
Popular airlines from Winchester to Pittsfield
- American Airlines
American Airlines
- Southwest Airlines
Southwest Airlines
- Delta
Delta
- JetBlue Airways
JetBlue Airways
- United
United
- Plan, book, fly with confidence
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Today's featured flight deals from Winchester to Pittsfield
Nonstop
Carry-on included
Lower price than typical
- Washington (IAD) to Albany (ALB).United, nonstop.Departing on Thu, Aug 28 at 5:15pm from Washington, arriving at 6:53pm in Albany.Returning on Mon, Sep 1 at 5:30am from Albany, arriving at 12:10pm in Washington.Select United flight departing on Thu, Aug 28 at 5:15pm from Washington, returning on Mon, Sep 1 at 5:30am from Albany priced at $39930% less than typical$399
- Washington (DCA) to Albany (ALB).American Airlines, nonstop.Departing on Tue, Sep 2 at 12:59pm from Washington, arriving at 2:27pm in Albany.Returning on Tue, Sep 9 at 6:00am from Albany, arriving at 7:34am in Washington.Select American Airlines flight departing on Tue, Sep 2 at 12:59pm from Washington, returning on Tue, Sep 9 at 6:00am from Albany priced at $19435% less than typical$194
- Washington (DCA) to Albany (ALB).American Airlines, nonstop.Departing on Tue, Sep 2 at 10:15am from Washington, arriving at 11:53am in Albany.Returning on Tue, Sep 9 at 5:29pm from Albany, arriving at 7:04pm in Washington.Select American Airlines flight departing on Tue, Sep 2 at 10:15am from Washington, returning on Tue, Sep 9 at 5:29pm from Albany priced at $22425% less than typical$224
- Washington (DCA) to Albany (ALB).American Airlines, nonstop.Departing on Tue, Sep 2 at 10:15am from Washington, arriving at 11:53am in Albany.Returning on Tue, Sep 9 at 6:00am from Albany, arriving at 7:34am in Washington.Select American Airlines flight departing on Tue, Sep 2 at 10:15am from Washington, returning on Tue, Sep 9 at 6:00am from Albany priced at $22425% less than typical$224
Cheap Flights from Winchester to Pittsfield (DCA-ALB)
Prices were available within the past 7 days and start at $90 for one-way flights and $177 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Nov 11 - Wed, Nov 12
IAD
Washington
ALB
Albany
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago

Wed, Nov 5 - Tue, Nov 11
BWI
Baltimore
ALB
Albany
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago

Thu, Sep 4 - Sat, Sep 6
DCA
Washington
ALB
Albany
$179 Roundtrip, found 1 hour ago
$179
Roundtrip
found 1 hour ago

Sun, Sep 7 - Tue, Sep 9
BWI
Baltimore
ALB
Albany
$181 Roundtrip, found 6 days ago
$181
Roundtrip
found 6 days ago

Sat, Oct 4 - Fri, Oct 24
IAD
Washington
ALB
Albany
$189 Roundtrip, found 1 hour ago
$189
Roundtrip
found 1 hour ago

Tue, Nov 4 - Wed, Nov 26
DCA
Washington
ALB
Albany
$219 Roundtrip, found 10 hours ago
$219
Roundtrip
found 10 hours ago
Find the cheapest month to fly from Washington (DCA) to Albany (ALB)
August is typically the cheapest month to fly
From $153 - $521 per traveler.
Graph displaying average flight prices per month
Alternative airports near Pittsfield
Prices were available within the past 7 days. Prices and availability are subject to change.
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