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Windsor

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Windsor Flights as Low as $162

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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 September, 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 13 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 $162, 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 $162 right now, why wait?

Windsor Flight Information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Roundtrip price
$162

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! (1,005 reviews)
"Clean and comfortable room, not great halls. Breakfast was very sad, had to get food elsewhere. Convenient location to freeway. Easy check in. Plenty of parking."

Reviewed on Jun 5, 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! (3,840 reviews)
"Great location and value! Room was surprisingly quiet given some construction works in the area and being across from the elevators. Long hallway in the room from the door to the living area helps. AC worked great."

Reviewed on Jun 5, 2026

The Madison Concourse Hotel and Governor's Club
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! (1,021 reviews)
"Excellent staff very clean well maintained property. Had an excellent stay"

Reviewed on Jun 5, 2026

DoubleTree by Hilton Madison East
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! (1,292 reviews)
"Room was very clean without an overwhelming air freshener smell. Bed very comfortable. Breakfast was very good and made fresh. Tables kept clean."

Reviewed on Jun 6, 2026

Baymont by Wyndham Madison West/Middleton WI West
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! (557 reviews)
"The M Club had good breakfast and snack items. The only downside was my room did not get cleaned one day"

Reviewed on Jun 4, 2026

Madison Marriott South
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! (1,024 reviews)
"Clean room and good breakfast options."

Reviewed on Jun 5, 2026

Tru by Hilton Madison West, WI
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! (1,001 reviews)
"I was in the company of a disabled elderly man. The motel staff was outstandingly kind and helpful to me and to him."

Reviewed on Jun 5, 2026

Best Western Plus InnTowner Madison
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! (1,004 reviews)
"It’s all around amazing!!!"

Reviewed on Jun 4, 2026

The Edgewater
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.