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Cheap flights from Owensboro (OWB) to Chicago (CHI)

OWB — CHI
jul. 8 — jul. 151
mar. 7/8
mar. 7/15
1 adult, Economy
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Cheap flight deals from Owensboro to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Owensboro (OWB) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated julio 3, 2025.

Popular in

April

Cheapest in

November

Average price

$152

Good round-trip deal

$142 or less
Highest demand for flights based on searches. 10% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Owensboro Daviess County to Chicago (CHI).
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Best time to book a flight from Owensboro to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Owensboro with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Owensboro to Chicago

What is the cheapest month to book a flight from Owensboro to Chicago?

Currently, August is the cheapest month in which you can book a flight from Owensboro to Chicago (average of $245). Flying from Owensboro to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OWB to CHI?

Find hourly flight availability from Owensboro to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julio 3, 2025.

A simple way to save on the total cost of your ticket is to fly from Owensboro to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 2% on your trip compared to booking a flight in the morning.

Weekly flight availability from Owensboro to Chicago

Explore weekly flight availability from Owensboro to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated julio 3, 2025.

The most flights from OWB to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

Related info for your journey

Find useful and relevant information for your journey from Owensboro to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Owensboro to Chicago?

    If you book a flight to Chicago from Owensboro, you will be flying from Daviess County, which is the city’s only airport. Owensboro Daviess County (OWB) is located 3.6 mi from the center of Owensboro. There is 1 flight from Daviess County to Chicago per day from 1 airline.

  • Can I find deals for flights from Owensboro to Chicago that include hotel bookings?

    Yes. In addition to deals on Owensboro to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Owensboro to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Owensboro to Chicago.

  • Can I find deals for business class flights from Owensboro to Chicago?

    Yes. Cheapflights offers flight deals from Owensboro to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Owensboro to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Owensboro to Chicago (average of $245). Flying from Owensboro to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Owensboro?

Book flights to Owensboro if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Top airline flying from Owensboro to Chicago

Discover the top airline that operate flights from Owensboro to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$113Average$143FlexibilityNo cancel feeOn-timeN/A

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