Chicago to Key West Flights (CHI-EYW) from $108

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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 $216 and $108 for one-way flights to Key West for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, Sep 1 - Wed, Sep 4
ORD
O'Hare Intl.
EYW
Key West Intl.
$216 Roundtrip, found 5 days ago
$216
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Sep 1 from O'Hare Intl. to Key West Intl., returning Wed, Sep 4, priced at $216 found 5 days ago
Delta
Tue, Nov 12 - Wed, Nov 20
MDW
Midway Intl.
EYW
Key West Intl.
$248 Roundtrip, found 20 hours ago
$248
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Nov 12 from Midway Intl. to Key West Intl., returning Wed, Nov 20, priced at $248 found 20 hours ago
United
Tue, Dec 17 - Tue, Mar 11
ORD
O'Hare Intl.
EYW
Key West Intl.
$268 Roundtrip, found 6 days ago
$268
Roundtrip
found 6 days ago
Select United flight, departing Tue, Dec 17 from O'Hare Intl. to Key West Intl., returning Tue, Mar 11, priced at $268 found 6 days ago

Save more with Key West Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Gates Hotel Key West

The Gates Hotel Key West

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
Havana Cabana at Key West - Adults Only

Havana Cabana at Key West - Adults Only

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jul 7 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Key West (EYW)
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jul 7 - Jul 12
found 1 day ago
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
Jul 4 - Jul 8
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Key West (EYW)
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