Cheap Flights from Owensboro to Chicago

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Find the cheapest month to fly from Owensboro to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Owensboro to Chicago flights are currently cheapest in August.

Direct flights from Owensboro to Chicago

Alternative Owensboro to Chicago routes

Looking for the cheapest, fastest or easiest route from Owensboro to Chicago? You could fly into the following airports instead.

Owensboro to Chicago: Flight information

The things to know before you go.
Cheapest flight foundر.ق.‏ 262
Cheapest month to flyAugust
Average flight time1 hr, 35 mins
Most popular airlineContour Airlines
Average flights per week12

Finding cheap flights from Owensboro to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Owensboro to Chicago is ر.ق.‏ 524. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
1 hour and 35 minutes is the average flight time from Owensboro to Chicago.
Contour Airlines flies direct from Owensboro to Chicago.
As of June 2025, there are 12 flights per week flying from Owensboro to Chicago.
The cheapest month to fly from Owensboro to Chicago is usually June 2025.
If you're flying from Owensboro Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from ر.ق.‏ 524.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Owensboro Airport to Chicago on Saturday, 16 August 2025.
Yes – the average flight time is 1 hour and 35 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In June, the average temperature is usually around 19°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Contour Airlines offers the cheapest flight tickets to Chicago.

Travelling from Daviess County Airport (OWB) to Chicago: what you need to know

  • Expect to be in the air for 1 hour 30 minutes. That's the average time for a direct flight from Daviess County Airport to Chicago.

  • Chicago and Owensboro (where Daviess County Airport is located) share the UTC-5 timezone. This means you won't have to change your watch on arrival.

  • With 12 flights a week between the two airports, Daviess County Airport (OWB) to O'Hare International Airport (ORD) is the busiest route. Contour Airlines operates the earliest flight at 07:15. If you prefer to get more out of your day before jetting off, the latest departure from OWB to ORD is with Contour Airlines at 14:00.

  • For stress-free travel, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This will give you plenty of time to board your OWB to Chicago flight.

  • Longer lines at security and check-in are likely if you're heading away during high season, so allow a little extra breathing room. A good general rule for peak periods? Get there up to four hours ahead for international flights and two hours for domestic departures.

  • You can book a direct Daviess County Airport to Chicago ticket. Start your journey at OWB and land at O'Hare International Airport (ORD).

  • Get on board with Contour Airlines. This well-known airline offers direct flights from Daviess County Airport to Chicago.

  • Central Owensboro to OWB is around 5 kilometres. Depending on traffic conditions, it'll take you about 10 minutes to get there if you're ride-sharing, catching a cab or driving.

  • Planning to catch an early flight from Daviess County Airport to Chicago? Avoid the stress of rushing to the terminal (and sneak in some extra snooze time) by choosing one of these hotels near OWB:

How to find the cheapest flights from Daviess County Airport (OWB) to Chicago

  • ر.ق.‏ 262 is the lowest price we've seen for a one-way Daviess County Airport to Chicago flight. A round-trip flight ticket right now is ر.ق.‏ 524. Depending on when you want to go and the availability, these fares can change.

  • Book one month before you travel. Pricing trends show that this is the ideal window for finding cheap flights from OWB to Chicago.

  • The best month for finding cheap Daviess County Airport to Chicago tickets is May. Use the 'Whole month' tool to compare prices, then select the dates that offer the lowest fares.

  • Spend less time searching for cheap flights from OWB to Chicago by setting up a Price Alert. You'll receive an email or notification through the app when a lower fare becomes available.

  • Find an affordable flight from Daviess County Airport to Chicago with the help of our filters. Select your preferred departure time, duration and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to the centre of Chicago takes around 35 minutes to reach by car. The centre is roughly 40 kilometres away.

  • Getting there on public transport typically takes 55 minutes.

  • If you're arriving on a late flight from Daviess County Airport to Chicago, few things beat the convenience of staying close to the terminal. Grab your luggage from the carousel and then be showered and snoozing soon after at one of these accommodation options near ORD:

  • Pick up an O'Hare International Airport rental car and explore Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are popular providers to choose from here.

  • To get the lowest price, book your ride from O'Hare International Airport around four weeks in advance of your flight from OWB to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is roughly 19 kilometres from the centre of Chicago. Once you've disembarked your flight from Daviess County Airport to Chicago, it'll take you around 20 minutes to reach the heart of the city in a ride-share or cab.

  • You can expect the trip to take about 45 minutes on public transport.

  • Hang up the 'Do not disturb' sign and relax at a hotel close to MDW. Here are a few options where you can check in after your OWB to Chicago flight:

  • No time to waste? The fastest way to get to where you're going is with a Chicago Midway International Airport rental car. Pick up a set of wheels from Dollar, Hertz or Budget and be on your way in a flash.

  • Lock in the lowest price by reserving your ride from MDW four weeks in advance. You'll also have access to a wider selection of vehicles.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 137 kilometres from the centre of Chicago. It takes about 1 hour 25 minutes to get to the city centre by cab or ride-share after your flight from Daviess County Airport to Chicago.

  • Public transport will get you there in about 4 hours 15 minutes.

  • Enjoy a restful, unhurried start to your trip by checking in to a hotel near RFD after your OWB to Chicago flight. Recharge after a day of travel or simply give yourself time to settle into a new destination at:

  • Whether you're looking for a zippy compact for a solo getaway or a spacious SUV to transport your group, you'll find the ideal Chicago Rockford International Airport rental car for you. Browse the range of wheels available here from providers such as Budget, Alamo and National.

  • Rental companies sometimes offer promotions for early bookings, so reserve your ride from RFD a few weeks ahead of your flight from Daviess County Airport to Chicago. A little prep work can make a big difference in cost.

  • Chicago Rockford International Airport's street address is 2 Airport Cir.

Best time to go to Chicago

  • Travel to Chicago during peak season if you prefer a bustling atmosphere, but remember that hotel prices may be higher. Alternatively, book flights from Daviess County Airport to Chicago in the low season when prices are cheaper and it's quieter.

  • Before locking in your Daviess County Airport to Chicago flight ticket, think about what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 15ºC to 29ºC.

  • January has average temperatures of between -12ºC and 3ºC. Search for a cheap ticket from OWB to Chicago around that time if you want to travel in cooler conditions.

More about Chicago

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometres away to the south-east, its best attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another standout destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without dropping by The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.