Cheap Flight Deals to Southwest Wisconsin WI from CA $373

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How to find cheap flights to Southwest Wisconsin?

The cheapest prices found with in the last 7 days for return flights were CA $640 and CA $373 for one-way flights to Southwest Wisconsin for the period specified. Prices and availability are subject to change. Additional terms apply

Mon, Oct. 6 - Tue, Oct. 21
YYJ
Victoria Intl.
MSN
Dane County Regional
CA $723 Roundtrip, found 1 day ago
CA $723
Roundtrip
found 1 day ago
Select WestJet flight, departing Mon, Oct. 6 from Victoria Intl. to Dane County Regional, returning Tue, Oct. 21, priced at CA $723 found 1 day ago
OriginDestinationTravel datesFlights from*
SEAMadisonOctober 9 to October 12CA $640
*Prices include taxes and fees

Your guide to flights to Southwest Wisconsin, WI

American Airlines, WestJet fly to Southwest Wisconsin, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Southwest Wisconsin WI currently costs between CA $640 and CA $723. Prices vary, but for the best fares, travel in September when prices are at their lowest.  

Top tips for finding cheap flights to Southwest Wisconsin  

The cheapest flight for a round trip to Southwest Wisconsin is currently CA $640. When you search for flights to Southwest Wisconsin, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Southwest Wisconsin for nearby days.  The cheapest month to travel to Southwest Wisconsin is October from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Southwest Wisconsin 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Southwest Wisconsin with Travelocity 

We have top deals on plane tickets even for last minute flights to Southwest Wisconsin, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Southwest Wisconsin for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Southwest Wisconsin

Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI
The price is CA $28 per night from Aug 17 to Aug 18
CA $28
per night
Aug 17 - Aug 18
Stay at this 3-star family-friendly resort in Wisconsin Dells. Enjoy an outdoor pool, free water park access, and parking (surcharge). Our guests praise the ...
6.8/10 (2,259 reviews)
"Family had a great time."

Reviewed on Aug. 2, 2025

Mt. Olympus Water & Theme Park Resort
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd, Madison, WI
The price is CA $65 per night from Aug 10 to Aug 11
CA $65
per night
Aug 10 - Aug 11
Stay at this motel in Madison. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.6/10 (1,005 reviews)
"2nd level hallway smelled of marijuana and my room smell of cigarette smoke."

Reviewed on Jul. 26, 2025

Motel 6 Madison, WI - East
Econo Lodge Madison East

Econo Lodge Madison East

2 out of 5
4726 E Washington Ave, Madison, WI
The price is CA $81 per night from Aug 5 to Aug 6
CA $81
per night
Aug 5 - Aug 6
Stay at this hotel in Madison. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.2/10 Good! (1,006 reviews)
"Friendly staff Loved the bed pullows"

Reviewed on Aug. 2, 2025

Econo Lodge Madison East
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Red Roof Inn Madison, WI

Red Roof Inn Madison, WI

2 out of 5
4830 Hayes Road, Madison, WI
The price is CA $89 per night from Aug 7 to Aug 8
CA $89
per night
Aug 7 - Aug 8
Stay at this hotel in Madison. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions East Towne Mall and Token Creek Park are located ...
5.6/10 (1,001 reviews)
"Ok but only 1 towel for 2 people"

Reviewed on Jul. 25, 2025

Red Roof Inn Madison, WI
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.

Our Top Southwest Wisconsin hotel with Airport Shuttles

Best Western East Towne Suites

Best Western East Towne Suites

2.5 out of 5
4801 Annamark Dr, Madison, WI
The price is CA $129 per night from Aug 6 to Aug 7
CA $129
per night
Aug 6 - Aug 7
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8/10 Very Good! (1,002 reviews)
"The property was very clean, the staff were friendly and helpful. A lot of places to eat near the hotel."

Reviewed on Aug. 2, 2025

Best Western East Towne Suites
AmericInn by Wyndham La Crosse Riverfront-Conference Center

AmericInn by Wyndham La Crosse Riverfront-Conference Center

2.5 out of 5
1835 Rose Street, La Crosse, WI
The price is CA $98 per night from Aug 24 to Aug 25
CA $98
per night
Aug 24 - Aug 25
Book a stay at this beach hotel in La Crosse. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the bar in our reviews. Popular ...
7.4/10 Good! (1,003 reviews)
"Great for kids. Pool area is very good"

Reviewed on Jul. 31, 2025

AmericInn by Wyndham La Crosse Riverfront-Conference Center
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
The price is CA $94 per night from Sep 1 to Sep 2
CA $94
per night
Sep 1 - Sep 2
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 ...
7.8/10 Good! (1,010 reviews)
"Wonderful"

Reviewed on Aug. 2, 2025

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

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue, Madison, WI
The price is CA $174 per night from Aug 31 to Sep 1
CA $174
per night
Aug 31 - Sep 1
Stay at this 3-star hotel in Madison. Enjoy free breakfast, free parking, and a free area shuttle. Our guests praise the breakfast and the helpful staff in our ...
9/10 Wonderful! (1,003 reviews)
"It's close to the college campus and has car service within 2 miles, which is great."

Reviewed on Aug. 1, 2025

Best Western Plus InnTowner Madison
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.

Luxury Hotels in Southwest Wisconsin

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
Stay at this 3.5-star 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! (2,917 reviews)
Beautiful Hotel
"This hotel is really beautiful, comfortable and clean. Great location in downtown Madison. The staff were top notch! Had drinks in the bar--friendly, chic atmosphere. I have nothing negative to say except that I was lucky that this was not a longer stay so I didn't have to wash my hair. The shower ..."

Reviewed on Aug. 1, 2025

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The Madison Concourse Hotel and Governor's Club
The Edgewater

The Edgewater

4.5 out of 5
1001 Wisconsin Place, Madison, WI
The price is CA $284 per night from Aug 10 to Aug 11
CA $284
per night
Aug 10 - Aug 11
Stay at this 4.5-star 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)
"Sunset view"

Reviewed on Jul. 31, 2025

The Edgewater
Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI
The price is CA $28 per night from Aug 17 to Aug 18
CA $28
per night
Aug 17 - Aug 18
Stay at this 3-star family-friendly resort in Wisconsin Dells. Enjoy an outdoor pool, free water park access, and parking (surcharge). Our guests praise the ...
6.8/10 (2,259 reviews)
"Family had a great time."

Reviewed on Aug. 2, 2025

Mt. Olympus Water & Theme Park Resort
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Best Western Premier Park Hotel

Best Western Premier Park Hotel

3.5 out of 5
22 S Carroll Street, Madison, WI
The price is CA $141 per night from Aug 10 to Aug 11
CA $141
per night
Aug 10 - Aug 11
Stay at this 3.5-star spa hotel in Madison. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (1,002 reviews)
Great staff, great location
"We loved our stay in Madison at the Best Western Premier Park. The staff at reception was very welcoming, friendly, and helpful. Our room was clean and spacious. We used the parking garage and the attendants were quick to get our car when we needed to leave for dinner. The location can't be beat ..."

Reviewed on Jul. 29, 2025

Best Western Premier Park Hotel
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.

Family Friendly Hotels in Southwest Wisconsin

Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI
The price is CA $28 per night from Aug 17 to Aug 18
CA $28
per night
Aug 17 - Aug 18
Stay at this 3-star family-friendly resort in Wisconsin Dells. Enjoy an outdoor pool, free water park access, and parking (surcharge). Our guests praise the ...
6.8/10 (2,259 reviews)
"Family had a great time."

Reviewed on Aug. 2, 2025

Mt. Olympus Water & Theme Park Resort
Chula Vista Resort, Trademark Collection by Wyndham

Chula Vista Resort, Trademark Collection by Wyndham

3.5 out of 5
2501 River Rd, PO Box 30, Wisconsin Dells, WI
The price is CA $139 per night from Sep 1 to Sep 2
CA $139
per night
Sep 1 - Sep 2
Stay at this 3.5-star spa resort in Wisconsin Dells. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Mt. Olympus Water and Theme ...
6.8/10 (1,000 reviews)
"Would be helpful to purchase new and improved mattresses. Our room had a sink that needs liquid plumber. The cover on the outside air conditioner unit is broken and pieces on the balcony is a bad look. Overall a great stay. Would highly recommend this resort. Staff very nice and helpful.😃"

Reviewed on Jul. 30, 2025

Chula Vista Resort, Trademark Collection by Wyndham
Tamarack Wisconsin Dells a Ramada by Wyndham

Tamarack Wisconsin Dells a Ramada by Wyndham

3 out of 5
874 Xanadu Rd., Wisconsin Dells, WI
Stay at this 3-star family-friendly vacation home in Wisconsin Dells. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff ...
9/10 Wonderful! (961 reviews)
"Loved it"

Reviewed on Jul. 28, 2025

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Tamarack Wisconsin Dells a Ramada by Wyndham
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Best Western Ambassador Inn & Suites

Best Western Ambassador Inn & Suites

2.5 out of 5
610 S Frontage Road, Wisconsin Dells, WI
The price is CA $107 per night from Sep 1 to Sep 2
CA $107
per night
Sep 1 - Sep 2
Stay at this hotel in Wisconsin Dells. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (1,007 reviews)
"Only stayed for one night, but was made to feel at home!"

Reviewed on Aug. 3, 2025

Best Western Ambassador Inn & Suites
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.

Best Southwest Wisconsin Flight and Hotel Packages

Southwest Wisconsin flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
per person
Sep 5 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
per person
Sep 19 - Sep 22
found 24 hours ago
Roundtrip flight included
Winnipeg (YWG) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
Don't see what you're looking for?
See all available trips from Toronto to Southwest Wisconsin
View all trips

Southwest Wisconsin flight + hotel packages - business class flights

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
per person
Sep 26 - Sep 29
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
per person
Sep 26 - Sep 29
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
per person
Sep 26 - Sep 29
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Don't see what you're looking for?
See all available trips from Toronto to Southwest Wisconsin
View all trips

Need a car after flight to Southwest Wisconsin?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

How much is the cheapest flight to Southwest Wisconsin?
For an idea of prices, the cheapest roundtrip flight to Southwest Wisconsin cost CA $640 during the last seven days. An excellent way to snap up a travel bargain is to be flexible with your dates. This price was available on Travelocity for flights to Southwest Wisconsin departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Southwest Wisconsin?
For your biggest chance at scoring a superb flight deal, time your break sometime during October. According to Travelocity's direct flight demand from January to December last year, it's the cheapest period to hop on a plane to Southwest Wisconsin.
How can I check my flight status to Southwest Wisconsin?
Get helpful alerts about your flight status and gate numbers with Trips. This convenient portal can be found at the top right of our homepage and is the place to view and manage your bookings. Sign in to your account in seconds and everything will be at your fingertips. You can also use the Travelocity app to see the details of your flight to Southwest Wisconsin while you're out and about — and even while you're offline. Travelocity's app can handle all your booking needs. Whether you want to organize transportation to or from the airport or share itinerary details with any members of your family flying with you, our intuitive app can help.
How do I find the best deals on flights to Southwest Wisconsin?
Be flexible with your travel dates and you might just find a deal you can't pass up. When searching for flights on Travelocity, click the "Flexible dates" option above your results to compare prices with surrounding days. Also try to book ahead of schedule and avoid vacation periods. In the last seven days, the best price for a return flight to Southwest Wisconsin was CA $640. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Southwest Wisconsin with Travelocity?
From cheap flights to Southwest Wisconsin to vacation packages, Travelocity is your one-stop shop for exciting adventures. With everything at hand, you can spend more time preparing for the fun things you'll be doing in Southwest Wisconsin and less time working on travel planning. Plus with our Price Match Guarantee and 24/7 customer assistance, our goal is to make your next vacation a hassle-free one.
What are the most popular flight routes to Southwest Wisconsin?
Check out these main flight routes to Southwest Wisconsin and start organizing your next adventure:

  • Chicago, IL (ORD-O'Hare Intl.) to Dane County Regional Airport (MSN) - 1,365 flights a month.
  • Minneapolis, MN (MSP-Minneapolis - St. Paul Intl.) to Dane County Regional Airport (MSN) - 1,005 flights a month.
  • Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Dane County Regional Airport (MSN) - 931 flights a month.

How much is a flight to Southwest Wisconsin on average?
Based on prices found on Travelocity over the last seven days, roundtrip flights to Southwest Wisconsin cost between CA $640 and CA $723. Whenever you're ready to go, Travelocity will help you find a fare that'll work with your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Plane Tickets To Southwest Wisconsin

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Southwest Wisconsin. Browse through our inventory to explore a wide range of cheap flights to Southwest Wisconsin to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Southwest Wisconsin as you anxiously await to exit the plane and explore what Southwest Wisconsin has to offer. Considering all the amazing local food and culture in Southwest Wisconsin, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Southwest Wisconsin to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Southwest Wisconsin without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Southwest Wisconsin with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Southwest Wisconsin today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.