Book United Key West to Chicago flight deals from $389

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

October

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Saturday 6th

Return Sunday 21st
from$ 393*Viewed: 9 hours ago

Friday 12th

Return Saturday 27th
from$ 397*Viewed: 9 hours ago

Saturday 13th

Return Sunday 28th
from$ 389*Viewed: 9 hours ago

November

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Wednesday 28th

Return Thursday 13th
from$ 389*Viewed: 9 hours ago

Thursday 29th

Return Friday 14th
from$ 442*Viewed: 9 hours ago

Friday 30th

Return Saturday 15th
from$ 389*Viewed: 9 hours ago

December

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Saturday 1st

Return Sunday 16th
from$ 442*Viewed: 9 hours ago

Tuesday 4th

Return Wednesday 19th
from$ 442*Viewed: 9 hours ago

Saturday 15th

Return Sunday 30th
from$ 447*Viewed: 9 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..
Cruise ships and tour boats docked by a ferris wheel and urban buildings at Navy Pier in Chicago

Plan ahead for flights from Key West to Chicago

from
to
Type
Dates
Price*
Key West (EYW)
to Chicago (ORD)
Roundtrip
Depart Sat 13 Oct 2018
Return Sun 28 Oct 2018
from$ 389*Viewed: 9 hours ago
Key West (EYW)
to Chicago (ORD)
Roundtrip
Depart Wed 28 Nov 2018
Return Thu 13 Dec 2018
from$ 389*Viewed: 9 hours ago
Key West (EYW)
to Chicago (ORD)
Roundtrip
Depart Fri 30 Nov 2018
Return Sat 15 Dec 2018
from$ 389*Viewed: 9 hours ago
Key West (EYW)
to Chicago (ORD)
Roundtrip
Depart Sat 6 Oct 2018
Return Sun 21 Oct 2018
from$ 393*Viewed: 9 hours ago
Key West (EYW)
to Chicago (ORD)
Roundtrip
Depart Fri 12 Oct 2018
Return Sat 27 Oct 2018
from$ 397*Viewed: 9 hours ago
Key West (EYW)
to Chicago (ORD)
Roundtrip
Depart Sat 29 Sep 2018
Return Sun 14 Oct 2018
from$ 442*Viewed: 9 hours ago
Key West (EYW)
to Chicago (ORD)
Roundtrip
Depart Sat 27 Oct 2018
Return Sun 11 Nov 2018
from$ 442*Viewed: 9 hours ago
Key West (EYW)
to Chicago (ORD)
Roundtrip
Depart Thu 29 Nov 2018
Return Fri 14 Dec 2018
from$ 442*Viewed: 9 hours ago
Key West (EYW)
to Chicago (ORD)
Roundtrip
Depart Sat 1 Dec 2018
Return Sun 16 Dec 2018
from$ 442*Viewed: 9 hours ago
Key West (EYW)
to Chicago (ORD)
Roundtrip
Depart Tue 4 Dec 2018
Return Wed 19 Dec 2018
from$ 442*Viewed: 9 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.