Nonstop flights from Chicago to Key West
American Airlines flies this route daily, starting again Nov 1.
ORDChicago O'Hare International
1,255 mi · 7 flights a week
EYWKey West International
When they leave
Chicago time11:59a11:59aDeparts 11:59 AM
One departure, at 11:59 AM. It runs daily.
Every flight
Earliest first
Schedules last checked Sep 22, 2026. Times are local.
Flying from Chicago to Key West
American Airlines is the only airline flying nonstop from Chicago to Key West, daily on the Embraer 170.
The flight covers 1,255 miles.
Flying back, Key West to Chicago has 7 nonstop flights a week.
Return flights
More from Chicago
Find the cheapest day to fly from Chicago to Key West.
Schedules as of Oct 9, 2026.