Flight Routes from Chicago to Key West

Compare cheap outbound and return flights from Chicago (CHI) to Key West (EYW) and find the best offer from numerous airlines and travel agencies.

Trip type
Fastest flight
non-stop flights
6x / week
Flight distance
2,004 km
Time difference
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL

Flight schedule from Chicago (CHI) to Key West (EYW)

Select a travel date in the flight schedule for the route from Chicago (CHI) to Key West (EYW) and compare affordable flight deals.

offers
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Matching outbound flightsCHI–EYW · 2 of 2
fromto
dep.arr.
durationstopovers
  1. September 13 – 19, 2026
  2. September 20 – 26, 2026
  3. Sep 27 – Oct 3, 2026
    1. ORDEYW
      nonstop
      1. United Airlines
    2. ORDEYW
      nonstop
      1. United Airlines

      Important flight information

      Discover more flights around Chicago and Key West

      Departure airport Airport Chicago-IL, all airports (CHI)
      Arrival airport Airport Key West-FL (EYW)
      Destination country Flights to United States
      Departure airport - Destination country Chicago-IL, all airports - United States
      Alternative flights to Key West