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

OWB — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Popular in

April

Cheapest in

November

Average price

$137

Good round-trip deal

$138 or less

Good one-way deal

$95 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 September 2025
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Price to beat on a round-trip flight from Owensboro Daviess County to Chicago (CHI).
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Price to beat on a one-way 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 September 17, 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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 17, 2025.
Read reviews from past customers who have flown Contour from Owensboro to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Contour
7.2
Good
36 reviews

Comfort

7.0

Boarding

7.2

Food

6.5

Crew

7.6

Entertainment

6.1

Overall

7.2

Reviews

1 / 1
2.0
Mediocre

Kavita,Aug 2025

PAH - CLT

Flight was canceled after hours of delays due to a maintenance issue. Contour offered no assistance with rebooking, finding a hotel for the night, or transportation even though the next flight was not until the next morning.
Contour
7.2
Good
36 reviews
Contour
7.2
Good
36 reviews

Comfort

7.0

Boarding

7.2

Food

6.5

Crew

7.6

Entertainment

6.1

Overall

7.2

Reviews

1 / 1
2.0
Mediocre

Kavita,Aug 2025

PAH - CLT

Flight was canceled after hours of delays due to a maintenance issue. Contour offered no assistance with rebooking, finding a hotel for the night, or transportation even though the next flight was not until the next morning.

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.

  • What is the cheapest airline to fly from Owensboro to Chicago round-trip?

    Our cheapest airline available from Owensboro to Chicago is Contour. Our recent data shows that you can find tickets from as low as $113 on this airline. Contour is 22% cheaper than the average price of flights available within the next 90 days to this destination.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$113Average$144FlexibilityNo cancel feeOn-timeN/A

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