Title: Southwest Wisconsin Vacation Packages & Trips 2026 from CA $566 | Expedia.ca [Southwest Wisconsin Travel Guide](https://expedia.ca/Southwest-Wisconsin.dx6059824)[Hotels in Southwest Wisconsin](https://expedia.ca/Southwest-Wisconsin-Hotels.d6059824.Travel-Guide-Hotels)[Vacation Rentals in Southwest Wisconsin](https://expedia.ca/Southwest-Wisconsin-Vacation-Rentals.d6059824.Travel-Guide-VacationRentals)[Flights to Southwest Wisconsin](https://expedia.ca/Cheap-Flights-To-Southwest-Wisconsin.d6059824.Travel-Guide-Flights)[Southwest Wisconsin Car Rentals](https://expedia.ca/Car-Rentals-In-Southwest-Wisconsin.d6059824.Car-Rental-Guide) ![](https://images.trvl-media.com/place/5957/f96cbf4a-3a46-4cf7-b7f2-0fff893f2f53.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southwest Wisconsin Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Inbal Arieh - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ### Your Southwest Wisconsin Vacation Choose a vacation package to Southwest Wisconsin and make planning your adventure a breeze. With all the details arranged before you leave, you can focus on enjoying every second in this destination. A trip to Southwest Wisconsin wouldn't be complete without experiencing some of its best cities, starting with [Wisconsin Dells](https://www.expedia.ca/Wisconsin-Dells.d6059846.Destination-Travel-Guides). A couple of the most popular attractions here include Mt. Olympus Water and Theme Park and Chula Vista Waterparks. [La Crosse](https://www.expedia.ca/La-Crosse.d6023344.Destination-Travel-Guides) is another favourite city with Southwest Wisconsin travellers. Visitors to this destination enjoy Oktoberfest Grounds and Onalaska Omni Centre. From the moment you book your Southwest Wisconsin vacation to when you get back home, Expedia will take care of you every step of the way. ## Top Southwest Wisconsin Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Bridgeview Inn Chicago Area](https://images.trvl-media.com/lodging/92000000/91910000/91900800/91900710/6980505e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bridgeview Inn Chicago Area CA $566 per person Feb 13 - Feb 20 found 12 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 6.4/10 (105 reviews) Newly remodeled room. Reviewed on Oct 11, 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $993 per person Mar 19 - Mar 22 found 6 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again! Reviewed on Jan 3, 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $662 per person Mar 19 - Mar 22 found 6 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Everything is ok but no parking lot and too much fee Reviewed on Jan 6, 2026 ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $590 per person Mar 19 - Mar 22 found 6 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) Perfect location, comfortable and clean room Reviewed on Jan 5, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $708 per person Mar 19 - Mar 22 found 6 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Staff was friendly did amazing job with checking us in Reviewed on Dec 25, 2025 ## Where to stay in Southwest Wisconsin Find the best Southwest Wisconsin areas and neighborhoods for the activities you enjoy most. [Learn more about Southwest Wisconsin](https://expedia.ca/Southwest-Wisconsin.dx6059824) ![Madison featuring a house, a park and flowers](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/86000/86957-Madison.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Madison The ample dining options and fantastic lake views are top of the list for many visitors to Downtown Madison. A stop by Orpheum Theater or Overture Center for the Arts might round out your trip. [Find hotel + flight trips in Downtown Madison](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Madison&DestID=6059906&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://mediaim.expedia.com/destination/1/f80835acfc029051bd8d77dd7d1d420a.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Lake Delton 1 out of top 10 points of interest in this area If you're spending some time in Lake Delton, Noah's Ark Waterpark and Mt. Olympus Water and Theme Park are top sights worth seeing. [Find hotel + flight trips in Lake Delton](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Lake%20Delton&DestID=976030065785991168&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Monona Situated on Lake Monona's southeastern shore, this Madison suburb boasts the historic Indian Mounds Park, a site on the National Register of Historic Places. [Find hotel + flight trips in Monona](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Monona&DestID=134458&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Spring Brook While visiting Spring Brook, you might make a stop by sights like Spring Brook Golf Course and Lake Blass. [Find hotel + flight trips in Spring Brook](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Spring%20Brook&DestID=553248635976480150&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![La Crosse featuring a city and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/88000/88075-La-Crosse-And-Vicinity.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Historic Downtown La Crosse 1 out of top 10 points of interest in this area The abundant dining options and stunning river views are top of the list for many visitors to Historic Downtown La Crosse. A stop by La Crosse Center or Oktoberfest Grounds might round out your trip. [Find hotel + flight trips in Historic Downtown La Crosse](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Historic%20Downtown%20La%20Crosse&DestID=6179190&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Ready to book your vacation to Southwest Wisconsin? Choose your dates ## Southwest Wisconsin Hotel Deals ![The Madison Concourse Hotel and Governor's Club](https://images.trvl-media.com/lodging/1000000/30000/28500/28447/fb616a0c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Madison Concourse Hotel and Governor's Club 1 W Dayton St Madison WI Fully refundableReserve now, pay when you stay CA $173 CA $200 total Jan 18 - Jan 19 includes taxes & fees 9.4/10 Exceptional! (3,418 reviews) We were not aware we had a free breakfast. We did have a brunch on Christmas morning that was good, waiters were very nice. This is the second survey you have sent me. I replied to the first with comments about the lack of housekeeping for the entire stay. Had we not contacted the front desk we would ... Reviewed on Jan 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=18%2F01%2F2026&endDate=19%2F01%2F2026&selected=28447&PinnedHotelID=28447&HadPinnedHotel=true®ionId=6059824) ![DoubleTree by Hilton Madison East](https://images.trvl-media.com/lodging/1000000/10000/3200/3157/a90c37bb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Madison East 4402 E Washington Ave Madison WI Fully refundableReserve now, pay when you stay CA $146 CA $168 total Jan 25 - Jan 26 includes taxes & fees 9.2/10 Wonderful! (1,004 reviews) Friendly service at the front desk and bar/restaurant. Food was very good. Room was quiet and very clean. Great location close to MSN airport. Reviewed on Jan 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=3157&PinnedHotelID=3157&HadPinnedHotel=true®ionId=6059824) ![Hampton Inn & Suites Madison-West](https://images.trvl-media.com/lodging/3000000/2140000/2135000/2134982/w3835h2385x4y4-ff0bb2ca_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Madison-West 483 Commerce Dr Madison WI Fully refundableReserve now, pay when you stay CA $101 CA $116 total Jan 22 - Jan 23 includes taxes & fees 9/10 Wonderful! (1,011 reviews) The front dest staff were exceptional, always a smiling face and a welcoming greeting. The room was clean and comfortable. I am confused about the billing. I was charged, but also credited for more than the charge of the room. Reviewed on Jan 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F01%2F2026&endDate=23%2F01%2F2026&selected=2134982&PinnedHotelID=2134982&HadPinnedHotel=true®ionId=6059824) [See all 3,682 properties in Southwest Wisconsin](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F01%2F2026&endDate=09%2F01%2F2026®ionId=6059824) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Southwest Wisconsin ![Mt. Olympus Water and Theme Park](https://mediaim.expedia.com/destination/9/9394c7c0b9da275368306b266ca7e0ce.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Mt. Olympus Water and Theme Park Bring the kids to Mt. Olympus Water and Theme Park and have a fun-filled day at this amusement park in Wisconsin Dells. Stroll along the area's lakeside or experience its entertainment choices. [](https://expedia.ca/Mt-Olympus-Water-And-Theme-Park-Wisconsin-Dells.d6094033.Vacation-Attraction) #### Kalahari Indoor Waterpark Bring the family to Kalahari Indoor Waterpark and have a fun-filled day at this amusement park in Baraboo. Stroll along the lakeside or experience the entertainment choices in this family-friendly area. [](https://expedia.ca/Kalahari-Indoor-Waterpark-Baraboo.d6094031.Vacation-Attraction) #### Noah's Ark Waterpark Bring your family to Noah's Ark Waterpark and have a fun-filled day at this amusement park in Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices. [](https://expedia.ca/Noahs-Ark-Waterpark-Lake-Delton.d6094037.Vacation-Attraction) ## Frequently asked questions ### Can I cancel my flight booking to Southwest Wisconsin due to COVID-19? ### What's the best way to find cheap flights to Southwest Wisconsin that have flexible change policies? ### What are some of the general tips for travelers to Southwest Wisconsin during the COVID-19 outbreak? > - Investigate if any travel restrictions apply to your origin and destination before locking in a flight. Also check if there are any requirements you'll need to follow on arrival, such as taking a COVID-19 test. > - When you pass through airport screening, do not remove your face mask. You will be asked to lower it briefly for identification purposes. Travelers who refuse to wear a mask may face civil penalties and may also be escorted from the terminal. > - Rather than handing a TSA agent your boarding pass, position it directly on the scanner yourself. Once that's done, hold it up for inspection. > - One container of liquid hand sanitizer is now allowed in your carry-on bag. It must be no larger than 12 oz (350 ml), and you'll need to take it out of your bag at the X-ray machine for scanning. > - To minimize handling during the screening process, put items such as your belt, phone and wallet into your carry-on instead of into the bins. > - Transport all food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on makes it less likely that a TSA agent will need to touch and open your bag for inspection. ### Which airlines fly to Southwest Wisconsin? ### How can I find cheap tickets to Southwest Wisconsin? ### How much is a flight to Southwest Wisconsin? ### What are the most popular airports to fly into in Southwest Wisconsin? ### When is the cheapest time to fly to Southwest Wisconsin? ### How much is a plane ticket to Southwest Wisconsin? ### Which airlines with flights to Southwest Wisconsin employ COVID-19 cleanliness policies? > - Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant. > - American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant. > - United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [4 Star Hotels in Reedsburg ](https://www.expedia.ca/4Star-Reedsburg-Hotels.s40-0-d9466.Travel-Guide-Filter-Hotels) - 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Olympus Water and Theme Park ](https://www.expedia.ca/Mt-Olympus-Water-And-Theme-Park-Wisconsin-Dells.d6094033.Vacation-Attraction) - [Visit Muscoda ](https://www.expedia.ca/Muscoda.dx3000461893) - [New Lisbon Vacations ](https://www.expedia.ca/New-Lisbon.d181412.Destination-Travel-Guides) - [Noah's Ark Waterpark ](https://www.expedia.ca/Noahs-Ark-Waterpark-Wisconsin-Dells.d6094037.Vacation-Attraction) - [Olin Park ](https://www.expedia.ca/Olin-Park-Madison.d6292824.Vacation-Attraction) - [Paul Bunyan's Northwoods Lumberjack Show ](https://www.expedia.ca/Paul-Bunyans-Northwoods-Lumberjack-Show-Wisconsin-Dells.d6329236.Vacation-Attraction) - [Pirate's Cove Adventure Golf ](https://www.expedia.ca/Pirates-Cove-Adventure-Golf-Wisconsin-Dells.d6094039.Vacation-Attraction) - [Platteville Vacations ](https://www.expedia.ca/Platteville.d9130.Destination-Travel-Guides) - [Prairie Du Chien Vacations ](https://www.expedia.ca/Prairie-Du-Chien.d9368.Destination-Travel-Guides) - [Visit Richland Center ](https://www.expedia.ca/Richland-Center.dx181163) - [Visit Sextonville ](https://www.expedia.ca/Sextonville.dx771631968027873280) - [South Madison Vacations ](https://www.expedia.ca/South-Madison.d6059908.Destination-Travel-Guides) - [Timber Falls Adventure Park ](https://www.expedia.ca/Timber-Falls-Adventure-Park-Wisconsin-Dells.d6157680.Vacation-Attraction) - [Top Secret ](https://www.expedia.ca/Top-Secret-Wisconsin-Dells.d553248621558928139.Vacation-Attraction) - [Tower Hill State Park ](https://www.expedia.ca/Tower-Hill-State-Park-Spring-Green.d553248621561207065.Vacation-Attraction) - [Verona Vacations ](https://www.expedia.ca/Verona.d178206.Destination-Travel-Guides) - [Windsor Vacations ](https://www.expedia.ca/Windsor.d180667.Destination-Travel-Guides) - [Wisconsin Dells Vacations ](https://www.expedia.ca/Wisconsin-Dells.d6059846.Destination-Travel-Guides) - [Wizard Quest ](https://www.expedia.ca/Wizard-Quest-Wisconsin-Dells.d6094051.Vacation-Attraction) - [Woodside Wisconsin Dells Center Dome ](https://www.expedia.ca/Woodside-Wisconsin-Dells-Center-Dome-Wisconsin-Dells.d553248627444927838.Vacation-Attraction) - [Enterprise Rental Cars in Richland Center ](https://www.expedia.ca/Enterprise-Car-Rentals-In-Richland-Center.d181163-c15.Car-Rental-Guide-Suppliers) \* Savings based on package bookings compared to the price of the same components booked separately. 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