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 $147 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*
FCOGatwickJune 5 to June 8CA $147
FCOLondonJune 25 to June 27CA $315
JFKGatwickMay 29 to June 4CA $699
BOSGatwickMay 10 to May 14CA $731
BOSLondonMay 13 to June 1CA $799
SFOLondonMay 8 to May 21CA $811
PEKLondonJune 17 to June 18CA $889
SFOLondonMay 8 to May 21CA $955
LAXLondonMay 25 to June 9CA $1,185
MELGatwickMay 15 to June 5CA $1,201
SYDGatwickMay 24 to June 9CA $1,223
SFOGatwickMay 8 to May 21CA $1,280
SYDLondonJune 15 to June 24CA $1,325
MELLondonMay 25 to May 29CA $1,371
MELLondonMay 15 to June 5CA $1,921
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
FCOGatwickMay 3 to May 10CA $251
FCOLondonMay 3 to May 10CA $282
FCOLondonMay 3 to May 10CA $471
YYZGatwickMay 3 to May 10CA $704
LAXGatwickMay 4 to May 19CA $717
BOSLondonMay 3 to May 10CA $809
JFKLondonMay 3 to May 9CA $824
BOSLondonMay 3 to May 10CA $858
BOSGatwickMay 3 to May 10CA $890
YYZLondonMay 3 to May 11CA $1,008
JFKGatwickMay 3 to July 26CA $1,285
YYZLondonMay 3 to August 13CA $2,121
*Prices include taxes and fees

Your guide to flights to Windsor, ENG

WestJet, TAP Portugal 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 $147 and CA $2,121. Prices vary, but for the best fares, travel in June 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 $147. 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 January 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 $151 per night from May 30 to May 31
CA $151
CA $182 total
includes taxes & fees
May 30 - May 31
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! (1,006 reviews)
"We had a great stay. It was one of the best priced hotels locally, and we were really pleasantly surprised by the quality. The hotel is really well designed, the grounds are great, and the food in the buffet restaurant was really good with a menu that changed every night. It was also busy enough ..."

Reviewed on Apr. 28, 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 $198 per night from May 5 to May 6
CA $198
CA $237 total
includes taxes & fees
May 5 - May 6
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! (440 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 $220 per night from May 4 to May 5
CA $220
CA $265 total
includes taxes & fees
May 4 - May 5
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! (1,007 reviews)
"The staff were incredibly helpful and kind."

Reviewed on Apr. 25, 2025

Castle Hotel Windsor
Macdonald Windsor Hotel

Macdonald Windsor Hotel

4 out of 5
23 High Street, Windsor, England
The price is CA $219 per night from May 4 to May 5
CA $219
CA $263 total
includes taxes & fees
May 4 - May 5
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! (1,000 reviews)
Excellent location/very comfotable
"I had a lovely stay at this hotel. The location is excellent, staff helpful and friendly - especially the front desk and concierge, and the room was spacious with good amenities. It was very clean - I rarely take baths in hotels but felt comfortable doing so here. I felt it was a good value."

Reviewed on Apr. 27, 2025

Macdonald Windsor Hotel
Sir Christopher Wren Hotel

Sir Christopher Wren Hotel

4 out of 5
Thames Street, Windsor, England
The price is CA $240 per night from May 26 to May 27
CA $240
CA $287 total
includes taxes & fees
May 26 - May 27
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! (1,008 reviews)
"Fantastic place to stay :)"

Reviewed on Apr. 28, 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 $151 per night from May 30 to May 31
CA $151
CA $182 total
includes taxes & fees
May 30 - May 31
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! (1,006 reviews)
"We had a great stay. It was one of the best priced hotels locally, and we were really pleasantly surprised by the quality. The hotel is really well designed, the grounds are great, and the food in the buffet restaurant was really good with a menu that changed every night. It was also busy enough ..."

Reviewed on Apr. 28, 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 $151 per night from May 30 to May 31
CA $151
CA $182 total
includes taxes & fees
May 30 - May 31
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! (1,006 reviews)
"We had a great stay. It was one of the best priced hotels locally, and we were really pleasantly surprised by the quality. The hotel is really well designed, the grounds are great, and the food in the buffet restaurant was really good with a menu that changed every night. It was also busy enough ..."

Reviewed on Apr. 28, 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 $171 total
includes taxes & fees
May 5 - May 6
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,000 reviews)
"Everything was perfect. Could I get my 48$ refund that Expedia owes me thank you"

Reviewed on Apr. 30, 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 $113 per night from May 2 to May 3
CA $113
CA $136 total
includes taxes & fees
May 2 - May 3
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! (1,001 reviews)
"The staircase and features of this 600 year old building were unique"

Reviewed on Apr. 29, 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 $220 per night from May 4 to May 5
CA $220
CA $265 total
includes taxes & fees
May 4 - May 5
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! (1,007 reviews)
"The staff were incredibly helpful and kind."

Reviewed on Apr. 25, 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.
Treehouse Hotel London
Corinthia London
Mayfair – Peterson House
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Windsor flight + hotel packages - premium economy flights

Price found within the past 48 hours. Click for updated prices.
Oliver Plaza
The Langham, London
The Other House South Kensington
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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.
Three Falcons Hotel
Hotel Riu Plaza London Victoria
The Langham, London
Don't see what you're looking for?
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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.