Search Cheap Flights to
Windsor

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Windsor Flights as Low as $138

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Sat, May 3 - Tue, May 6
MCO
Orlando Intl.
ALB
Albany Intl.
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, May 3 from Orlando Intl. to Albany Intl., returning Tue, May 6, priced at $138 found 1 day ago
JetBlue Airways
Sat, May 3 - Wed, May 7
MCO
Orlando Intl.
ALB
Albany Intl.
$159 Roundtrip, found 1 day ago
$159
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, May 3 from Orlando Intl. to Albany Intl., returning Wed, May 7, priced at $159 found 1 day ago
Delta
Wed, Apr 30 - Mon, May 5
MCO
Orlando Intl.
ALB
Albany Intl.
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Apr 30 from Orlando Intl. to Albany Intl., returning Mon, May 5, priced at $168 found 1 day ago
Delta
Wed, Apr 23 - Thu, Apr 24
MCO
Orlando Intl.
ALB
Albany Intl.
$188 Roundtrip, found 4 days ago
$188
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Apr 23 from Orlando Intl. to Albany Intl., returning Thu, Apr 24, priced at $188 found 4 days ago
American Airlines
Wed, Apr 30 - Mon, May 5
MCO
Orlando Intl.
ALB
Albany Intl.
$194 Roundtrip, found 1 day ago
$194
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Apr 30 from Orlando Intl. to Albany Intl., returning Mon, May 5, priced at $194 found 1 day ago
Delta
Thu, May 1 - Tue, May 6
MCO
Orlando Intl.
ALB
Albany Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, May 1 from Orlando Intl. to Albany Intl., returning Tue, May 6, priced at $198 found 1 day ago
Delta
Wed, Apr 30 - Tue, May 6
MCO
Orlando Intl.
ALB
Albany Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Apr 30 from Orlando Intl. to Albany Intl., returning Tue, May 6, priced at $198 found 1 day ago
American Airlines
Wed, Apr 30 - Mon, May 5
MCO
Orlando Intl.
ALB
Albany Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Apr 30 from Orlando Intl. to Albany Intl., returning Mon, May 5, priced at $199 found 1 day ago
Delta
Thu, May 29 - Mon, Jun 2
ILM
Wilmington Intl.
ALB
Albany Intl.
$233 Roundtrip, found 1 day ago
$233
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, May 29 from Wilmington Intl. to Albany Intl., returning Mon, Jun 2, priced at $233 found 1 day ago
American Airlines
Tue, Jun 10 - Wed, Jul 30
LAX
Los Angeles Intl.
ALB
Albany Intl.
$327 Roundtrip, found 1 day ago
$327
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 10 from Los Angeles Intl. to Albany Intl., returning Wed, Jul 30, priced at $327 found 1 day ago
Delta
Mon, Apr 28 - Wed, Apr 30
PHX
Sky Harbor Intl.
ALB
Albany Intl.
$327 Roundtrip, found 1 day ago
$327
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Apr 28 from Sky Harbor Intl. to Albany Intl., returning Wed, Apr 30, priced at $327 found 1 day ago
United
Tue, Jun 10 - Wed, Jul 30
LAX
Los Angeles Intl.
ALB
Albany Intl.
$329 Roundtrip, found 1 day ago
$329
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jun 10 from Los Angeles Intl. to Albany Intl., returning Wed, Jul 30, priced at $329 found 1 day ago
Alaska Airlines
Tue, Jun 10 - Wed, Jul 30
LAX
Los Angeles Intl.
ALB
Albany Intl.
$447 Roundtrip, found 1 day ago
$447
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Jun 10 from Los Angeles Intl. to Albany Intl., returning Wed, Jul 30, priced at $447 found 1 day ago
American Airlines
Mon, Apr 14 - Fri, Apr 18
ORD
O'Hare Intl.
ALB
Albany Intl.
$474 Roundtrip, found 15 hours ago
$474
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Mon, Apr 14 from O'Hare Intl. to Albany Intl., returning Fri, Apr 18, priced at $474 found 15 hours ago
American Airlines
Wed, Apr 9 - Tue, Apr 15
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$494 Roundtrip, found 1 day ago
$494
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Apr 9 from Dallas-Fort Worth Intl. to Albany Intl., returning Tue, Apr 15, priced at $494 found 1 day ago
Delta
Sun, Apr 6 - Wed, Apr 9
DAL
Love Field
ALB
Albany Intl.
$601 Roundtrip, found 1 day ago
$601
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Apr 6 from Love Field to Albany Intl., returning Wed, Apr 9, priced at $601 found 1 day ago

Cheap Flights to Windsor

Fall in love at first flight with your vacation to Windsor by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Windsor on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Windsor, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Windsor

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Windsor with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the ALB airport.

What is the cheapest month to fly to Windsor?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Windsor are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Windsor?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Windsor.

What airport is best to fly into Windsor?

When you’re planning your trip to Windsor, convenience is the name of the game. Luckily, Windsor Pittsfield Municipal Airport is nearby so you can deplane and get going on checking off everything on your Windsor must-do list.

How much are flights to Windsor?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Windsor on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $138, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Windsor?

The trick to saving a stack of cash on your flight to Windsor? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $138 right now, why wait?

Windsor Flight Information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Roundtrip price
$138

Last Minute Hotel Deals in Windsor

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $108 per night from Apr 20 to Apr 21
$108
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (540 reviews)
"A motel style well thought out hotel, tastefully designed,very comfortable room with fabulous beds. Have no hesitation in recommending it."

Reviewed on Apr 2, 2025

Life House Berkshires
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is $99 per night from Apr 13 to Apr 14
$99
includes taxes & fees
Apr 13 - Apr 14
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,001 reviews)
"Love them"

Reviewed on Apr 1, 2025

The Yankee, Trademark Collection by Wyndham
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
The price is $147 per night from Apr 6 to Apr 7
$147
includes taxes & fees
Apr 6 - Apr 7
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
8.8/10 Excellent! (615 reviews)
"Clean and great location"

Reviewed on Mar 28, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
The price is $249 per night from Apr 6 to Apr 7
$249
includes taxes & fees
Apr 6 - Apr 7
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (434 reviews)
"조용하고 깨끗한 룸이 마음에 들었지만 힛팅 소리가 크게들려 중간에 잠이 깼다"

Reviewed on Apr 1, 2025

The Williams Inn
Hotel Downstreet, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
3 out of 5
40 Main St, North Adams, MA
The price is $141 per night from Apr 27 to Apr 28
$141
includes taxes & fees
Apr 27 - Apr 28
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (999 reviews)
"Great value."

Reviewed on Mar 29, 2025

Hotel Downstreet, Ascend Hotel Collection
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
The price is $178 per night from Apr 14 to Apr 15
$178
includes taxes & fees
Apr 14 - Apr 15
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,000 reviews)
"Historic property with a bunch to do. Pool was great!"

Reviewed on Mar 31, 2025

The Red Lion Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
The price is $103 per night from Apr 13 to Apr 14
$103
includes taxes & fees
Apr 13 - Apr 14
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,000 reviews)
"Excellent"

Reviewed on Mar 29, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
The price is $135 per night from Apr 20 to Apr 21
$135
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,792 reviews)
"The location to jimney peak was great."

Reviewed on Mar 26, 2025

Vacation Village in the Berkshires
See all 935 properties in Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.