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Windsor

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Windsor Flights as Low as $157

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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 MSN 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 August, 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 11 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 Dane County Regional 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 $157, 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 $157 right now, why wait?

Windsor Flight Information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Roundtrip price
$157

Last Minute Hotel Deals in Windsor

Days Inn by Wyndham Madison NE/Windsor

Days Inn by Wyndham Madison NE/Windsor

2 out of 5
6311 Rostad Dr Windsor WI
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,000 reviews)
"Place needs a major upgrade/ cleaning. Room had a serious urine smell issue-no doubt the result of the “”pet friendly “” policy. Overall, the place is worn-out. Actually quite expensive for what you get."

Reviewed on Jun 21, 2026

Days Inn by Wyndham Madison NE/Windsor
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool ...
9.4/10 Exceptional! (3,896 reviews)
"Second time in ten days we chose to stay and again it was the right choice all around!"

Reviewed on Jun 26, 2026

The Madison Concourse Hotel and Governor's Club
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr Madison WI
Book a stay at this family-friendly hotel in Madison. Enjoy free breakfast, free parking, and a free airport shuttle. Our guests praise the breakfast and the ...
8/10 Very Good! (1,329 reviews)
"3rd year in a row staying there... Not a Hyatt Regency--but great price and value... and their new Shower Heads are the BOMB... yowza"

Reviewed on Jun 27, 2026

Baymont by Wyndham Madison West/Middleton WI West
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a free area shuttle. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,003 reviews)
"Loved the breakfast"

Reviewed on Jun 26, 2026

Best Western Plus InnTowner Madison
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9.4/10 Exceptional! (1,020 reviews)
"Clean room and great staff"

Reviewed on Jun 26, 2026

DoubleTree by Hilton Madison East
Tru by Hilton Madison West, WI

Tru by Hilton Madison West, WI

2.5 out of 5
8102 Watts Rd. Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (1,007 reviews)
"Room was nice and clean . Staff was amazing and the breakfast was delicious."

Reviewed on Jun 27, 2026

Tru by Hilton Madison West, WI
The Edgewater

The Edgewater

4.5 out of 5
1001 Wisconsin Place Madison WI
Book a stay at this luxury hotel in Madison. Enjoy a full-service spa, 4 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9.2/10 Wonderful! (1,002 reviews)
"Nice stay with lake view dining"

Reviewed on Jun 24, 2026

The Edgewater
Madison Marriott South

Madison Marriott South

3.5 out of 5
706 John Nolen Dr Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
9/10 Wonderful! (569 reviews)
"We were just there for a Saturday night and enjoyed our stay. After a busy day, we enjoyed a few cocktails at the bar and the server was engaging (while busy) Bobcats off to her. A++ stay, thank you!"

Reviewed on Jun 15, 2026

Madison Marriott South
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.