Chicago to Key West Flights (CHI-EYW) from $99

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Selected fares from Chicago to Key West

The cheapest prices found with in the last 7 days for return flights were $215 and $99 for one-way flights to Key West for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, Jul 16 - Tue, Jul 23
ORD
O'Hare Intl.
EYW
Key West Intl.
$215 Roundtrip, found 2 days ago
$215
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jul 16 from O'Hare Intl. to Key West Intl., returning Tue, Jul 23, priced at $215 found 2 days ago
Delta
Sat, Aug 24 - Tue, Sep 10
MDW
Midway Intl.
EYW
Key West Intl.
$216 Roundtrip, found 3 days ago
$216
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Aug 24 from Midway Intl. to Key West Intl., returning Tue, Sep 10, priced at $216 found 3 days ago
Delta
Tue, Aug 13 - Sat, Aug 31
ORD
O'Hare Intl.
EYW
Key West Intl.
$216 Roundtrip, found 12 hours ago
$216
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, Aug 13 from O'Hare Intl. to Key West Intl., returning Sat, Aug 31, priced at $216 found 12 hours ago

Save more with Key West Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

5 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 29
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 29
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Beachside Resort & Residences

Beachside Resort & Residences

4 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 29
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 29
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 29
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Save 100% on your flight
per person
Jun 25 - Jun 29
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
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