Flights from Chicago to Key West from $ 408* or from $/mo

Changed bag rules and optional services         Cruise Packages

Featured daily fares for flights from Chicago (ORD) to Key West (EYW)

Try alternate month or interact with individual days below in order to find offers.
May 2025
No result for this month
Jun 2025
From$ 1,579*
Viewed: 11 hours ago
RoundTrip|Economy
Jul 2025
From$ 1,331*
Viewed: 11 hours ago
RoundTrip|Economy
$ 1.1K
Displaying fares for May-2025
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Range$ 1,143-$ 1,579

*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, 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. Schedules are subject to change without notice.