Cheap Flights to Windsor: Windsor Flight Deals

View €120 flight on Sat, 15 Nov 2025Opens in a new window

Popular airlines to Windsor

    notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
    deals illustration

    Book smarter

    Save up to 15% on select hotels after you book a flight*
    trophy illustration

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap round-trip flights to Windsor

Prices were available within the past 7 days and start at €120 for one-way flights and €247 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 15 Nov - Sun, 16 Nov
DCA
Washington
MSN
Madison
€247 Return, found 16 hours ago
€247
Return
found 16 hours ago
Select American Airlines flight, departing Sat, 15 Nov from Washington to Madison, returning Sun, 16 Nov, priced at €247 found 16 hours ago
Delta
Sat, 15 Nov - Sun, 16 Nov
DCA
Washington
MSN
Madison
€298 Return, found 16 hours ago
€298
Return
found 16 hours ago
Select Delta flight, departing Sat, 15 Nov from Washington to Madison, returning Sun, 16 Nov, priced at €298 found 16 hours ago
United
Sat, 15 Nov - Sun, 16 Nov
DCA
Washington
MSN
Madison
€311 Return, found 16 hours ago
€311
Return
found 16 hours ago
Select United flight, departing Sat, 15 Nov from Washington to Madison, returning Sun, 16 Nov, priced at €311 found 16 hours ago
British Airways
Mon, 17 Nov - Mon, 24 Nov
DUB
Dublin
MSN
Madison
€677 Return, found 15 hours ago
€677
Return
found 15 hours ago
Select British Airways flight, departing Mon, 17 Nov from Dublin to Madison, returning Mon, 24 Nov, priced at €677 found 15 hours ago
KLM
Mon, 17 Nov - Mon, 24 Nov
DUB
Dublin
MSN
Madison
€733 Return, found 15 hours ago
€733
Return
found 15 hours ago
Select KLM flight, departing Mon, 17 Nov from Dublin to Madison, returning Mon, 24 Nov, priced at €733 found 15 hours ago

Find the cheapest month to fly from Columbus (CMH) to Madison (MSN)

April is typically the cheapest month to fly

From €169 - €409 per traveller.

Frequently asked questions

What is the name of Windsor's airport?
Organise a flight to Windsor and you'll be touching down at Dane County Regional Airport (MSN).
How far is Dane County Regional Airport (MSN) from central Windsor?
Dane County Regional Airport (MSN) is just a short cab ride from the bright lights of downtown Windsor. You'll find it 10 kilometres from the city centre.
What airport is best to fly into Windsor?
Located 10 kilometres from the centre of town, Truax Field will likely be your first stop in Windsor.
How many airlines fly to Windsor?
Windsor is serviced by 5 airlines from at least 16 airports across the globe.
Which airlines fly to Windsor?
United Airlines and American Airlines are some of the most sought-after airlines with flights to Windsor. Travellers often pick Chicago as a departure point with United Airlines flying this route the most.
How many nonstop flights are there to Windsor?
Flying to somewhere new is much easier when there aren't any annoying stopovers to slow you down. If you're heading to Windsor, the great news is that there are roughly 264 nonstop flights every week.
Where are the most popular flights to Windsor departing from?
Travellers often set off from Chicago, Minneapolis - St. Paul and Detroit airports when going to Windsor.
How long is the flight to Windsor Airport?
If it's Chicago you're departing, you'll be midair for around 1 hour and 6 minutes before you touchdown in Windsor. Terminal to terminal from Minneapolis - St. Paul takes around 1 hour and 12 minutes and from Detroit, it's 1 hour and 27 minutes.
How to book the cheapest flight to Windsor?
If you want to have some extra spending money on your Windsor holiday, listen up! As every experienced traveller will tell you, don't book at the very last minute. Fares are generally more expensive just prior to the departure date. Another great way to nab the best price is to shop around. If your destination has several airports, look into the cost of flying into a smaller terminal. And finally, remember that the early bird catches the worm. Know what a typical airfare costs and have your credit card ready to snap up a ticket as soon as you spot a bargain. The sweetest deals don't last long.
Do you have any tips for my flight to Windsor?
No matter where you're coming from, flying can be a seamless experience if you've prepared well enough. Follow these handy travel tips that will help get your Windsor holiday started on the right note. What to pack in your hand luggage:

  • Flying can be a pleasure if you've got all the right things. First things first, you'll need basic toiletry items, such as a toothbrush and some deodorant, a spare change of clothes and a magazine or two. Next, find a spot in your hand luggage for your electronic devices, chargers, any daily medications and maybe a blow-up neck pillow too. Lastly, and most importantly, be sure to bring your passport, travel papers and some cash.

Do not pack the following items in your hand luggage:

  • Squeeze all your full-sized bottles of hair gel and hairspray in your checked luggage. Any gels or liquids in your carry-on bag larger than 3.4 ounces (100 millilitres) will be confiscated by security. Sharp or pointed objects, like your beloved pocket knife, and dangerous products which are flammable or explosive, such as flares, bleaching agents and poisons, are also banned.

What to wear on a flight:

  • Go for comfort over style. Prepare for temperature changes in the cabin by layering up, and pick flat, slightly roomy footwear like sneakers.
  • You're probably aware of deep vein thrombosis (DVT), a blood clotting condition caused by prolonged periods of inactivity. To reduce your risk on board, drink lots of water, consider wearing compression tights or socks and move your lower limbs often.

How to get through airport security fast when flying to Windsor?
As savvy travellers know, the secret is to be organised before you arrive at the airport security gate. That way, you'll be stepping onto that plane to Windsor in next to no time. Follow these helpful tips and get your holiday off to a spectacular start:

  • First things first. Your travel ID and boarding pass will need to be inspected by airport security. Keep them at hand so you don't hold up the queue.
  • Next up is the X-ray machine. Remove anything on you that is likely to beep. This includes things like headphones or earphones, as well as bulky coats or jackets. They'll all need to go on the X-ray conveyor belt.
  • Your electronic devices like phones and laptops will also have to go on a tray for inspection. Don't worry, you'll be back online soon enough.
  • Remove all gels and liquids from your carry-on luggage. They usually need to be sent through the X-ray machine separately. Each product should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit in a quart-size (one litre), clear zip-close bag.
  • It's also possible you'll be asked to remove your shoes to be X-rayed, so wearing slip-on sneakers is always a clever idea.
  • Sharp items like knives can't be taken on board. They'll be seized at security, so pack them in your checked luggage.

Book with confidence

Book with confidence

Expedia.ie is an online travel company that specialises in securing the best prices for flights to Windsor. With Expedia you get highly specialised services, combining the best of technology, in-depth knowledge and the best connections in order to offer great deals to Windsor. Expedia shares your passion for travel and has built the best online travel service that promotes and encourages travel. Whether you are looking for cheap flights to Windsor, or are just on the lookout for the best flights to Windsor, you are sure to find the best deals with Expedia.ie.

"One of the many benefits of booking your flights through Expedia is that we are one of the world’s largest online travel agency, which means we use our collective experience and work tirelessly to bring you the best prices. With Expedia you get a user-friendly internet experience and a dedicated customer support service that ensures that everything goes smoothly. The goal of Expedia is to offer premium services at the lowest price, all at one single place. If you wish to save even more try combing a hotel in Windsor to your flight and create a personalised low cost city break or holiday to your favourite destination. Book early and you could save even more!

If you have an Expedia.ie itinerary number and have a question or concern about your travel plans you can call us on (01) 524 5005 from 8am - 10pm Monday to Friday, and 9am - 10pm at weekends and an Expedia agent will help you.

Travel information

Travel information

Destination airport
Dane County Regional
Destination airport IATA code
MSN
Destination city name
Madison
Return price
€246

Trending flights to Windsor

Prices were available within the past 7 days and start at €120 for one-way flights and €247 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, 19 Nov - Wed, 3 Dec
DUB
Dublin
MSN
Madison
€644 Return, found 5 days ago
€644
Return
found 5 days ago
Select American Airlines flight, departing Wed, 19 Nov from Dublin to Madison, returning Wed, 3 Dec, priced at €644 found 5 days ago

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to Expedia members.