Title: Southern Wisconsin Vacation Packages & Trips 2026 from CA $456 | 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. ![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Orrington / Evanston Downtown Evanston CA $456 per person Feb 13 - Feb 16 found 20 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 7.6/10 Good! (1,002 reviews) yes, courteous and professional. Reviewed on Jan 3, 2026 ![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 $1,060 per person Feb 26 - Mar 1 found 11 hours ago Roundtrip non-stop flight included Hamilton (YHM) 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 ![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 $866 per person Mar 10 - Mar 14 found 16 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) The experience of the hotel was amazing Reviewed on Jan 6, 2026 ![Holiday Inn Express Milwaukee Downtown by IHG](https://images.trvl-media.com/lodging/58000000/57140000/57132500/57132464/ecb2f8b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Milwaukee Downtown by IHG Downtown Milwaukee CA $1,435 per person Mar 24 - Mar 30 found 3 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Milwaukee (MKE) 9/10 Wonderful! (1,002 reviews) The cleanness of the room, the staff accessibility to everything that was a very nice stay. Reviewed on Jan 1, 2026 ![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Virgin Hotels Chicago Downtown Chicago CA $899 per person Mar 15 - Mar 20 found 1 hour ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,404 reviews) Room was great, staff was incredible and so friendly! Location was awesome-restaurant was closed during our stay so -1 Star but would recommend. Reviewed on Dec 21, 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 Milwaukee Public Museum. [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 $179 CA $211 total Jan 27 - Jan 28 includes taxes & fees 9.4/10 Exceptional! (1,854 reviews) Yes Reviewed on Jan 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=27%2F01%2F2026&endDate=28%2F01%2F2026&selected=19467&PinnedHotelID=19467&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 $214 CA $253 total Jan 14 - Jan 15 includes taxes & fees 9.6/10 Exceptional! (2,520 reviews) Great staff, amenities and room. Everything was clean and professional Reviewed on Jan 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=14%2F01%2F2026&endDate=15%2F01%2F2026&selected=23253&PinnedHotelID=23253&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 $198 CA $229 total Jan 10 - Jan 11 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=10%2F01%2F2026&endDate=11%2F01%2F2026&selected=28447&PinnedHotelID=28447&HadPinnedHotel=true®ionId=553248635975749457) [See all 7,375 properties in Southern Wisconsin](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F01%2F2026&endDate=10%2F01%2F2026®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 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) ![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 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 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) ## 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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