Cheap Flights from Chicago (ORD) to Pittsfield (PSF)

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Pittsfield, MA (PSF-Pittsfield Municipal)

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Pittsfield, MA (PSF-Pittsfield Municipal) cost?
Snag a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Pittsfield, MA (PSF-Pittsfield Municipal) 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 Pittsfield, MA (PSF-Pittsfield Municipal)?
The cheapest month to fly from ORD to PSF is , when demand is low. Off-peak months are generally when you'll find lower airfares between these airports.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Pittsfield, MA (PSF-Pittsfield Municipal)?
To find the cheapest airline flying from ORD to PSF, use Expedia's filter tool. Customize your search based on what matters most to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from O'Hare Intl. Airport (ORD) to Pittsfield, MA (PSF-Pittsfield Municipal)?
You'll need to catch a flight with a layover if you're traveling from O'Hare Intl. Airport (ORD) to Pittsfield, MA (PSF-Pittsfield Municipal). There are no daily direct flights on this route. However, just filter your search to include one or more stops to discover the best option for your trip.
What day of the week has the most flights from ORD to PSF?
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 O'Hare Intl. Airport (ORD) to Pittsfield, MA (PSF-Pittsfield Municipal)?
To touch down at Pittsfield, MA (PSF-Pittsfield Municipal) without delays, pick a flight that leaves O'Hare Intl. Airport (ORD) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**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 Pittsfield from O'Hare Intl. Airport (ORD)?
If you're traveling on a direct flight from O'Hare Intl. Airport (ORD) to Pittsfield, you can touch down at either Bradley Intl. Airport (BDL) or Albany Intl. Airport (ALB).
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Pittsfield, MA (PSF-Pittsfield Municipal) last-minute?
Booking your plane ticket from ORD to PSF just before your getaway is typically more expensive. However, if there's some wiggle room with your schedule, you could bag a cheap last-minute fare.
Is it cheaper to book an ORD to PSF flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORD to PSF flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one place will take the stress out of travel planning. Just secure your flights and choose from our wide range of hotels, then tailor your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Pittsfield, MA (PSF-Pittsfield Municipal)?
In most instances, you can modify or cancel your ORD to PSF flight. However, there may be additional charges, especially if you booked over 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you'd like more details, go to our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Pittsfield Municipal
Distance
747 mi

Book with confidence

Chicago to Pittsfield Flights

The cheapest times to fly from Chicago to Pittsfield

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

 

The best time to book a flight from Chicago to Pittsfield

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

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 Pittsfield 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 Pittsfield 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 Pittsfield 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 Pittsfield Flights

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*Available to One Key members.