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 $164

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

Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Bargain Flight
Frontier Airlines
Frontier Airlines
United
American Airlines
Delta
Frontier Airlines
Delta
United
Bargain Flight
Delta
Alaska Airlines

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 May, 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 14 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 $164, 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 $164 right now, why wait?

Windsor Flight Information
Destination airport
Dane County Regional
Destination airport IATA code
MSN
Roundtrip price
$164

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! (1,002 reviews)
If you want to buy drugs or listen to people fix their broken car right outside your window, then this is your kind of place. First room they put me in smelled of smoke so bad I thought the person was standing next to me and blowing smoke in my face. The second still smelled but I was stuck at that ...

Reviewed on Apr 26, 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! (3,678 reviews)
Staff was friendly but our shower door was really loose and starting to fall off, fridge never got cold

Reviewed on Apr 26, 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! (1,007 reviews)
Service was terrible

Reviewed on Apr 26, 2026

DoubleTree by Hilton Madison East
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! (1,002 reviews)
Great hotel

Reviewed on Apr 21, 2026

Best Western Plus InnTowner Madison
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! (1,008 reviews)
Great place for families! Lounge area has all the things for teens!

Reviewed on Apr 25, 2026

Tru by Hilton Madison West, WI
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! (1,005 reviews)
Breakfast was good and ready on time.

Reviewed on Apr 26, 2026

Hampton Inn & Suites Madison-West
Best Western Premier Park Hotel

Best Western Premier Park Hotel

4 out of 5
22 S Carroll Street Madison WI
Book a stay at this spa hotel in Madison. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (1,002 reviews)
Excellent location-walk to all the places downtown. Bed was comfortable!

Reviewed on Apr 24, 2026

Best Western Premier Park Hotel
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 ...
9.6/10 Exceptional! (1,004 reviews)
Spectacular!

Reviewed on Apr 25, 2026

DoubleTree by Hilton Madison Downtown
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.