Cheap Flights from Chicago to Key West

View €188 flight on Mon, 12 May 2025Opens in a new window

Popular airlines from Chicago to Key West

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Cheap flights from Chicago to Key West (CHI-EYW)

Prices were available within the past 7 days and start at €188 for one-way flights and €231 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Mon, 12 May - Wed, 21 May
ORD
Chicago
EYW
Key West
€231 Return, found 14 hours ago
€231
Return
found 14 hours ago
Select American Airlines flight, departing Mon, 12 May from Chicago to Key West, returning Wed, 21 May, priced at €231 found 14 hours ago
American Airlines
Mon, 19 May - Wed, 28 May
ORD
Chicago
EYW
Key West
€232 Return, found 4 days ago
€232
Return
found 4 days ago
Select American Airlines flight, departing Mon, 19 May from Chicago to Key West, returning Wed, 28 May, priced at €232 found 4 days ago
Delta
Mon, 12 May - Wed, 21 May
MDW
Chicago
EYW
Key West
€249 Return, found 14 hours ago
€249
Return
found 14 hours ago
Select Delta flight, departing Mon, 12 May from Chicago to Key West, returning Wed, 21 May, priced at €249 found 14 hours ago
Delta
Mon, 12 May - Wed, 21 May
ORD
Chicago
EYW
Key West
€249 Return, found 14 hours ago
€249
Return
found 14 hours ago
Select Delta flight, departing Mon, 12 May from Chicago to Key West, returning Wed, 21 May, priced at €249 found 14 hours ago
American Airlines
Mon, 12 May - Wed, 21 May
ORD
Chicago
EYW
Key West
€258 Return, found 14 hours ago
€258
Return
found 14 hours ago
Select American Airlines flight, departing Mon, 12 May from Chicago to Key West, returning Wed, 21 May, priced at €258 found 14 hours ago
United
Mon, 12 May - Wed, 21 May
ORD
Chicago
EYW
Key West
€381 Return, found 14 hours ago
€381
Return
found 14 hours ago
Select United flight, departing Mon, 12 May from Chicago to Key West, returning Wed, 21 May, priced at €381 found 14 hours ago
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