Cheap Flights from Owensboro to Chicago

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Flight deals from Owensboro to Chicago

Looking for a cheap last-minute deal or the best return flight from Owensboro Airport to Chicago? If you want to travel next month, return fares start from R 3,049. Find the lowest prices on one-way and return tickets right here.

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 July.

Direct flights from Owensboro to Chicago

Owensboro to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 1,523
Cheapest month to flyJuly
Average flight time1 hr, 44 mins
Most popular airlineContour Airlines
Average flights per week8

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 R 3,028. 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 44 minutes is the average flight time from Owensboro to Chicago.
Contour Airlines flies direct from Owensboro to Chicago.
As of June 2026, there are 8 flights per week flying from Owensboro to Chicago.
The cheapest month to fly from Owensboro to Chicago is usually July.
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 R 3,028.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Owensboro Airport to Chicago on Thursday, 30 July 2026.
Yes – the average flight time is 1 hour and 44 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.

Flying from Owensboro Daviess County Regional Airport (OWB) to Chicago: what you need to know

  • Expect to be in the air for 1 hour 30 minutes. On average, that's the duration of a direct flight from Owensboro Daviess County Regional Airport to Chicago.

  • Chicago and Owensboro (where Owensboro Daviess County Regional Airport is located) share the UTC-6 timezone. That means you won't need to account for any time differences.

  • The busiest route is from Owensboro Daviess County Regional Airport (OWB) to Chicago O'Hare International Airport (ORD). Take your pick of eight services every week between these two airports. Contour Airlines offers a 07:15 departure between OWB and ORD.

  • Leave enough time to get on your OWB to Chicago flight. As a general rule, turn up at least two hours before international departures and an hour ahead for domestic flights.

  • You can expect longer queues in popular months like July. Arriving up to four hours in advance for an international flight and two hours for domestic departures is a smart move.

  • Begin your trip at OWB and travel straight to Chicago O'Hare International Airport (ORD). That's where you can expect to touch down when searching for Owensboro Daviess County Regional Airport to Chicago tickets.

  • Contour Airlines is a popular airline that offers direct flights from Owensboro Daviess County Regional Airport to Chicago.

  • Located around 5 kilometres from the centre of Owensboro, OWB can be reached in about 15 minutes by car (depending on traffic). Travelling on public transport will take roughly 40 minutes.

  • Searching for a hotel close to OWB? If you're catching an early flight from Owensboro Daviess County Regional Airport to Chicago, these accommodation options will get you from your pillow to the plane in no time:

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

  • R 1,523 is the cheapest price we've seen for a one-way Owensboro Daviess County Regional Airport to Chicago flight. A round-trip ticket right now is R 3,028. Depending on the availability and when you book, these fares may change.

  • Don't leave everything to the last moment. You're more likely to find cheap flights from OWB to Chicago if you book ahead. Airlines often offer some excellent early bird rates.

  • The 'Whole month' search tool will show you the cheapest tickets from Owensboro Daviess County Regional Airport to Chicago across each month. It's a great way to find a bargain if your travel dates aren't set in stone.

  • Cut down on the time spent looking for cheap flights from OWB to Chicago by setting up a Price Alert. You'll get an email or push notification on the app when a lower fare pops up.

  • Snag an affordable flight from Owensboro Daviess County Regional Airport to Chicago with the help of our filters. Choose your ideal times, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) is around 27 kilometres from central Chicago. If you're opting for a ride-share or a taxi, the drive will take roughly 30 minutes.

  • If you're travelling on public transport, expect a journey time of about 45 minutes.

  • The last thing you need is a lengthy journey to your hotel if you're arriving on a late flight from Owensboro Daviess County Regional Airport to Chicago. Reserve one of these accommodation options near ORD instead:

  • Booking your ride from Chicago O'Hare International Airport about four weeks before your flight from OWB to Chicago can help you lock in the lowest rate.

  • The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Once your flight from Owensboro Daviess County Regional Airport to Chicago has hit the tarmac, you can reach the city centre in about 25 minutes by car. Central Chicago is roughly 16 kilometres from Chicago Midway International Airport (MDW).

  • The journey will take roughly 30 minutes on public transport.

  • You'll find some great places to rest your head close to MDW. Unwind and get cosy after your OWB to Chicago flight at one of these perfectly located options:

  • Avoid potential price surges. Securing your ride four weeks before your arrival at MDW will help you save.

  • You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is around 145 kilometres from the centre of Chicago. It takes about 1 hour 40 minutes to reach the city centre in a taxi or ride-share after your flight from Owensboro Daviess County Regional Airport to Chicago.

  • If you travel by public transport, the journey will take you around 2 hours.

  • Enjoy a more relaxed start to your break by staying at a hotel near RFD after your OWB to Chicago flight. Recover from a day of travel or simply give yourself time to settle into a new destination at:

  • If you're hoping for a specific make or model, booking early increases your chances of getting exactly what you want. Secure your ride from RFD at least a few weeks ahead of your flight from Owensboro Daviess County Regional Airport to Chicago.

  • Chicago Rockford International Airport can be found at 2 Airport Cir.

Best time to go to Chicago

  • July is the most popular month for flights from Owensboro Daviess County Regional Airport to Chicago. To avoid the crowds, head to Chicago in January.

  • Book a Owensboro Daviess County Regional Airport to Chicago plane ticket with a departure in July if you're eager to explore the city during its warmest month. You can expect temperatures to range from 16ºC (61ºF) to 28ºC (82ºF).

  • If you want cooler conditions, search for a cheap ticket from OWB to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of the United States

  • You've visited Chicago, now it's time to explore other parts of the United States. Journey about 451 kilometres southeast to Columbus to tick off its leading attractions. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, you've got a jam-packed schedule ahead.

  • If there's time to check out another well-known destination in the United States, head for Indianapolis, roughly 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are key highlights.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.