlines
American Airlines
GCM
ORD
18h 40m
1 stop
ORD
GCM
16h 30m
1 stop
Depart: Mon Apr 3 2017 Return: Fri Apr 14 2017 Trip spans 12 days
Delta
Delta
GCM
MDW
22h 11m
1 stop
MDW
GCM
25h 37m
2 stops
Depart: Fri Apr 14 2017 Return: Mon Apr 17 2017 Trip spans 4 days
Delta
Delta
GCM
MDW
30h 57m
2 stops
MDW
GCM
20h 45m
1 stop
Depart: Sat Apr 8 2017 Return: Fri Apr 14 2017 Trip spans 7 days
$2329
Select
Delta
Delta
GCM
MDW
7h 30m
1 stop
MDW
GCM
16h 51m
2 stops
* 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

George Town
$441
Destination

Chicago
only $441
only $488