Cheap Flight Deals to Southwest Wisconsin WI from CA $361

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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 $438 and CA $361 for one-way flights to Southwest Wisconsin for the period specified. Prices and availability are subject to change. Additional terms apply

Wed, Nov 12 - Sun, Nov 16
YYZ
Pearson Intl.
MSN
Dane County Regional
CA $629 Roundtrip, found 5 days ago
CA $629
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Nov 12 from Pearson Intl. to Dane County Regional, returning Sun, Nov 16, priced at CA $629 found 5 days ago
OriginDestinationTravel datesFlights from*
LAXMadisonOctober 30 to November 2CA $438
SEAMadisonOctober 31 to November 2CA $587
*Prices include taxes and fees

Your guide to flights to Southwest Wisconsin, WI

WestJet, American Airlines fly to Southwest Wisconsin, so use Travelocity to search, find, and compare some truly tempting deals from the 3 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 $438 and CA $629. Prices vary, but for the best fares, travel in October 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 $438. 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 November 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 $76 per night from Sep 24 to Sep 25
CA $76
CA $85 total
Sep 24 - Sep 25
includes taxes & fees
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 (2,419 reviews)
"Very good stay I loved it."

Reviewed on Sep 15, 2025

Opens in a new windowMt. 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 Sep 23 to Sep 24
CA $65
CA $76 total
Sep 23 - Sep 24
includes taxes & fees
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 (1,008 reviews)
Trip to see Weird Al.
"It is a nice place to stay. Tge staff and everyone we met there was very friendly. The room was clean and roomy, except for the bathroom. You really had no space for a bigger person like me to change in since I was traveling with my adult son for a concert. The beds were nice once you got in them, ..."

Reviewed on Sep 13, 2025

Opens in a new windowMotel 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 Sep 23 to Sep 24
CA $81
CA $94 total
Sep 23 - Sep 24
includes taxes & fees
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! (1,008 reviews)
"Curtain was falling off on one side. Broken. Need more fixing and maintenance. Not bad though. They had one clerk for check in for Morgan Wallen concert. They were not prepared for that. It took over an hour to check in, no early, or pre check in. Needed more staff. Messed up my pre game plans. Vending ..."

Reviewed on Sep 10, 2025

Opens in a new windowEcono 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 $88 per night from Sep 23 to Sep 24
CA $88
CA $101 total
Sep 23 - Sep 24
includes taxes & fees
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)
"Nice hotel. Clean and comfy. Also Nice staff. Felt welcomed when checking in"

Reviewed on Sep 12, 2025

Opens in a new windowRed 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 Sep 25 to Sep 26
CA $129
CA $149 total
Sep 25 - Sep 26
includes taxes & fees
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! (1,006 reviews)
"Great Coffee"

Reviewed on Sep 17, 2025

Opens in a new windowBest 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 $128 per night from Oct 5 to Oct 6
CA $128
CA $147 total
Oct 5 - Oct 6
includes taxes & fees
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! (1,006 reviews)
"Hotel was great and staff was very helpful and friendly. But, the bar at the hotel was under staffed! The waitresses did an excellent job but the bartender should have had help. And she wasn’t very good at her job. Other than that, excellent stay."

Reviewed on Sep 16, 2025

Opens in a new windowAmericInn 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 $100 per night from Oct 5 to Oct 6
CA $100
CA $115 total
Oct 5 - Oct 6
includes taxes & fees
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! (1,011 reviews)
"Quiet & convenient location"

Reviewed on Sep 16, 2025

Opens in a new windowBaymont 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 $198 per night from Oct 5 to Oct 6
CA $198
CA $229 total
Oct 5 - Oct 6
includes taxes & fees
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! (1,009 reviews)
A great stay in Madison.
"Everything was updated, comfortable and clean. The staff from the front desk to the breakfast crew were the best and so friendly. The location was perfect for enjoying the campus and downtown. Even a few blocks from an easy to use bus stop."

Reviewed on Sep 15, 2025

Opens in a new windowBest 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! (3,093 reviews)
Definite yes!
"Wonderful. Highly recommend."

Reviewed on Sep 16, 2025

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Opens in a new windowThe 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 $309 per night from Oct 19 to Oct 20
CA $309
CA $392 total
Oct 19 - Oct 20
includes taxes & fees
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! (1,003 reviews)
"Just loved the lake view from our room"

Reviewed on Sep 2, 2025

Opens in a new windowThe 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 $76 per night from Sep 24 to Sep 25
CA $76
CA $85 total
Sep 24 - Sep 25
includes taxes & fees
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 (2,419 reviews)
"Very good stay I loved it."

Reviewed on Sep 15, 2025

Opens in a new windowMt. Olympus Water & Theme Park Resort
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Best Western Premier Park Hotel

Best Western Premier Park Hotel

4 out of 5
22 S Carroll Street, Madison, WI
The price is CA $141 per night from Oct 5 to Oct 6
CA $141
CA $163 total
Oct 5 - Oct 6
includes taxes & fees
Stay at this 4-star spa hotel in Madison. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,011 reviews)
"Overall the hotel was very good experience. Our only issue was in the restaurant. When we checked in on Friday afternoon we decided to have dinner in the hotel restaurant. Even though we had a party of nine, it should not have taken over an hour to get our food. Also, the server never came over to ..."

Reviewed on Sep 15, 2025

Opens in a new windowBest 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 $76 per night from Sep 24 to Sep 25
CA $76
CA $85 total
Sep 24 - Sep 25
includes taxes & fees
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 (2,419 reviews)
"Very good stay I loved it."

Reviewed on Sep 15, 2025

Opens in a new windowMt. 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
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 (1,007 reviews)
"Nice stay we always go to Wilderness but this place is in a beautiful spot arround the river for families nice very clean rooms and area staff very friendly the breakfast but was super delicious the waitress Erica make our morning very nice and friendly I’ll really recommend Chula Vista"

Reviewed on Sep 13, 2025

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Opens in a new windowChula 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! (968 reviews)
"Great place to stay"

Reviewed on Sep 3, 2025

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Opens in a new windowTamarack 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 $92 per night from Sep 23 to Sep 24
CA $92
CA $104 total
Sep 23 - Sep 24
includes taxes & fees
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! (1,027 reviews)
"Everything was great . The only thing I didn’t like was that the breakfast end at 9:30am"

Reviewed on Sep 14, 2025

Opens in a new windowBest 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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Price was CA $1,018, price is now CA $662 per person
CA $662
per person
Nov 10 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Price was CA $1,200, price is now CA $735 per person
CA $735
per person
Nov 10 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Price was CA $2,909, price is now CA $1,845 per person
CA $1,845
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Don't see what you're looking for?
See all available trips from Edmonton 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 $438 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 November. 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 $438. 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 $438 and CA $629. 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.