Chicago (ORD) to Owensboro (OWB) flights
2 airlines fly nonstop from Chicago (ORD) to Owensboro (OWB): Contour Aviation and United Airlines. The two airports are 295 miles (475 km) apart. United Airlines is in Star Alliance. There are also 2 ways to fly it with one stop, through Charlotte and Dulles.
Airlines flying nonstop from ORD to OWB
- LFContour AviationNot in an alliance
- United AirlinesStar Alliance · bookable with 13 programsWho books it
Book ORD to OWB 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
- ANA Mileage ClubBooks United Airlines
- Avianca LifeMilesBooks United Airlines
- Emirates SkywardsBooks United Airlines
- EVA Air Infinity MileageLandsBooks United Airlines
- JetBlue TrueBlueBooks United Airlines
- Lufthansa Miles & MoreBooks United 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 OWB with one stop
2 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Charlotte (CLT)American Airlines and United Airlines, then Contour Aviation
LF - Via Dulles (IAD)United Airlines the whole way
ORD to OWB: common questions
Which airlines fly nonstop from ORD to OWB?
Contour Aviation and United Airlines (Star Alliance) fly nonstop from Chicago (ORD) to Owensboro (OWB).
How far is Chicago from Owensboro by plane?
Chicago (ORD) and Owensboro (OWB) are 295 miles (475 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 OWB award flights?
13 programs can book at least one of the nonstop airlines: Air Canada Aeroplan, Air New Zealand Airpoints, ANA Mileage Club, Avianca LifeMiles, Emirates Skywards, EVA Air Infinity MileageLands, JetBlue TrueBlue, Lufthansa Miles & More and 5 more. Which flights each can book depends on its partners, so check the airline before you transfer points.
How many miles does ORD to OWB 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 OWB with taxes and fees.
Where can I connect between Chicago and Owensboro?
The most direct connections are through Charlotte (CLT) and Dulles (IAD). On 1 of them the same airline flies both flights, for example United Airlines through Dulles.
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.