Cheap Flight Deals to Windsor ENG from CA $329

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How to find cheap flights to Windsor?

The cheapest prices found with in the last 7 days for return flights were CA $542 and CA $329 for one-way flights to Windsor for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
LAXGatwickMay 4 to May 18CA $542
BOSGatwickMay 5 to May 13CA $756
BOSLondonApril 24 to May 7CA $757
SFOLondonMay 7 to May 13CA $844
PEKGatwickJune 12 to June 28CA $903
SFOLondonApril 28 to May 13CA $904
LAXLondonApril 23 to May 6CA $908
PEKLondonMay 24 to May 28CA $953
SFOGatwickMay 9 to May 22CA $1,057
SYDGatwickMay 11 to May 26CA $1,205
MELGatwickMay 5 to May 18CA $1,233
SYDLondonMay 12 to May 26CA $1,268
MELLondonMay 22 to May 28CA $1,556
MELLondonMay 22 to May 28CA $1,837
PEKLondonJune 20 to June 24CA $2,535
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
BOSLondonApril 18 to April 24CA $808
JFKGatwickApril 18 to April 24CA $826
YYZLondonApril 20 to April 24CA $834
JFKLondonApril 18 to April 22CA $840
LAXLondonApril 20 to May 6CA $1,136
BOSLondonApril 20 to May 2CA $1,190
YYZGatwickApril 20 to April 24CA $1,252
JFKLondonApril 20 to April 29CA $1,494
YYZLondonApril 20 to April 24CA $1,633
LAXLondonApril 20 to May 13CA $3,791
*Prices include taxes and fees

Your guide to flights to Windsor, ENG

WestJet, Air Transat fly to Windsor, so use Travelocity to search, find, and compare some truly tempting deals from the 3 airlines—that way you can be sure you’ve found the best deal for you. A flight to Windsor ENG currently costs between CA $542 and CA $3,791. Prices vary, but for the best fares, travel in May when prices are at their lowest.  

Top tips for finding cheap flights to Windsor  

The cheapest flight for a round trip to Windsor is currently CA $542. When you search for flights to Windsor, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Windsor for nearby days.  The cheapest month to travel to Windsor is June from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Windsor 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Windsor with Travelocity 

We have top deals on plane tickets even for last minute flights to Windsor, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Windsor for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Windsor

De Vere Beaumont Estate

De Vere Beaumont Estate

4 out of 5
Burfield Road, Berkshire, Windsor, England
The price is CA $136 per night from May 5 to May 6
CA $136
CA $163 total
includes taxes & fees
May 5 - May 6
Stay at this 4-star eco-certified hotel in Windsor. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (1,002 reviews)
"Nice hotel well looked after !! Staff were lovely and the Resturant /bar was great !! Would definitely recommend to family and friends!! 👍"

Reviewed on Apr. 7, 2025

De Vere Beaumont Estate
The Royal Adelaide Hotel

The Royal Adelaide Hotel

3.5 out of 5
46 Kings Road, Windsor, England
The price is CA $210 per night from Apr. 21 to Apr. 22
CA $210
CA $252 total
includes taxes & fees
Apr 21 - Apr 22
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (438 reviews)
"Staff were friendly and the rooms were very comfortable."

Reviewed on Apr. 6, 2025

The Royal Adelaide Hotel
New Oscar

New Oscar

2 out of 5
65 Vansittart Road, Windsor, England
Stay at this B&B in Windsor. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Popular attractions Windsor Castle and LEGOLAND® Windsor are located ...
5.8/10 (73 reviews)
£10 car parking fee a surprise!
"The hotel is clean and comfortable but we were surprised by the £10 parking fee to use the car park behind the hotel. There’s no option as parking on the street is restricted"

Reviewed on Oct. 6, 2019

New Oscar
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The Union Inn

The Union Inn

4 out of 5
Crimp Hill, Windsor, England
Stay at this 4-star inn in Windsor. Enjoy free parking, breakfast (surcharge), and a bar/lounge. Popular attractions Windsor Castle and LEGOLAND® Windsor are ...
7.8/10 Good! (489 reviews)
Our stay
"The food was good, welcome was very friendly and the bed comfortable."

Reviewed on Oct. 23, 2023

The Union Inn
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.

Luxury Hotels in Windsor

Castle Hotel Windsor

Castle Hotel Windsor

4 out of 5
18 High Street, Windsor, England
The price is CA $218 per night from Apr. 27 to Apr. 28
CA $218
CA $262 total
includes taxes & fees
Apr 27 - Apr 28
Stay at this 4-star luxury hotel in Windsor. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,002 reviews)
A comfortable stay
"Very nice room, comfortable bed, lots of choice with tea, coffee etc in the room. For us, the breakfast was a bit of a let down, greasy overcooked hash browns, average quality sausages, tepid beans. I would have expected to have been served at our table as opposed to self service. Having said that, ..."

Reviewed on Apr. 13, 2025

Castle Hotel Windsor
Macdonald Windsor Hotel

Macdonald Windsor Hotel

4 out of 5
23 High Street, Windsor, England
The price is CA $202 per night from Apr. 27 to Apr. 28
CA $202
CA $242 total
includes taxes & fees
Apr 27 - Apr 28
Stay at this 4-star eco-certified hotel in Windsor. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the breakfast and the ...
8.6/10 Excellent! (1,005 reviews)
"Great hotel to stay in!"

Reviewed on Apr. 13, 2025

Macdonald Windsor Hotel
Sir Christopher Wren Hotel

Sir Christopher Wren Hotel

4 out of 5
Thames Street, Windsor, England
The price is CA $235 per night from Apr. 19 to Apr. 20
CA $235
CA $282 total
includes taxes & fees
Apr 19 - Apr 20
Stay at this 4-star business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and 24-hour room service. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,003 reviews)
"Lovely hotel, staff very helpful and accommodating to my individual needs. Right in the middle of town near all amenities"

Reviewed on Apr. 12, 2025

Sir Christopher Wren Hotel
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De Vere Beaumont Estate

De Vere Beaumont Estate

4 out of 5
Burfield Road, Berkshire, Windsor, England
The price is CA $136 per night from May 5 to May 6
CA $136
CA $163 total
includes taxes & fees
May 5 - May 6
Stay at this 4-star eco-certified hotel in Windsor. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (1,002 reviews)
"Nice hotel well looked after !! Staff were lovely and the Resturant /bar was great !! Would definitely recommend to family and friends!! 👍"

Reviewed on Apr. 7, 2025

De Vere Beaumont Estate
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.

Family Friendly Hotels in Windsor

De Vere Beaumont Estate

De Vere Beaumont Estate

4 out of 5
Burfield Road, Berkshire, Windsor, England
The price is CA $136 per night from May 5 to May 6
CA $136
CA $163 total
includes taxes & fees
May 5 - May 6
Stay at this 4-star eco-certified hotel in Windsor. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (1,002 reviews)
"Nice hotel well looked after !! Staff were lovely and the Resturant /bar was great !! Would definitely recommend to family and friends!! 👍"

Reviewed on Apr. 7, 2025

De Vere Beaumont Estate
Holiday Inn Express Windsor by IHG

Holiday Inn Express Windsor by IHG

3 out of 5
71 Alma Road, Windsor, England
The price is CA $142 per night from May 5 to May 6
CA $142
CA $170 total
includes taxes & fees
May 5 - May 6
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,003 reviews)
"Very friendly staff. Newly remodeled rooms. Good warm breakfast included. Very nice bathroom. Easy walk to Windsor castle and shopping areas. Will come back here again. 10/10"

Reviewed on Apr. 14, 2025

Holiday Inn Express Windsor by IHG
The Crown And Cushion

The Crown And Cushion

3 out of 5
84 High Street, Windsor, England
The price is CA $116 per night from Apr. 17 to Apr. 18
CA $116
CA $140 total
includes taxes & fees
Apr 17 - Apr 18
Stay at this 3-star inn in Windsor. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Windsor Castle and LEGOLAND® Windsor are ...
9/10 Wonderful! (1,002 reviews)
"Lovely nights stay great location. Food and breakfast great. The pillows were abit hard. Everything else great."

Reviewed on Apr. 13, 2025

The Crown And Cushion
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Castle Hotel Windsor

Castle Hotel Windsor

4 out of 5
18 High Street, Windsor, England
The price is CA $218 per night from Apr. 27 to Apr. 28
CA $218
CA $262 total
includes taxes & fees
Apr 27 - Apr 28
Stay at this 4-star luxury hotel in Windsor. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,002 reviews)
A comfortable stay
"Very nice room, comfortable bed, lots of choice with tea, coffee etc in the room. For us, the breakfast was a bit of a let down, greasy overcooked hash browns, average quality sausages, tepid beans. I would have expected to have been served at our table as opposed to self service. Having said that, ..."

Reviewed on Apr. 13, 2025

Castle Hotel 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.

Best Windsor Flight and Hotel Packages

Windsor flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Colonnade Hotel London
Chapter Westminster
The Princes Residences
Don't see what you're looking for?
See all available trips from Toronto to Windsor
View all trips

Windsor flight + hotel packages - premium economy flights

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza London Victoria
1 Hotel Mayfair
The Langham, London
Don't see what you're looking for?
See all available trips from Toronto to Windsor
View all trips

Windsor flight + hotel packages - business class flights

Price found within the past 48 hours. Click for updated prices.
The Langham, London
The Savoy
Corinthia London
Don't see what you're looking for?
See all available trips from Vancouver to Windsor
View all trips

Need a car after flight to Windsor?

Plane Tickets To Windsor

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Windsor. Browse through our inventory to explore a wide range of cheap flights to Windsor to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Windsor as you anxiously await to exit the plane and explore what Windsor has to offer. Considering all the amazing local food and culture in Windsor, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Windsor to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Windsor without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Windsor with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Windsor today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.