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

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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 $209 and $98 for one-way flights to Key West for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Jul 2 - Thu, Jul 4
ORD
O'Hare Intl.
EYW
Key West Intl.
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 2 from O'Hare Intl. to Key West Intl., returning Thu, Jul 4, priced at $209 found 1 day ago
American Airlines
Thu, Aug 15 - Tue, Aug 20
ORD
O'Hare Intl.
EYW
Key West Intl.
$212 Roundtrip, found 4 days ago
$212
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Aug 15 from O'Hare Intl. to Key West Intl., returning Tue, Aug 20, priced at $212 found 4 days ago
Delta
Tue, Sep 24 - Tue, Oct 8
MDW
Midway Intl.
EYW
Key West Intl.
$216 Roundtrip, found 5 days ago
$216
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Sep 24 from Midway Intl. to Key West Intl., returning Tue, Oct 8, priced at $216 found 5 days ago

Save more with Key West Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (MDW) to Key West (EYW)
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Save 100% on your flight
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (MDW) to Key West (EYW)
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (MDW) to Key West (EYW)
Beachside Resort & Residences

Beachside Resort & Residences

4 out of 5
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (MDW) to Key West (EYW)
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (MDW) 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 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (MDW) to Key West (EYW)
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