Find Cheap 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: Mon Aug 28 2017 Return: Tue Aug 29 2017 Trip spans 2 days
American Airlines
American Airlines
GCM
ORD
6h 20m
1 stop
ORD
GCM
10h 31m
2 stops
Depart: Sun Jul 30 2017 Return: Sun Aug 13 2017 Trip spans 15 days
Cayman Airways
Cayman Airways
GCM
ORD
3h 55m
nonstop
ORD
GCM
3h 55m
nonstop
Depart: Fri Aug 25 2017 Return: Mon Aug 28 2017 Trip spans 4 days
Delta
Delta
GCM
MDW
9h 18m
1 stop
MDW
GCM
17h 11m
1 stop
Depart: Fri May 19 2017 Return: Mon May 22 2017 Trip spans 4 days
American Airlines
American Airlines
GCM
ORD
8h 55m
1 stop
ORD
GCM
8h 14m
1 stop
Depart: Fri May 19 2017 Return: Mon May 22 2017 Trip spans 4 days
Delta
Delta
GCM
MDW
8h 45m
1 stop
MDW
GCM
5h 15m
1 stop
Depart: Mon Jul 31 2017 Return: Sun Aug 13 2017 Trip spans 14 days
Delta
Delta
GCM
MDW
25h 47m
1 stop
MDW
GCM
23h 21m
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.

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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

George Town
$445
Destination

Chicago
only $445
only $488
Airlines Airline reviews

1 traveler who booked a flight from George Town to Chicago rated their chosen airline with an average of 6.6

Overall
8.0
Boarding
10.0
Crew
8.0
Comfort
4.0
Food
8.0
Entertainment
2.0