HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

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

OWB — CHI
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Owensboro to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find 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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Popular in

April

Cheapest in

January

Average price

$156

Good round-trip deal

$100 or less

Good one-way deal

$44 or less
Provider with most accurate pricing for Owensboro Daviess County-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Owensboro Daviess County-Chicago (CHI) flights.
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Owensboro Daviess County to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Owensboro Daviess County to Chicago (CHI).
Search Deals

Compare providers for flights from Owensboro to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Owensboro to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Owensboro-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Owensboro-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Owensboro-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Owensboro-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Owensboro-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, September is the cheapest month in which you can book a flight from Owensboro to Chicago (average of $77). Flying from Owensboro to Chicago in July is currently the most expensive (average of $139). 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 December 28, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Owensboro to Chicago as you normally would.

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 December 28, 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
7.6
Good
43 reviews

Boarding

7.6

Entertainment

6.1

Crew

7.9

Comfort

7.3

Overall

7.6

Food

6.9

Reviews

1 / 2
10.0
Excellent

Anonymous,Oct 2025

CLT - PAH

The steward on my flight from Charlotte to Paducah was the kindest person I’ve ever met. He made everyone feel comfortable, and even laugh a little. Not to mention his hair was top tier. He deserves a raise. Xoxo
Contour
7.6
Good
43 reviews
Contour
7.6
Good
43 reviews

Boarding

7.6

Entertainment

6.1

Crew

7.9

Comfort

7.3

Overall

7.6

Food

6.9

Reviews

1 / 2
10.0
Excellent

Anonymous,Oct 2025

CLT - PAH

The steward on my flight from Charlotte to Paducah was the kindest person I’ve ever met. He made everyone feel comfortable, and even laugh a little. Not to mention his hair was top tier. He deserves a raise. Xoxo

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 $109 on this airline. Contour is 28% 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, September is the cheapest month in which you can book a flight from Owensboro to Chicago (average of $77). Flying from Owensboro to Chicago in July is currently the most expensive (average of $139). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Owensboro to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Nashville to O'Hare Intl flights
Cincinnati to O'Hare Intl flights
Nashville to Midway flights
Knoxville to O'Hare Intl flights
Cincinnati to Midway flights
Louisville to O'Hare Intl flights
Lexington to O'Hare Intl flights
Nashville to St. Louis flights
Cincinnati to St. Louis flights
Louisville to Midway flights
Knoxville to Midway flights
Blountville to O'Hare Intl flights
Lexington to Midway flights
Nashville to Rockford flights
Nashville to Moline flights
Cincinnati to Rockford flights
Blountville to Midway flights
Knoxville to St. Louis flights
Lexington to St. Louis flights
Evansville to O'Hare Intl flights
Cincinnati to Moline flights
Knoxville to Peoria flights
Louisville to St. Louis flights
Lexington to Rockford flights
Huntington to O'Hare Intl flights
Paducah to O'Hare Intl flights
Lexington to Moline flights
Cincinnati to Evansville flights
Knoxville to Bloomington flights
Louisville to Moline flights
Knoxville to Moline flights
Evansville to Midway flights
Owensboro to St. Louis flights
Blountville to Bloomington flights
Nashville to Quincy flights
Blountville to St. Louis flights
Nashville to Springfield flights
Nashville to Paducah flights
Nashville to Dubuque flights

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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$109Average$156FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.