Key West (EYW) to Chicago (ORD) flights
2 airlines fly nonstop from Key West (EYW) to Chicago (ORD): 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 EYW to ORD
- American Airlinesoneworld · bookable with 9 programsWho books it
- United AirlinesStar Alliance · bookable with 13 programsWho books it
Book EYW to ORD 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
EYW to ORD 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)Breeze Airways, then American Airlines, Frontier Airlines and 1 more
- Via Indianapolis (IND)Allegiant Air, then American Airlines and United Airlines
- Via Knoxville (TYS)Allegiant Air, then American Airlines and United Airlines
- Via Orlando (MCO)Breeze Airways, then American Airlines, Frontier Airlines and 1 more
- Via Cincinnati (CVG)Allegiant Air, then American Airlines and United Airlines
- Via Asheville (AVL)Allegiant Air, then United Airlines and American Airlines
- Via Miami (MIA)American Airlines the whole way
- Via Charlotte (CLT)American Airlines the whole way
- Via Raleigh/Durham (RDU)Breeze Airways, then American Airlines and United Airlines
- Via Pittsburgh (PIT)Allegiant Air, then American Airlines and United Airlines
- 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
EYW to ORD: common questions
Which airlines fly nonstop from EYW to ORD?
American Airlines (oneworld) and United Airlines (Star Alliance) fly nonstop from Key West (EYW) to Chicago (ORD).
How far is Key West from Chicago by plane?
Key West (EYW) and Chicago (ORD) 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 EYW to ORD 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 EYW to ORD cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for EYW to ORD with taxes and fees.
Where can I connect between Key West and Chicago?
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.