Chicago (ORD) to Key West (EYW) flights
2 airlines fly nonstop from Chicago (ORD) to Key West (EYW): American Airlines and United Airlines. The two airports are 1,255 miles (2,019 km) apart. American Airlines is in oneworld and United Airlines is in Star Alliance. There are also 20 ways to fly it with one stop, through Atlanta, Tampa and Indianapolis and more.
Airlines flying nonstop from ORD to EYW
- American Airlinesoneworld · bookable with 9 programsWho books it
- United AirlinesStar Alliance · bookable with 13 programsWho books it
Book ORD to EYW with points
Loyalty programs that can book at least one of the nonstop airlines, from the Award Booking Guide.
- Air Canada AeroplanBooks United Airlines
- Air New Zealand AirpointsBooks United Airlines
- Alaska Atmos RewardsBooks American Airlines
- American AAdvantageBooks American Airlines
- ANA Mileage ClubBooks United Airlines
- Avianca LifeMilesBooks United Airlines
- British Airways ClubBooks American Airlines
- Cathay Pacific Asia MilesBooks American Airlines
- Emirates SkywardsBooks United Airlines
- EVA Air Infinity MileageLandsBooks United Airlines
- Finnair PlusBooks American Airlines
- Iberia ClubBooks American Airlines
- JAL Mileage BankBooks American Airlines
- JetBlue TrueBlueBooks United Airlines
- Lufthansa Miles & MoreBooks United Airlines
- Qantas Frequent FlyerBooks American Airlines
- Qatar Airways Privilege ClubBooks American Airlines
- Singapore Airlines KrisFlyerBooks United Airlines
- TAP Miles&GoBooks United Airlines
- Thai Royal Orchid PlusBooks United Airlines
- Turkish Airlines Miles&SmilesBooks United Airlines
- United MileagePlusBooks United Airlines
ORD to EYW with one stop
20 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Atlanta (ATL)Delta Air Lines the whole way
+1 - Via Tampa (TPA)American Airlines, Frontier Airlines and 1 more, then Breeze Airways
- Via Indianapolis (IND)American Airlines and United Airlines, then Allegiant Air
- Via Knoxville (TYS)American Airlines and United Airlines, then Allegiant Air
- Via Orlando (MCO)American Airlines, Frontier Airlines and 1 more, then Breeze Airways
- Via Cincinnati (CVG)American Airlines and United Airlines, then Allegiant Air
- Via Asheville (AVL)United Airlines and American Airlines, then Allegiant Air
- Via Miami (MIA)American Airlines the whole way
- Via Charlotte (CLT)American Airlines the whole way
- Via Raleigh/Durham (RDU)American Airlines and United Airlines, then Breeze Airways
- Via Pittsburgh (PIT)American Airlines and United Airlines, then Allegiant Air
- Via Dulles (IAD)United Airlines the whole way
- Via Washington (DCA)American Airlines the whole way
- Via Philadelphia (PHL)American Airlines the whole way
- Via Houston (IAH)United Airlines the whole way
ORD to EYW: common questions
Which airlines fly nonstop from ORD to EYW?
American Airlines (oneworld) and United Airlines (Star Alliance) fly nonstop from Chicago (ORD) to Key West (EYW).
How far is Chicago from Key West by plane?
Chicago (ORD) and Key West (EYW) are 1,255 miles (2,019 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
Which points programs can book ORD to EYW award flights?
22 programs can book at least one of the nonstop airlines: Air Canada Aeroplan, Air New Zealand Airpoints, Alaska Atmos Rewards, American AAdvantage, ANA Mileage Club, Avianca LifeMiles, British Airways Club, Cathay Pacific Asia Miles and 14 more. Which flights each can book depends on its partners, so check the airline before you transfer points.
How many miles does ORD to EYW cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for ORD to EYW with taxes and fees.
Where can I connect between Chicago and Key West?
The most direct connections are through Atlanta (ATL), Tampa (TPA), Indianapolis (IND), Knoxville (TYS) and Orlando (MCO). On 12 of them the same airline flies both flights, for example Delta Air Lines through Atlanta.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.