Book United Chicago to Key West flight deals from $389

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Search flights from Chicago to Key West (ORD - EYW)

October

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Saturday 6th

Return Sunday 21st
from$ 446*Viewed: 3 hours ago

Tuesday 9th

Return Wednesday 24th
from$ 513*Viewed: 3 hours ago

Wednesday 10th

Return Thursday 25th
from$ 556*Viewed: 3 hours ago

November

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Monday 26th

Return Tuesday 11th
from$ 447*Viewed: 3 hours ago

Tuesday 27th

Return Wednesday 12th
from$ 447*Viewed: 3 hours ago

Wednesday 28th

Return Thursday 13th
from$ 442*Viewed: 3 hours ago

December

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Tuesday 4th

Return Wednesday 19th
from$ 389*Viewed: 3 hours ago

Friday 7th

Return Saturday 22nd
from$ 389*Viewed: 3 hours ago

Monday 10th

Return Tuesday 25th
from$ 442*Viewed: 3 hours ago
**Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply..
A dock leads into turquoise waters off a white sandy beach in Key West

Plan ahead for flights from Chicago to Key West

from
to
Type
Dates
Price*
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Tue 4 Dec 2018
Return Wed 19 Dec 2018
from$ 389*Viewed: 3 hours ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Fri 7 Dec 2018
Return Sat 22 Dec 2018
from$ 389*Viewed: 3 hours ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Thu 15 Aug 2019
Return Tue 20 Aug 2019
from$ 389*Viewed: 22 hours ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Wed 27 Mar 2019
Return Wed 3 Apr 2019
from$ 397*Viewed: 1 day ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Sat 29 Sep 2018
Return Sun 14 Oct 2018
from$ 442*Viewed: 3 hours ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Wed 28 Nov 2018
Return Thu 13 Dec 2018
from$ 442*Viewed: 3 hours ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Sun 2 Dec 2018
Return Mon 17 Dec 2018
from$ 442*Viewed: 3 hours ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Mon 3 Dec 2018
Return Tue 18 Dec 2018
from$ 442*Viewed: 3 hours ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Thu 6 Dec 2018
Return Fri 21 Dec 2018
from$ 442*Viewed: 3 hours ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Sun 9 Dec 2018
Return Mon 24 Dec 2018
from$ 442*Viewed: 3 hours ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.