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From Chicago
Current:
Chicago to Key West
Chicago ✈ Key West
Cheapest airfares from Chicago to Key West
Search for flight deals to Key West
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All prices in AUD, prices may fluctuate slightly from the advertised price.
Fly on Wed, Feb 25th 2026
From
$241
Frontier Airlines
F9 3044 (1 Transfer)
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Fly on Wed, May 6th 2026
From
$255
Frontier Airlines
F9 2205 (2 Transfers)
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Fly on Mon, Oct 19th 2026
From
$316
United Airlines
UA 3595 (Direct)
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Fly on Fri, Mar 27th 2026
From
$466
Spirit Airlines
NK 570 (1 Transfer)
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