Cheap Flights from Owensboro (OWB) to Chicago (MDW)

Popular airlines from Owensboro, KY (OWB-Owensboro-Daviess County Regional) to Chicago Midway Airport (MDW)

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Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $148
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $148

Frequently asked questions

How much does a flight from Owensboro-Daviess County Regional Airport (OWB) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight or cheap return flight from Owensboro-Daviess County Regional Airport (OWB) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Owensboro-Daviess County Regional Airport (OWB) to Midway Intl. Airport (MDW)?
is the most affordable month to fly from OWB to MDW. Traveling during quieter months is often the key to finding better fares.
What is the cheapest airline that flies from Owensboro-Daviess County Regional Airport (OWB) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from OWB to MDW, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Owensboro-Daviess County Regional Airport (OWB) to Midway Intl. Airport (MDW)?
There aren't any daily nonstop flights from Owensboro-Daviess County Regional Airport (OWB) to Midway Intl. Airport (MDW). But you can opt for flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds in no time at all.
What day of the week has the most flights from OWB to MDW?
You'll generally find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Owensboro-Daviess County Regional Airport (OWB) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Owensboro-Daviess County Regional Airport (OWB) to Midway Intl. Airport (MDW) route, travel before 3 PM. Flights after this time have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Owensboro-Daviess County Regional Airport (OWB)?
If you've booked a direct flight from Owensboro-Daviess County Regional Airport (OWB) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Owensboro-Daviess County Regional Airport (OWB) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from OWB to MDW are typically more expensive. To secure the best prices, start searching for flights as soon as possible. That said, if you're flexible with your travel plans, it's possible to score a cheap ticket just before your departure.
Is it cheaper to book an OWB to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking an OWB to MDW flight and hotel package with Expedia could result in significant savings. Better still, having everything in one easy place will take the stress out of planning your trip. Simply pick your flights and select from our wide range of hotels, then customize your trip with other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Owensboro-Daviess County Regional Airport (OWB) to Midway Intl. Airport (MDW)?
If you booked your OWB to MDW flight within the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of fare you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more information.

Travel information

Travel information

Origin airport
Owensboro-Daviess County Regional
Destination airport
Midway Intl.
Distance
280 mi

Book with confidence

Book with confidence

Owensboro to Chicago Flights

The cheapest times to fly from Owensboro to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Owensboro to Chicago are during the month of . You can find some of the cheapest flights from Owensboro to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Owensboro to Chicago

Sunday is one of the best days to book for cheap flights from Owensboro to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Owensboro to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Owensboro to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Owensboro to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Owensboro to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Owensboro to Chicago Flights

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