Cheap Flights from San Diego (MYF) to Pittsfield (PSF)

Popular airlines from San Diego, CA (MYF-Montgomery Field) to Pittsfield, MA (PSF-Pittsfield Municipal)

Frequently asked questions

How much does a flight from San Diego, CA (MYF-Montgomery Field) to Pittsfield, MA (PSF-Pittsfield Municipal) cost?
Grab a cheap one-way flight or cheap return flight from San Diego, CA (MYF-Montgomery Field) to Pittsfield, MA (PSF-Pittsfield Municipal) 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 San Diego, CA (MYF-Montgomery Field) to Pittsfield, MA (PSF-Pittsfield Municipal)?
The cheapest month to fly from MYF to PSF is , when there's less demand. Off-peak season is often when you'll find cheap fares for travel between these airports.
What is the cheapest airline that flies from San Diego, CA (MYF-Montgomery Field) to Pittsfield, MA (PSF-Pittsfield Municipal)?
To find the cheapest airline that'll fly you from MYF to PSF, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from San Diego, CA (MYF-Montgomery Field) to Pittsfield, MA (PSF-Pittsfield Municipal)?
Nonstop flights from San Diego, CA (MYF-Montgomery Field) to Pittsfield, MA (PSF-Pittsfield Municipal) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MYF to PSF?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change 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 San Diego, CA (MYF-Montgomery Field) to Pittsfield, MA (PSF-Pittsfield Municipal)?
To avoid potential delays on the San Diego, CA (MYF-Montgomery Field) to Pittsfield, MA (PSF-Pittsfield Municipal) route, fly before 3 PM. Departures after this hour are 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.
Is it cheaper to buy a plane ticket from San Diego, CA (MYF-Montgomery Field) to Pittsfield, MA (PSF-Pittsfield Municipal) last-minute?
Holding off until just before your trip to book your flight from MYF to PSF generally means paying more. While you may find some last-minute deals, they aren't always guaranteed. Keep your travel plans flexible to maximize your chances of landing a bargain.
Is it cheaper to book a MYF to PSF flight and hotel package?
Securing a MYF to PSF flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our wide range of hotels and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from San Diego, CA (MYF-Montgomery Field) to Pittsfield, MA (PSF-Pittsfield Municipal)?
In most instances, you can modify or cancel your MYF to PSF flight. However, additional fees may apply, especially if you booked more than 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you want more information, head to our Customer Service portal.

Travel information

Origin airport
Montgomery Field
Destination airport
Pittsfield Municipal
Distance
2460 mi

Book with confidence

San Diego to Pittsfield Flights

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

 

The best time to book a flight from San Diego to Pittsfield

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

 

San Diego to Pittsfield Flights

Explore a world of travel with Expedia

*Available to One Key members.