Cheap Flights from Chicago (ORD) to Olean (OLE)

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Olean, NY (OLE-Cattaraugus County)

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Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Olean, NY (OLE-Cattaraugus County) cost?
Secure a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Olean, NY (OLE-Cattaraugus County) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Olean, NY (OLE-Cattaraugus County)?
is the most affordable month to fly from ORD to OLE. Traveling outside of peak seasons is often the key to finding a great deal.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Olean, NY (OLE-Cattaraugus County)?
Use the filter tool on Expedia to compare different airlines and find the most affordable carrier that'll fly you from ORD to OLE. Then, sort your results by "Price (lowest to highest)" to score a good deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Olean, NY (OLE-Cattaraugus County)?
You'll have to take a flight with a layover if you're traveling from O'Hare Intl. Airport (ORD) to Olean, NY (OLE-Cattaraugus County). Direct flights don't operate daily on this route. However, simply filter your search to include one or two stops to find the best option for your trip.
What day of the week has the most flights from ORD to OLE?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can vary depending on the season, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Olean, NY (OLE-Cattaraugus County)?
Select a flight from O'Hare Intl. Airport (ORD) to Olean, NY (OLE-Cattaraugus County) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures after this time are on average 22% more likely to be 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 Hinsdale from O'Hare Intl. Airport (ORD)?
Check out your flight options from O'Hare Intl. Airport (ORD) to Buffalo Niagara Intl. Airport (BUF). This is the only airport in Hinsdale you can fly into if you're taking a direct flight.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Olean, NY (OLE-Cattaraugus County) last-minute?
Last-minute bookings from ORD to OLE are typically more expensive. To secure the lowest 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 right before your journey.
Is it cheaper to book an ORD to OLE flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORD to OLE flight and hotel package with Expedia could lead to significant savings. Better yet, having everything in one place takes the hassle out of planning your trip. Just secure your flights and select from our extensive range of hotels, then tailor your trip with extras like activities and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Olean, NY (OLE-Cattaraugus County)?
If you booked your ORD to OLE flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the fare type you purchased, 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
O'Hare Intl.
Destination airport
Cattaraugus County
Distance
488 mi

Book with confidence

Book with confidence

Chicago to Olean Flights

The cheapest times to fly from Chicago to Olean

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 Chicago to Olean are during the month of . You can find some of the cheapest flights from Chicago to Olean with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Olean

Sunday is one of the best days to book for cheap flights from Chicago to Olean: 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 Chicago to Olean

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 Chicago to Olean 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 Chicago to Olean 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 Chicago to Olean 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.

 

Chicago to Olean Flights

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*Available to One Key members.