A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

Cheap Flights to Windsor , WI from CA $260

View CA $260 flight on Wed, Aug 5, 2026Opens in a new window

Popular airlines to Windsor

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How much is the cheapest flight to Windsor?

Prices were available within the past 7 days and start at CA $260 for one-way flights and CA $399 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Aug 19 - Sat, Aug 22
BNA
Nashville
MSN
Madison
CA $399 Roundtrip, found 3 days ago
CA $399
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Aug 19 from Nashville to Madison, returning Sat, Aug 22, priced at CA $399 found 3 days ago
American Airlines
Tue, Jun 30 - Tue, Jul 7
BUF
Buffalo
MSN
Madison
CA $433 Roundtrip, found 6 days ago
CA $433
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Jun 30 from Buffalo to Madison, returning Tue, Jul 7, priced at CA $433 found 6 days ago
United
Wed, Jul 8 - Tue, Jul 14
YHZ
Halifax
MSN
Madison
CA $474 Roundtrip, found 15 hours ago
CA $474
Roundtrip
found 15 hours ago
Select United flight, departing Wed, Jul 8 from Halifax to Madison, returning Tue, Jul 14, priced at CA $474 found 15 hours ago
WestJet
Wed, Sep 2 - Wed, Sep 30
YVR
Vancouver
MSN
Madison
CA $616 Roundtrip, found 6 days ago
CA $616
Roundtrip
found 6 days ago
Select WestJet flight, departing Wed, Sep 2 from Vancouver to Madison, returning Wed, Sep 30, priced at CA $616 found 6 days ago
Air Canada
Wed, Sep 9 - Tue, Sep 22
YVR
Vancouver
MSN
Madison
CA $617 Roundtrip, found 2 days ago
CA $617
Roundtrip
found 2 days ago
Select Air Canada flight, departing Wed, Sep 9 from Vancouver to Madison, returning Tue, Sep 22, priced at CA $617 found 2 days ago

Frequently asked questions

What is the name of Windsor's airport?
Organize 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 vacation, 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 vacation 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 organized 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 vacation 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

Expedia.ca gives you the best tools to secure great deals on flights to Windsor. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Windsor. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Windsor.

Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Windsor flights with full confidence knowing that you've found the best deal online.

Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Windsor.

Looking to save even more? Get additional savings by bundling your Windsor flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Windsor trip!

Travel information

Destination airport
Dane County Regional
Destination airport IATA code
MSN
Destination city name
Madison
Roundtrip price
CA $398

Trending flights to Windsor

Prices were available within the past 7 days and start at CA $260 for one-way flights and CA $399 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, Aug 14 - Wed, Aug 19
YHZ
Halifax
MSN
Madison
CA $473 Roundtrip, found 3 days ago
CA $473
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Aug 14 from Halifax to Madison, returning Wed, Aug 19, priced at CA $473 found 3 days ago

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