Cheap flights from Chicago to Raccoon Key

View AU$403 flight on Sun, 31 Aug. 2025Opens in a new window

Popular airlines from Chicago to Raccoon Key

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Cheap Flights from Chicago (CHI) to Raccoon Key (EYW)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Wed, 6 May - Sun, 10 May
ORD
Chicago
EYW
Key West
AU$509 Return, found 3 days ago
AU$509
Return
found 3 days ago
Select United flight, departing Wed, 6 May from Chicago to Key West, returning Sun, 10 May, priced at AU$509 found 3 days ago
American Airlines
Sun, 31 Aug. - Sun, 7 Sep.
ORD
Chicago
EYW
Key West
AU$565 Return, found 6 days ago
AU$565
Return
found 6 days ago
Select American Airlines flight, departing Sun, 31 Aug. from Chicago to Key West, returning Sun, 7 Sep., priced at AU$565 found 6 days ago
American Airlines
Sun, 31 Aug. - Sun, 7 Sep.
ORD
Chicago
EYW
Key West
AU$597 Return, found 6 days ago
AU$597
Return
found 6 days ago
Select American Airlines flight, departing Sun, 31 Aug. from Chicago to Key West, returning Sun, 7 Sep., priced at AU$597 found 6 days ago
United
Wed, 6 May - Sun, 10 May
ORD
Chicago
EYW
Key West
AU$632 Return, found 3 days ago
AU$632
Return
found 3 days ago
Select United flight, departing Wed, 6 May from Chicago to Key West, returning Sun, 10 May, priced at AU$632 found 3 days ago
American Airlines
Sun, 31 Aug. - Sun, 7 Sep.
ORD
Chicago
EYW
Key West
AU$672 Return, found 6 days ago
AU$672
Return
found 6 days ago
Select American Airlines flight, departing Sun, 31 Aug. from Chicago to Key West, returning Sun, 7 Sep., priced at AU$672 found 6 days ago
Delta
Sun, 31 Aug. - Sun, 7 Sep.
MDW
Chicago
EYW
Key West
AU$1,398 Return, found 6 days ago
AU$1,398
Return
found 6 days ago
Select Delta flight, departing Sun, 31 Aug. from Chicago to Key West, returning Sun, 7 Sep., priced at AU$1,398 found 6 days ago

Find the cheapest month to fly from Chicago (CHI) to Key West (EYW)

November is typically the cheapest month to fly

From AU$290 - AU$993 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.