Book United Chicago to Key West flight deals from $383

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

August

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Saturday 4th

Return Sunday 19th
from$ 387*Viewed: 24 minutes ago

Saturday 18th

Return Sunday 2nd
from$ 441*Viewed: 24 minutes ago

Friday 24th

Return Saturday 8th
from$ 441*Viewed: 24 minutes ago

September

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Saturday 22nd

Return Sunday 7th
from$ 421*Viewed: 24 minutes ago

Friday 28th

Return Saturday 13th
from$ 441*Viewed: 24 minutes ago

Saturday 29th

Return Sunday 14th
from$ 421*Viewed: 24 minutes ago

October

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Saturday 6th

Return Sunday 21st
from$ 421*Viewed: 24 minutes ago

Monday 8th

Return Tuesday 23rd
from$ 450*Viewed: 24 minutes ago

Wednesday 17th

Return Thursday 1st
from$ 450*Viewed: 24 minutes 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 Sun 2 Jun 2019
Return Fri 7 Jun 2019
from$ 383*Viewed: 1 day ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Sat 4 Aug 2018
Return Sun 19 Aug 2018
from$ 387*Viewed: 24 minutes ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Sat 28 Jul 2018
Return Sun 12 Aug 2018
from$ 421*Viewed: 24 minutes ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Sat 22 Sep 2018
Return Sun 7 Oct 2018
from$ 421*Viewed: 24 minutes ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Sat 29 Sep 2018
Return Sun 14 Oct 2018
from$ 421*Viewed: 24 minutes ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Sat 6 Oct 2018
Return Sun 21 Oct 2018
from$ 421*Viewed: 24 minutes ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Sat 18 Aug 2018
Return Sun 2 Sep 2018
from$ 441*Viewed: 24 minutes ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Fri 24 Aug 2018
Return Sat 8 Sep 2018
from$ 441*Viewed: 24 minutes ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Fri 7 Sep 2018
Return Sat 22 Sep 2018
from$ 441*Viewed: 24 minutes ago
Chicago (ORD)
to Key West (EYW)
Roundtrip
Depart Fri 14 Sep 2018
Return Sat 29 Sep 2018
from$ 441*Viewed: 24 minutes 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.

Weather in Key West

86 °FFriday07/20/2018
86 °FSaturday07/21/2018
86 °FSunday07/22/2018
85 °FMonday07/23/2018
86 °FTuesday07/24/2018
86 °FWednesday07/25/2018
85 °FThursday07/26/2018
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