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: Thu Jun 1 2017 Return: Tue Jun 6 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
EYW
6h 51m
1 stop
EYW
ORD
13h 13m
1 stop
Depart: Wed Oct 18 2017 Return: Wed Oct 25 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
EYW
7h 22m
1 stop
EYW
ORD
6h 58m
1 stop
Depart: Mon May 15 2017 Return: Tue May 16 2017 Trip spans 2 days
Delta
Delta
MDW
EYW
5h 50m
1 stop
EYW
MDW
5h 29m
1 stop
Depart: Sun Apr 30 2017 Return: Thu May 11 2017 Trip spans 12 days
JetBlue
JetBlue
ORD
EYW
8h 33m
1 stop
EYW
ORD
5h 23m
1 stop
Depart: Thu May 18 2017 Return: Mon May 22 2017 Trip spans 5 days
United
United
ORD
EYW
27h 46m
1 stop
EYW
ORD
22h 04m
1 stop
Depart: Thu Jun 15 2017 Return: Mon Jun 19 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
EYW
4h 51m
1 stop
EYW
ORD
14h 49m
1 stop
Depart: Sat May 27 2017 Return: Tue May 30 2017 Trip spans 4 days
Delta
Delta
MDW
EYW
5h 44m
1 stop
EYW
MDW
6h 05m
1 stop
Depart: Fri Jun 2 2017 Return: Tue Jun 6 2017 Trip spans 5 days
Delta
Delta
MDW
EYW
5h 45m
1 stop
EYW
MDW
5h 34m
1 stop
Depart: Wed Aug 2 2017 Return: Wed Aug 9 2017 Trip spans 8 days
Delta
Delta
MDW
EYW
6h 50m
1 stop
EYW
MDW
4h 45m
1 stop
Depart: Sun Aug 27 2017 Return: Thu Aug 31 2017 Trip spans 5 days
Delta
Delta
MDW
EYW
4h 45m
1 stop
EYW
MDW
5h 20m
1 stop
Depart: Fri May 5 2017 Return: Sun May 7 2017 Trip spans 3 days
Major Airline
Major Airline
ORD
EYW
1h 30m
nonstop
EYW
ORD
3h 30m
nonstop
Depart: Tue Sep 12 2017 Return: Tue Sep 19 2017 Trip spans 8 days
Delta
Delta
MDW
EYW
4h 45m
1 stop
EYW
MDW
6h 12m
1 stop
Depart: Mon Sep 25 2017 Return: Thu Sep 28 2017 Trip spans 4 days
Delta
Delta
MDW
EYW
7h 00m
1 stop
EYW
MDW
5h 20m
1 stop
Depart: Fri Apr 28 2017 Return: Sun Apr 30 2017 Trip spans 3 days
United
United
ORD
EYW
18h 28m
1 stop
EYW
ORD
6h 43m
1 stop
Depart: Wed Oct 11 2017 Return: Sat Oct 21 2017 Trip spans 11 days
Delta
Delta
MDW
EYW
6h 05m
1 stop
EYW
MDW
6h 01m
1 stop
Depart: Wed Oct 18 2017 Return: Fri Oct 20 2017 Trip spans 3 days
Delta
Delta
MDW
EYW
7h 25m
1 stop
EYW
MDW
6h 03m
1 stop
Depart: Wed Jul 12 2017 Return: Mon Jul 17 2017 Trip spans 6 days
Delta
Delta
MDW
EYW
6h 06m
1 stop
EYW
MDW
4h 45m
1 stop
Depart: Sat May 27 2017 Return: Thu Jun 1 2017 Trip spans 6 days
Delta
Delta
MDW
EYW
5h 44m
1 stop
EYW
MDW
4h 40m
1 stop
Depart: Thu Jun 15 2017 Return: Mon Jun 19 2017 Trip spans 5 days
Delta
Delta
MDW
EYW
6h 03m
1 stop
EYW
MDW
5h 15m
1 stop
Depart: Sat Jul 1 2017 Return: Sun Jul 9 2017 Trip spans 9 days
Delta
Delta
MDW
EYW
7h 23m
1 stop
EYW
MDW
6h 48m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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

Chicago
only $347
only $508
Destination

Key West
$347