Beginning of main content

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Fares from $59 One Way, $97 Round Trip from Owensboro to Chicago

Prices starting at $97 for return flights and $59 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Need A Hotel In Chicago?

Hotels In Top Chicago Neighborhoods

Near North Side
261 hotels

Loews Chicago Hotel

4.5 out of 5.0


The Loop
186 hotels


South Loop
158 hotels

Congress Plaza Hotel

3.5 out of 5.0


Stay Near Exciting Chicago Attractions

More About Flying To Chicago from Owensboro

Route Information for Flights from Owensboro to Chicago

Origin Airport IATA CodeEVV
Destination Airport IATA CodeCHI
Distance272 mi
Direct Flight AirlinesANA, United Airlines
Earliest Flight Arrival2:57PM UTC
Latest Flight Arrival2:57PM UTC

Flights Review

Jan 20, 2020

The most customer serviced oriented airline I’ve EVER flown! When our plane had mechanical difficulties, the airline employees kept us constantly informed about what was going on and then when the time lengthened they brought out bottled water and snacks . Also the timely text messages received also kept us informed and also conveyed their understanding that this was not what we had planned... we were treated with such respect and as though we mattered in the scheme of things. The United airline employees went above and beyond what other airlines think is important!!! THANK YOU UNITED!!!!

Dec 16, 2019

We could not hear a single word that the flight attendant said when she was making announcements.

Sep 21, 2018

If it wasn’t for bad weather in MN it would all have been good but you cannot control that

Jul 29, 2018

I haven't flown in a while and was surprised that flight attendants no longer read off the gate numbers for connecting flights. No one is around at the deplaning gate to provide information about locations and gate numbers. Yes, of course, the gates are displayed in various places, but when you are in a hurry, you lose precious minutes.

Owensboro to Chicago

The perfect trip begins with Orbitz. From booking your flights from Owensboro to Chicago to finding the best hotels, Orbitz has got it covered.

Stress-free Searching

With an easy to use system, Orbitz takes the stress and expense out of travel. Not only does Orbitz match your Owensboro to Chicago flights to your ideal hotel, the Display Matrix shows your deals and discounts, including free nights and other savings.

Be One Step Ahead

Need to know what is going on at the airport before you get there? With Orbitz’s free alerts service, you can quickly find out about any booking changes, or flight from Owensboro to Chicago disruptions, saving you hours of wasted time. And if you are being picked up at the airport after your Owensboro to Chicago flights, have alerts sent straight to your contact’s mobile phone or email.

Cutting-Edge Mobile Tools

Find the best price on flights from Owensboro to Chicago with Orbitz’s mobile apps for iPhone and Android. Use on your mobile browser to check your gate, baggage allowance and delays, or find exclusive deals on hotels only available to mobile users.

We Work, you Rest and Play

Not only does booking with us ensure guaranteed low prices, but Orbitz does the hard work, leaving you to relax. Just tell us what you want, from Owensboro to Chicago flights, to great deals on hotels and car rental, and activities and tours, and we will do all the rest.

Flights from Owensboro to Chicago - Frequently Asked Questions

What is the shortest flight from Owensboro to Chicago?

If the weather is good and all goes according to plan, you could be landing at Chicago, IL Airport (MDW-Midway Intl.) from Owensboro, KY Airport (OWB-Owensboro-Daviess County Regional) in just 2 hours and 19 minutes. With such a quick flight time, think about traveling with hand luggage only.

^Savings based on all package bookings with Flight + Hotel made on from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.