Search Cheap Flights to
Windsor

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Windsor Flights as Low as $203

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Delta
Bargain Flight
Frontier Airlines
Bargain Flight
Frontier Airlines
Delta
American Airlines
Delta
Delta
Delta
Delta
Delta
Delta
Bargain Flight
Delta
Bargain Flight

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 March, 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 12 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 $203, 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 $203 right now, why wait?

Windsor Flight Information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Roundtrip price
$203

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 ...
7/10 Good! (1,002 reviews)
Staff was rude

Reviewed on Jan 2, 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! (3,462 reviews)
So I had initially attempted to book a three day stay and upon doing so I had a staff member interrupt me and stopped me and tell me that they didn’t have availability or reservation availability for Saturday and therefore she would have to charge me individually for the first night, which was Friday ...

Reviewed on Jan 20, 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 WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (1,141 reviews)
The room was clean and the pool area was excellent. Really like how the pool is warm. The breakfast was a good variety of foods.

Reviewed on Jan 19, 2026

Baymont by Wyndham Madison West/Middleton WI West
La Quinta Inn & Suites by Wyndham Madison American Center

La Quinta Inn & Suites by Wyndham Madison American Center

3 out of 5
5217 E Terrace Dr Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.2/10 Very Good! (1,406 reviews)
Room seemed clean, toilet ran all night needs parts, bed had pit in it you roll to center, I wish all hotels quit adding flour to scrambeld eggs and serve horrible sausage. Staff was great

Reviewed on Jan 19, 2026

La Quinta Inn & Suites by Wyndham Madison American Center
Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

2.5 out of 5
483 Commerce Dr 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 pool in our ...
9/10 Wonderful! (1,003 reviews)
The pillows were amazing! The bed was okay! The breakfast was tasty and it wasn’t the same everyday. The people were friendly and helpful! The hot tub is huge and nice and hot! It helped melt away the winter aches. There are lots of good shops nearby. We had fun!

Reviewed on Jan 9, 2026

Hampton Inn & Suites Madison-West
Hilton Garden Inn Madison Downtown

Hilton Garden Inn Madison Downtown

3 out of 5
770 Regent Street Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy breakfast (surcharge), a 24-hour fitness center, and parking (surcharge). Our guests praise the ...
9.2/10 Wonderful! (843 reviews)
Space was clean. Staff was friendly and welcoming.

Reviewed on Jan 16, 2026

Hilton Garden Inn Madison Downtown
DoubleTree by Hilton Madison Downtown

DoubleTree by Hilton Madison Downtown

4 out of 5
525 West Johnson Street Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
9.4/10 Exceptional! (1,001 reviews)
Very helpful friendly staff. Very clean room.

Reviewed on Jan 9, 2026

DoubleTree by Hilton Madison Downtown
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! (1,005 reviews)
The location the facilities the stuff all amazing !

Reviewed on Jan 16, 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.