Find Cheap Flights from Chicago (CHI) to Key West (EYW) from

Many airlines offer flexible change policies

Earn BONUS+ rewardsOpens in a new window on top of your airline points

Enjoy exclusive promotions on the ebookers app!

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 23 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
Dieses Hotel für Familien bietet dir einen angenehmen Aufenthalt in Key West. Freu dich auf WLAN-Internetzugang (kostenlos), 2 Außenpools und 2 Restaurants. ...
8.2/10 Very Good! (2,044 reviews)
Beautiful and clean

Reviewed on 6 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
Dieses Hotel in Strandnähe bietet dir einen angenehmen Aufenthalt in Key West. Freu dich auf WLAN-Internetzugang (kostenlos), 3 Außenpools und Wellnessbereich. ...
8.8/10 Excellent! (3,177 reviews)
Never enough beach or pool chairs

Reviewed on 6 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
Dieses Hotel in Strandnähe bietet dir einen angenehmen Aufenthalt in Key West. Freu dich auf Frühstück (gegen Gebühr), Zimmerservice (bitte Zeiten beachten) ...
8.8/10 Excellent! (1,804 reviews)
Nice place that offered great accommodations!

Reviewed on 5 Apr 2026

Opens in a new windowMargaritaville Beach House Key West
Save an average of 15% on thousands of hotels when you're signed in
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Dieses Hotel in Strandnähe bietet dir einen angenehmen Aufenthalt in Key West. Freu dich auf WLAN-Internetzugang (kostenlos), 2 Restaurants und Privatstrand. ...
8.6/10 Excellent! (2,119 reviews)
Room floors were unswept and so was balcony. Balcony had an entire snack bar on the floor of balcony. I found a watch battery on the floor of the main bathroom. I was with my 13 month old baby. Had he found that and swallowed it we would have a bigger issue at hand. I went to front desk and ask that ...

Reviewed on 6 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
Dieses Hotel in Strandnähe bietet dir einen angenehmen Aufenthalt in Key West. Freu dich auf inbegriffenes Frühstück, WLAN-Internetzugang (kostenlos) und Privatstrand. ...
8/10 Very Good! (2,184 reviews)
Parking was easy

Reviewed on 5 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
Dieses Hotel für Geschäftsreisende bietet dir einen angenehmen Aufenthalt in Key West. Freu dich auf WLAN-Internetzugang (kostenlos), Parken ohne Service (kostenlos) ...
9/10 Wonderful! (1,727 reviews)
The property was friendly with pets. Staff very nice.

Reviewed on 6 Apr 2026

Opens in a new windowHavana Cabana at Key West
Don't see what you're looking for?
See all available properties in Key West
View all properties
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.

^Savings based on all holiday package bookings with Flight + Hotel made on ebookers.ie from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.