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Cheap Flights from Chicago to Key West & Flight Information
Origin airport IATA code
CHI
Destination airport IATA code
EYW
Number of flight options
1
Average flight time
4 hours 25 mins

Key West Flight Information

Traveling From
Chicago
Origin Airport IATA Code
CHI
Traveling To
Key West
Destination Airport IATA Code
EYW
Number of Airlines Serving
Available Airlines
Distance
Direct Flight Time
Flight Price

Need a car after flight from Chicago to Key West

Place to stay after flight from Chicago to Key West

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Yövy tässä perheille sopivassa hotellissa kohteessa Key West. Nauti ilmaisesta Wi-Fi-yhteydestä, 2 ulkouima-altaasta ja 2 ravintolasta. Asiakkaamme kehuvat majoituspaikan ...
8.2/10 Very Good! (2,039 reviews)
Clean room, friendly staff and grounds around the property are kept up.

Reviewed on 5 Apr 2026

Opens in a new windowBlue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Yövy tässä rannalla sijaitsevassa hotellissa kohteessa Key West. Nauti ilmaisesta Wi-Fi-yhteydestä, 3 ulkouima-altaasta ja täyden palvelun kylpylästä. Asiakkaamme ...
8.8/10 Excellent! (3,170 reviews)
Wonderful beach views, clean rooms and property, great food

Reviewed on 5 Apr 2026

Opens in a new windowSouthernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Yövy tässä rannalla sijaitsevassa hotellissa kohteessa Key West. Nauti aamiaisesta (lisämaksusta), huonepalvelusta ja ympäri vuorokauden auki olevasta kuntokeskuksesta. ...
8.8/10 Excellent! (1,800 reviews)
Ideal for families with smaller children, and the pool was smaller than was indicated in the pictures overall good experience

Reviewed on 2 Apr 2026

Opens in a new windowMargaritaville Beach House Key West
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Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Yövy tässä rannalla sijaitsevassa hotellissa kohteessa Key West. Nauti ilmaisesta Wi-Fi-yhteydestä, 2 ravintolasta ja yksityisestä rannasta. Asiakkaamme kehuvat ...
8.6/10 Excellent! (2,115 reviews)
When I arrived, they issued, the wrong rooms, then I informed them these aren't the display on Expedia site, they informed me, the mistake was false advertisement on you guys site, but as personal favor to me, they would the one seen on Expedia, but would've wait several hours, before they were cleaned, ...

Reviewed on 4 Apr 2026

Opens in a new windowBeachside Resort & Residences
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Yövy tässä rannalla sijaitsevassa hotellissa kohteessa Key West. Nauti ilmaisesta aamiaisesta, ilmaisesta Wi-Fi-yhteydestä ja yksityisestä rannasta. Asiakkaamme ...
8/10 Very Good! (2,182 reviews)
This is an older resort but clean. I would not recommend you eat at the restaurant it’s not that great.

Reviewed on 4 Apr 2026

Opens in a new windowIbis Bay Beach Resort
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Yövy tässä liikematkustukseen soveltuvassa hotellissa kohteessa Key West. Nauti ilmaisesta Wi-Fi-yhteydestä, ilmaisesta pysäköinnistä ja aamiaisesta (lisämaksusta). ...
9/10 Wonderful! (1,723 reviews)
Pool perfect. Hot tub private. Drinks and breakfast very good. Through Expedia they offered free breakfast for everyday we stayed. Came around with free Jell-O shots, smoothies and snacks. Flama Cabana bar was nice with good music, dinner was ok. Espresso Martinis on point! Beautiful sunset from ...

Reviewed on 4 Apr 2026

Opens in a new windowHavana Cabana at Key West
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Flight prices above are per person all prepaid taxes and online service fees included and subject to availability