$41 Cheap flight deals from Pittsburgh (PIT) to Holyoke (SFY)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Pittsburgh to Holyoke

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jan 17 - Mon, Jan 19
PIT
Pittsburgh Intl.
BOS
Logan Intl.
$239 Roundtrip, found 7 hours ago
$239
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Sat, Jan 17 from Pittsburgh Intl. to Logan Intl., returning Mon, Jan 19, priced at $239 found 7 hours ago
Fri, Jan 16 - Mon, Jan 19
PIT
Pittsburgh Intl.
BDL
Bradley Intl.
$255 Roundtrip, found 9 hours ago
$255
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Fri, Jan 16 from Pittsburgh Intl. to Bradley Intl., returning Mon, Jan 19, priced at $255 found 9 hours ago

Airfares from $41 One Way, $82 Round Trip from Pittsburgh to Holyoke

Prices starting at $82 for return flights and $41 for one-way flights to Holyoke were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 30 - Fri, Feb 6
PIT
Pittsburgh
BDL
Hartford
$82 Roundtrip, found 4 days ago
$82
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jan 30 from Pittsburgh to Hartford, returning Fri, Feb 6, priced at $82 found 4 days ago
Fri, Jan 30 - Mon, Feb 2
PIT
Pittsburgh
BDL
Hartford
$87 Roundtrip, found 11 hours ago
$87
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Fri, Jan 30 from Pittsburgh to Hartford, returning Mon, Feb 2, priced at $87 found 11 hours ago
Wed, Feb 25 - Tue, Mar 3
PIT
Pittsburgh
BOS
Boston
$103 Roundtrip, found 8 hours ago
$103
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Wed, Feb 25 from Pittsburgh to Boston, returning Tue, Mar 3, priced at $103 found 8 hours ago
Mon, Mar 16 - Fri, Mar 20
PIT
Pittsburgh
BOS
Boston
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Mar 16 from Pittsburgh to Boston, returning Fri, Mar 20, priced at $117 found 5 days ago
Wed, Feb 25 - Sat, Feb 28
PIT
Pittsburgh
BOS
Boston
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Feb 25 from Pittsburgh to Boston, returning Sat, Feb 28, priced at $119 found 1 day ago

Holyoke economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Coach House
3.0-star property

The Coach House

9.6/10 Exceptional! (156 reviews)

Mar 4 - Mar 7

3 night stay

Pittsburgh (PIT) to Boston (BOS)

JetBlue Airways • Coach

Boston (BOS) to Pittsburgh (PIT)

Southwest Airlines • Coach
Price was $554, price is now $424 per person
$424
per person
found 17 hours ago
Doing all by phone and online is new to me so I’m still on the fence. Juggling my phone (which had the code for entrance lock) and lugging my suitcase up the entrance stairs and inside stairs was a challenge, not recommended for people with any accessibility needs. Beautiful property, without a doubt. Responsive staff via text messages and onsite parking was most helpful.

Reviewed on Nov 10, 2025

The Charles Hotel
4.0-star property

The Charles Hotel

9.4/10 Exceptional! (1,003 reviews)

Mar 7 - Mar 9

2 night stay

Pittsburgh (PIT) to Boston (BOS)

Delta • Coach

Boston (BOS) to Pittsburgh (PIT)

American Airlines • Coach
Price was $690, price is now $510 per person
$510
per person
found 21 hours ago
Great Cambridge hotel. Close to T stop and great location in Harvard Square. Lobby is a great place to read or get some work done. Rooms very comfortable.

Reviewed on Mar 31, 2025

The Whitney Hotel
4.0-star property

The Whitney Hotel

9.6/10 Exceptional! (482 reviews)

Mar 7 - Mar 9

2 night stay

Pittsburgh (PIT) to Boston (BOS)

Delta • Coach

Boston (BOS) to Pittsburgh (PIT)

American Airlines • Coach
Price was $668, price is now $508 per person
$508
per person
found 21 hours ago
What a gem in Boston! I've been to Boston many times and usually stay closer to the Downtown Crossing area. This time we stayed at the Whitney, choosing to try out that part of town. We loved it! Bigger than a boutique hotel, but small enough to feel intimate. Charles St is a great walking street, and we loved the location. The room was on the ground level (actually partly below ground) but was excellent! Well-appointed room, a good amount of space for Boston, and super professional staff. I'll be back when I come back to Boston

Reviewed on Jul 30, 2024

Don't see what you're looking for?
See all available trips from Pittsburgh to Holyoke
View all trips

More About Flying To Holyoke from Pittsburgh

Route Information for Flights from Pittsburgh to Holyoke

Origin Airport IATA Code
PIT
Destination Airport IATA Code
SFY
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Pittsburgh to Holyoke

Rack up your savings with low-cost flights from Pittsburgh to Holyoke with Orbitz On-the-Go. Orbitz On-the-Go offers mobile-only deals and cutting edge mobile tools to help you find bargain flights from Pittsburgh to Holyoke.

Mobile-Only Deals on Pittsburgh to Holyoke flights

Find guaranteed low prices on Pittsburgh to Holyoke flights using Orbitz On-the-Go. You can book discount domestic flights from Pittsburgh to Holyoke, and international tickets on Pittsburgh to Holyoke flights using our mobile site and apps.

Free Alerts Are No Surprise

Not only will you find cheap tickets on flights from Pittsburgh to Holyoke, but Orbitz free alerts will keep you up to speed on flight status, plus gate and baggage claim details. Receive instant updates via your choice of email, voice or text. Orbitz keeps you easily on task and on budget.

Share Itineraries on Flights from Pittsburgh to Holyoke

Are you traveling for business, pleasure or a combination of both? Keep family, friends and business contacts posted on flight and gate info. Just use MyTrips for iPhone, Android and web phones like Blackberry and Windows.

Add Smiles to Your Miles with Sales and Deals on Pittsburgh to Holyoke Flights

Travel planning is easy when you store your frequent flyer and loyalty program information on your Orbitz account. Then snag a low-fare air ticket on Pittsburgh to Holyoke flights, and you’re done. No muss, no fuss. Your miles will fly by with Orbitz On-the-Go cutting edge mobile tools and guaranteed low prices.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.