Find Cheap Flights from Chicago to Key West (CHI - EYW)

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 Key West

(Round-trip)
Depart: Tue Oct 31 2017 Return: Tue Nov 7 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
ORD
EYW
7h 03m
1 stop
EYW
ORD
6h 13m
1 stop
Depart: Tue Oct 31 2017 Return: Tue Nov 7 2017 Trip spans 8 days
Delta
Delta
MDW
EYW
4h 35m
1 stop
EYW
MDW
7h 25m
1 stop
Depart: Thu Jan 4 2018 Return: Mon Jan 8 2018 Trip spans 5 days
United
United
ORD
EYW
7h 16m
1 stop
EYW
ORD
9h 25m
2 stops
Depart: Tue Sep 26 2017 Return: Tue Oct 3 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
EYW
8h 58m
1 stop
EYW
ORD
9h 14m
1 stop
Depart: Sun Nov 12 2017 Return: Wed Nov 15 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
ORD
EYW
7h 03m
1 stop
EYW
ORD
6h 13m
1 stop
Depart: Mon Nov 6 2017 Return: Thu Nov 9 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
ORD
EYW
7h 34m
1 stop
EYW
ORD
7h 03m
1 stop
Depart: Wed Dec 6 2017 Return: Wed Dec 13 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
ORD
EYW
7h 53m
1 stop
EYW
ORD
7h 41m
1 stop
Depart: Wed Dec 6 2017 Return: Wed Dec 13 2017 Trip spans 8 days
Delta
Delta
MDW
EYW
6h 50m
1 stop
EYW
MDW
5h 20m
1 stop
Depart: Tue Oct 17 2017 Return: Mon Oct 23 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
ORD
EYW
7h 18m
1 stop
EYW
ORD
11h 34m
1 stop
Depart: Sat Oct 14 2017 Return: Fri Oct 20 2017 Trip spans 7 days
Delta
Delta
MDW
EYW
4h 30m
1 stop
EYW
MDW
7h 20m
1 stop
Depart: Tue Oct 17 2017 Return: Mon Oct 23 2017 Trip spans 7 days
Delta
Delta
MDW
EYW
6h 30m
1 stop
EYW
MDW
6h 31m
1 stop
Depart: Sat Dec 16 2017 Return: Sat Dec 23 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
ORD
EYW
7h 04m
1 stop
EYW
ORD
18h 12m
1 stop
Depart: Wed Sep 27 2017 Return: Thu Oct 5 2017 Trip spans 9 days
JetBlue
JetBlue
ORD
EYW
7h 18m
1 stop
EYW
ORD
6h 01m
1 stop
Depart: Sun Nov 12 2017 Return: Wed Nov 15 2017 Trip spans 4 days
Delta
Delta
MDW
EYW
4h 31m
1 stop
EYW
MDW
6h 26m
1 stop
Depart: Fri Nov 10 2017 Return: Tue Nov 14 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
ORD
EYW
7h 03m
1 stop
EYW
ORD
6h 13m
1 stop
Depart: Wed Sep 27 2017 Return: Sun Oct 1 2017 Trip spans 5 days
JetBlue
JetBlue
ORD
EYW
7h 18m
1 stop
EYW
ORD
9h 14m
1 stop
Depart: Wed Dec 13 2017 Return: Sun Dec 17 2017 Trip spans 5 days
Delta
Delta
MDW
EYW
6h 50m
1 stop
EYW
MDW
6h 56m
1 stop
Depart: Thu Nov 2 2017 Return: Sun Nov 5 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
ORD
EYW
9h 28m
1 stop
EYW
ORD
9h 47m
1 stop
Depart: Wed Jan 24 2018 Return: Mon Jan 29 2018 Trip spans 6 days
Delta
Delta
ORD
EYW
7h 43m
1 stop
EYW
ORD
5h 17m
1 stop
Depart: Tue Dec 19 2017 Return: Sat Dec 23 2017 Trip spans 5 days
JetBlue
JetBlue
ORD
EYW
9h 23m
1 stop
EYW
ORD
6h 21m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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 $176
only $342
Destination

Key West
$176