Chicago to Key West Flights (CHI-EYW) from $98

Selected fares from Chicago to Key West

The cheapest prices found with in the last 7 days for return flights were $198 and $98 for one-way flights to Key West for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Sep 14 - Sat, Sep 21

ORD

O'Hare Intl.

EYW

Key West Intl.

$198 Roundtrip, found 3 days ago

$198

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sat, Sep 14 from O'Hare Intl. to Key West Intl., returning Sat, Sep 21, priced at $198 found 3 days ago

Tue, Sep 10 - Sat, Sep 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$210 Roundtrip, found 22 hours ago

$210

Roundtrip

found 22 hours ago

Select American Airlines flight, departing Tue, Sep 10 from O'Hare Intl. to Key West Intl., returning Sat, Sep 14, priced at $210 found 22 hours ago

Tue, Aug 27 - Tue, Sep 10

MDW

Midway Intl.

EYW

Key West Intl.

$216 Roundtrip, found 6 days ago

$216

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Aug 27 from Midway Intl. to Key West Intl., returning Tue, Sep 10, priced at $216 found 6 days ago