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Cheap Flights from Chicago to Key West (CHI-EYW)
Prices were available within the past 7 days and start at $95 for one-way flights and $189 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Nov 19 - Wed, Nov 20
ORD
Chicago
EYW
Key West
$189 Roundtrip, just found
$189
Roundtrip
just found
Mon, Nov 18 - Tue, Nov 19
ORD
Chicago
EYW
Key West
$209 Roundtrip, just found
$209
Roundtrip
just found
Tue, Dec 17 - Wed, Dec 18
MDW
Chicago
EYW
Key West
$218 Roundtrip, found 3 days ago
$218
Roundtrip
found 3 days ago
Sun, Dec 8 - Wed, Dec 18
ORD
Chicago
EYW
Key West
$219 Roundtrip, found 5 hours ago
$219
Roundtrip
found 5 hours ago
Tue, Dec 10 - Wed, Dec 11
ORD
Chicago
EYW
Key West
$229 Roundtrip, just found
$229
Roundtrip
just found
Tue, Jan 21 - Thu, Jan 30
MDW
Chicago
EYW
Key West
$243 Roundtrip, found 4 days ago
$243
Roundtrip
found 4 days ago
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*Available to One Key members.