United States · 295 miles (475 km)

Owensboro (OWB) to Chicago (ORD) flights

2 airlines fly nonstop from Owensboro (OWB) to Chicago (ORD): 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.

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Airlines flying nonstop from OWB to ORD

  • LF
    Contour AviationNot in an alliance
  • United Airlines logo
    United AirlinesStar Alliance · bookable with 13 programsWho books it

Book OWB to ORD with points

Loyalty programs that can book at least one of the nonstop airlines, from the Award Booking Guide.

OWB to ORD with one stop

2 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.

  • Via Charlotte (CLT)Contour Aviation, then American Airlines and United Airlines
    LF
    American Airlines logo
    United Airlines logo
  • Via Dulles (IAD)United Airlines the whole way
    United Airlines logo
    United Airlines logo

OWB to ORD: common questions

Which airlines fly nonstop from OWB to ORD?

Contour Aviation and United Airlines (Star Alliance) fly nonstop from Owensboro (OWB) to Chicago (ORD).

How far is Owensboro from Chicago by plane?

Owensboro (OWB) and Chicago (ORD) 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 OWB to ORD 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 OWB 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 OWB to ORD with taxes and fees.

Where can I connect between Owensboro and Chicago?

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

ORD to OWBEvery nonstop from OWBEvery nonstop from ORD

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.