Cheap Flights from Jamestown (JHW) to Chicago (PWK)

Popular airlines from Jamestown, NY (JHW-Chautauqua County) to Chicago, IL (PWK-Chicago Executive)

Frequently asked questions

How much does a flight from Chautauqua County Airport (JHW) to Chicago Executive Airport (PWK) cost?
Secure a cheap one-way flight or cheap return flight from Chautauqua County Airport (JHW) to Chicago Executive Airport (PWK) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Chautauqua County Airport (JHW) to Chicago Executive Airport (PWK)?
Traveling in is a great way to save, as it's the cheapest month for flights between JHW and PWK. You'll typically find the lowest fares during the off-season.
What is the cheapest airline that flies from Chautauqua County Airport (JHW) to Chicago Executive Airport (PWK)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll fly you from JHW to PWK. Then, sort your results by "Price (lowest to highest)" to score a great deal.
How many flights per day from Chautauqua County Airport (JHW) to Chicago Executive Airport (PWK)?
There aren't any daily direct flights departing from Chautauqua County Airport (JHW) to Chicago Executive Airport (PWK). 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 before you know it.
What day of the week has the most flights from JHW to PWK?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Chautauqua County Airport (JHW) to Chicago Executive Airport (PWK)?
To touch down at Chicago Executive Airport (PWK) without delays, pick a flight that leaves from Chautauqua County Airport (JHW) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**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.
Is it cheaper to buy a plane ticket from Chautauqua County Airport (JHW) to Chicago Executive Airport (PWK) last-minute?
Holding off until right before your break to book your flight from JHW to PWK generally means paying more. While you might find some last-minute offers, they aren't always guaranteed. Keep your travel schedule open to boost your chances of snagging a bargain.
Is it cheaper to book a JHW to PWK flight and hotel package?
Compared with arranging flights and hotels separately, booking a JHW to PWK 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 travel planning. Just pick your flights and choose from our wide range of stays, then personalize your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from Chautauqua County Airport (JHW) to Chicago Executive Airport (PWK)?
If you booked your JHW to PWK flight in the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you want more information.

Travel information

Origin airport
Chautauqua County
Destination airport
Chicago Executive
Distance
442 mi

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Jamestown to Chicago Flights

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

 

The best time to book a flight from Jamestown to Chicago

Sunday is one of the best days to book for cheap flights from Jamestown 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 Jamestown 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 Jamestown 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 Jamestown 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 Jamestown 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.

 

Jamestown to Chicago Flights

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*Available to One Key members.