Title: Southern Wisconsin Vacation Packages & Trips 2026 from CA $565 | Expedia.ca [Southern Wisconsin Travel Guide](https://expedia.ca/Southern-Wisconsin.dx553248635975749457)[Hotels in Southern Wisconsin](https://expedia.ca/Southern-Wisconsin-Hotels.d553248635975749457.Travel-Guide-Hotels)[Vacation Rentals in Southern Wisconsin](https://expedia.ca/Southern-Wisconsin-Vacation-Rentals.d553248635975749457.Travel-Guide-VacationRentals)[Flights to Southern Wisconsin](https://expedia.ca/Cheap-Flights-To-Southern-Wisconsin.d553248635975749457.Travel-Guide-Flights)[Southern Wisconsin Car Rentals](https://expedia.ca/Car-Rentals-In-Southern-Wisconsin.d553248635975749457.Car-Rental-Guide) ![](https://images.trvl-media.com/place/2325/f29f5e3d-0eb0-45b8-94f1-06284f8af3d0.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southern Wisconsin Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Evae - ## 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 Southern Wisconsin Vacation Our Southern Wisconsin vacation packages provide an easy, affordable and immersive way to experience everything this incredible destination has to offer. If it's distilleries and craft breweries and dining you're after, this is the place to be. With so much to see and do on a trip to Southern Wisconsin, it can be hard to know where to begin. Kick off your journey in [Milwaukee](https://www.expedia.ca/Milwaukee.d602647.Destination-Travel-Guides) at American Family Field and Wisconsin State Fair Park — two much-loved attractions here. Another city worthy of a spot on your itinerary is [Wisconsin Dells](https://www.expedia.ca/Wisconsin-Dells.d6059846.Destination-Travel-Guides). Be sure not to miss Mt. Olympus Water and Theme Park and Chula Vista Waterparks. Expedia is a one-stop shop when it comes to organizing your Southern Wisconsin vacation. From hotels and flights, to car rentals and more, we know how to curate a travel experience like no other. ## Top Southern Wisconsin Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $565 per person Feb 13 - Feb 16 found 11 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in. Reviewed on Nov 25, 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 $900 per person Jan 21 - Jan 24 found 18 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted. Reviewed on Dec 11, 2025 ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $596 per person Feb 13 - Feb 16 found 11 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Kitchen and laundry in room, staff was very friendly and helpful. Reviewed on Dec 8, 2025 ![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 $1,070 per person Mar 6 - Mar 10 found 22 hours ago Roundtrip non-stop flight included Québec (YQB) to Chicago (ORD) 9/10 Wonderful! (380 reviews) The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7\. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience. Reviewed on Dec 9, 2025 ![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 $935 per person Mar 6 - Mar 10 found 22 hours ago Roundtrip non-stop flight included Québec (YQB) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff. Reviewed on Dec 8, 2025 ## Where to stay in Southern Wisconsin Find the best Southern Wisconsin areas and neighborhoods for the activities you enjoy most. [Learn more about Southern Wisconsin](https://expedia.ca/Southern-Wisconsin.dx553248635975749457) ![Milwaukee](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/219000/219557-Milwaukee.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Milwaukee Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system. [Find hotel + flight trips in Downtown Milwaukee](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Milwaukee&DestID=6059651&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![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) ![Milwaukee County Zoo which includes zoo animals and dangerous animals as well as a family](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/31000/31457-Milwaukee-County-Zoo.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Wauwatosa Wauwatosa is known for its abundant dining options, and you can plan a trip to Mayfair Mall and The Mayfair Collection while you're in town. [Find hotel + flight trips in Wauwatosa](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Wauwatosa&DestID=6059657&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) ### West Allis West Allis is noteworthy for its restaurants, and you can make a stop at top attractions like Milwaukee Mile Speedway and Wisconsin State Fair Park. [Find hotel + flight trips in West Allis](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=West%20Allis&DestID=7685&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Milwaukee Public Library which includes interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/31000/31500-Milwaukee-Public-Library.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Westown 1 out of top 10 points of interest in this area 4/5(8 area reviews) While visiting Westown, you might make a stop by sights like Miller High Life Theatre and UW–Milwaukee Panther Arena. [Find hotel + flight trips in Westown](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Westown&DestID=553248635976470851&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Ready to book your vacation to Southern Wisconsin? Choose your dates ## Southern Wisconsin Hotel Deals ![The Pfister Hotel](https://images.trvl-media.com/lodging/1000000/20000/19500/19467/169f18e6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Pfister Hotel 424 E Wisconsin Ave Milwaukee WI Fully refundableReserve now, pay when you stay CA $210 CA $248 total Jan 1 - Jan 2, 2026 includes taxes & fees 9.4/10 Exceptional! (1,800 reviews) Amazing, historic hotel in downtown Milwaukee! Reviewed on Dec 8, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%2F01%2F2026&selected=19467&PinnedHotelID=19467&HadPinnedHotel=true®ionId=553248635975749457) ![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 $185 CA $214 total Dec 19 - Dec 20 includes taxes & fees 9.4/10 Exceptional! (3,372 reviews) Everything was great! Reviewed on Dec 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F12%2F2025&endDate=20%2F12%2F2025&selected=28447&PinnedHotelID=28447&HadPinnedHotel=true®ionId=553248635975749457) ![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/63d91083_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Saint Kate - The Arts Hotel 139 E Kilbourn Ave Milwaukee WI Fully refundableReserve now, pay when you stay CA $179 CA $212 total Jan 4 - Jan 5, 2026 includes taxes & fees 9.6/10 Exceptional! (2,459 reviews) Always enjoy staying at St Kate’s. Clean, convenient, friendly, and good music. Reviewed on Dec 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=23253&PinnedHotelID=23253&HadPinnedHotel=true®ionId=553248635975749457) [See all 7,427 properties in Southern Wisconsin](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=553248635975749457) 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 Southern 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 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) ![Harley-Davidson Museum featuring interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54544-Harley-Davidson-Museum-Milwaukee.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Harley-Davidson Museum 5/5(13 reviews) Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours. [](https://expedia.ca/Harley-Davidson-Museum-Menomonee-River-Valley.d6279040.Vacation-Attraction) #### Kalahari Indoor Waterpark 4/5(1 review) Have a fun-filled day at Kalahari Indoor Waterpark and see why people love this amusement park in Baraboo. Stroll along the riverfront or experience the entertainment choices in this family-friendly area. [](https://expedia.ca/Kalahari-Indoor-Waterpark-Baraboo.d6094031.Vacation-Attraction) ## Frequently asked questions ### Can I cancel my flight booking to Southern Wisconsin due to COVID-19? ### What's the best way to find cheap flights to Southern Wisconsin that have flexible change policies? ### What are some of the general tips for travelers to Southern Wisconsin during the COVID-19 outbreak? > - Understand what, if any, restrictions or rules apply to both your origin and destination. You may not be able to travel depending on local circumstances, so check before you book your flight. > - Wear a face mask during airport screening. A TSA employee will ask you to temporarily lower your mask for ID purposes. > - Instead of handing a TSA employee your boarding pass, position it straight on the reader yourself. After that, hold it up for inspection. > - One container of liquid hand sanitizer is now permitted in your carry-on bag. It must not be larger than 12 oz (350 ml), and you'll have to remove it from your bag for X-ray screening. > - Put any personal items (like your phone, wallet and keys) in your carry-on rather than a bin to minimize handling during the screening process. > - Transport your food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on means it's less likely a TSA agent will need to open your bag for inspection. ### Which airlines fly to Southern Wisconsin? ### How can I find cheap tickets to Southern Wisconsin? ### How much is a flight to Southern Wisconsin? ### What are the most popular airports to fly into in Southern Wisconsin? ### When is the cheapest time to fly to Southern Wisconsin? ### How much is a plane ticket to Southern Wisconsin? ### Which airlines with flights to Southern Wisconsin employ COVID-19 cleanliness policies? > - Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant. > - 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. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - [Astico Hotels ](https://www.expedia.ca/Astico-Hotels.d553248635975847010.Travel-Guide-Hotels) - 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