Cheap flights from Chicago to Owensboro

Chicago FSS
CHI
Daviess County
OWB

Flight deals from Chicago to Owensboro

Below you can see the best deals on flights Chicago — Owensboro for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

Top 10 cheap flights from Chicago to Owensboro

About the Chicago — Owensboro flight

Looking for cheap flights from Chicago to Owensboro? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — Owensboro ticket online at the best price.

The route has direct flights — around 3 flights per week, flights are operated by Contour Airlines, a nonstop flight takes about 19 h 50 min, the distance between the cities is around 459 km.

Planning your trip? You may find our Owensboro travel guide, how to get from the airport into town and Owensboro weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

YesDirect flights
459 kmDistance
19 h 50 minTravel time
1Airlines
3 / wkFlights

Flight schedule from Chicago to Owensboro

The table shows direct flights from Chicago to Owensboro on the selected date. The flight takes approximately 19 h 50 min. Regular flights are operated by Contour Airlines. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Daviess County Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
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Last update: 01 Sep 2026

Prices by month

Average one-way fares from Chicago to Owensboro by month. Tickets are usually cheapest in July (around $63) and priciest in June (about $91) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$74lowMay$71lowSep$80medium
Feb$72lowJun$91highOct$87high
Mar$87highJul$63lowNov$69low
Apr$83highAug$85highDec$80medium

Some values are estimated based on seasonality.

When to fly

Weather in Owensboro: it is warmest in July (up to 31 °C on average) and coolest in January (around 6 °C). The driest month is September.

Temperature · Owensboro

Dry and wet days · Owensboro

Wind speed and direction · Owensboro

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How to get the best deal on a Chicago — Owensboro ticket

  • Book ahead: fares for Chicago — Owensboro are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Chicago is served by more than one airport — compare fares and travel time to each before you book.
  • Flights Chicago — Owensboro operate on Mondays, Tuesdays, Wednesdays, Thursdays and Fridays — keep that in mind when picking your travel dates.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Chicago — Owensboro route are operated by 1 airline; Contour Airlines runs the most flights (around 100% of all flights). Compare carriers, flight shares and schedules below.

  • Contour AirlinesLF
    1x/week
    WebsiteFleet: 39350k pax/year
    • Direct flight ORD → OWB1x/week
      Duration
      1h 30m
      Days
      MTWTFSS
    100.0%Open →

Cities and airports on the Chicago — Owensboro route

Flights Chicago — Owensboro depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Daviess County Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Owensboro

OWB
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Chicago — Owensboro flight

How long is the flight from Chicago to Owensboro?

A nonstop Chicago — Owensboro flight takes about 19 h 50 min — the distance between the cities is around 459 km.

How far is it from Chicago to Owensboro?

The distance from Chicago to Owensboro is about 459 km, which a nonstop flight covers in around 19 h 50 min.

Are there direct flights from Chicago to Owensboro?

Yes, there are nonstop flights Chicago — Owensboro — around 3 flights per week.

Which airlines fly from Chicago to Owensboro?

Airlines operating Chicago — Owensboro include Contour Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — Owensboro flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Daviess County Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to Owensboro?

The price of a Chicago — Owensboro ticket depends on your travel date, season and demand. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — Owensboro?

Flights Chicago — Owensboro are usually cheaper when booked in advance — a few weeks before departure and away from peak dates. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to Owensboro?

To catch a low fare Chicago — Owensboro, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Chicago

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New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverLondonNashvilleIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityPhoenixMiamiLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

Where else you can fly from Owensboro

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CharlotteSouth BendBirminghamManhattanLansingHartfordGreensboroKalamazoo

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