Title: Southwest Wisconsin Vacation Packages & Trips 2026 from CAย $673 | 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. ![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Banque Hotel CA $673 per person Apr 22 - Apr 25 found 5 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.4/10 Exceptional! (447 reviews) Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring. Reviewed on Jan 26, 2026 ![Level Chicago โ€“ 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 โ€“ Old Town Downtown Chicago CA $930 per person Mar 21 - Mar 27 found 11 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9/10 Wonderful! (380 reviews) My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone! Reviewed on Feb 2, 2026 ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wade Downtown Chicago CA $1,178 per person Apr 27 - May 3 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 8.4/10 Very Good! (1,444 reviews) The view from my room was stunning Reviewed on Feb 7, 2026 ![JW Marriott Chicago](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/232aa080_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### JW Marriott Chicago Downtown Chicago CA $707 per person May 1 - May 3 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.2/10 Wonderful! (1,000 reviews) Bottle of waters were not stocked in the refrigerator. Reviewed on Jan 6, 2026 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $972 per person Mar 21 - Mar 27 found 11 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium. Reviewed on Jan 31, 2026 ## 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) ![Wisconsin State Capitol building, view from Monona Terrace rooftop.; Shutterstock ID 5305432](https://images.trvl-media.com/place/6059906/c1fb6a54-36b0-4697-a90e-8414843d0e93.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Madison 1 out of top 10 points of interest in this area 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://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.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) ![Moss and flowing water of the dells of the eau claire in Aniwa, Wisconsin](https://images.trvl-media.com/place/553248635976480150/93804384-e9fa-4762-904e-3bc124de453c.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) ![The International Friendship Gardens in La Crosse, WI offer beautiful blooms from various sister cities around the world. I love the German gardens. The gardens are near the convergence of three rivers; the Mighty Mississippi, Black River, and La Crosse River. ๐Ÿ˜Š๐ŸŒผ #flowers ](https://images.trvl-media.com/place/6023344/97a9d3ba-6d0f-4d0c-8d67-96ef94b62c58.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Historic Downtown La Crosse 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) ![Madison Skyline](https://images.trvl-media.com/place/134458/b1acd50c-da8b-4ea9-885b-5ff2bf6363a7.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) ## 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 9.4/10 Exceptional! (3,477 reviews) Great as always Reviewed on Feb 3, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=28447&PinnedHotelID=28447&HadPinnedHotel=true®ionId=6059824) [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=28447&PinnedHotelID=28447&HadPinnedHotel=true®ionId=6059824) ![Mt. Olympus Water & Theme Park Resort](https://images.trvl-media.com/lodging/10000000/9330000/9324500/9324429/a09e80be_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Mt. Olympus Water & Theme Park Resort 655 N. Frontage Road Wisconsin Dells WI Fully refundableReserve now, pay when you stay CA $68 CA $77 total Feb 9 - Feb 10 includes taxes & fees 6.8/10 (2,607 reviews) Not much staff around in the hotel area. Water park lots of staff/lifeguards. One section of water park was closed the 2nd day and Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=9324429&PinnedHotelID=9324429&HadPinnedHotel=true®ionId=6059824) ![Baymont by Wyndham Madison West/Middleton WI West](https://images.trvl-media.com/lodging/1000000/50000/40100/40004/75db6fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baymont by Wyndham Madison West/Middleton WI West 8102 Excelsior Dr Madison WI Fully refundableReserve now, pay when you stay CA $74 CA $85 total Feb 9 - Feb 10 includes taxes & fees 8/10 Very Good! (1,159 reviews) Great breakfast and all day coffee Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=40004&PinnedHotelID=40004&HadPinnedHotel=true®ionId=6059824) [See all 3,700 properties in Southwest Wisconsin](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%2F02%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 ![Slidewheel water at a water park. ](https://images.trvl-media.com/place/6094033/7e55149e-6e82-4adc-a8ea-ad783f467ac1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Mt. Olympus Water and Theme Park 5/5(3 reviews) 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 riverfront or experience its entertainment choices. [](https://expedia.ca/Mt-Olympus-Water-And-Theme-Park-Wisconsin-Dells.d6094033.Vacation-Attraction) ![Casino hotel and convention center by Upper Mississippi on calm misty morning at Dubuque Iowa](https://images.trvl-media.com/place/6106010/f5a97944-8518-4072-89b3-4ae659e2143b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Q Casino Why not roll the dice with a visit to Q Casino during your visit to Dubuque? Make time to visit the area's casinos, or simply enjoy its top-notch restaurants. [](https://expedia.ca/Q-Casino-Dubuque.d6106010.Vacation-Attraction) ![Summer road trip ๐Ÿš— to Lake Placid, a quaint village in the Adirondacks region (which hosted the 1980 Winter Olympics) โ›ท. In town for just a weekend, we decided to do the shortest and easiest hike in Adirondack and that was Cascade Mountain. โ›ฐ At an elevation of around 4000 ft., it offers great views of Lake Placid for a casual hiker. ๐Ÿ‘Ÿ๐Ÿ‘Ÿ Trip highlight: ๐ŸŒŒStargazing near a surreal mist covered pond in Tupper Lake area, with wolves ๐Ÿบ howling nearby.](https://images.trvl-media.com/place/6185919/1a36364e-4679-46b2-bde9-d4a851e0038d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cascade Mountain Ski Area Hit the slopes in Portage with a visit to Cascade Mountain Ski Area. Wander the lakeside or discover the area's waterfalls. [](https://expedia.ca/Cascade-Mountain-Ski-Area-Portage.d6185919.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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