Title: Southern Wisconsin Vacation Packages & Trips 2026 from CA $572 | 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. ![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 $572 per person Mar 17 - Mar 20 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back! Reviewed on Jan 11, 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 $1,032 per person Mar 17 - Mar 20 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Staff were impeccable.. greeted with small glass of champagne. Bed was comfortable, room was quiet. Would definitely stay here again.. Reviewed on Jan 11, 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 $742 per person Mar 17 - Mar 20 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay. Reviewed on Jan 12, 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 $713 per person Mar 17 - Mar 20 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on Jan 8, 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 $689 per person Mar 17 - Mar 20 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) Great location, clean hotel Reviewed on Jan 11, 2026 ## 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 $207 CA $244 total Jan 15 - Jan 16 includes taxes & fees 9.4/10 Exceptional! (1,864 reviews) This is a beautiful historic hotel with a number of wonderful amenities. Unfortunately, we had a few problems with food/drink orders being forgotten both in the Mason Street Grill and room service. The staff handled these situations well by providing free items in compensation. The hotel was also ... Reviewed on Jan 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F01%2F2026&endDate=16%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 $210 CA $248 total Jan 24 - Jan 25 includes taxes & fees 9.6/10 Exceptional! (2,516 reviews) Rooms are clean , valet parking is terrible. Many times I almost had to valet my car on my own ,because nobody was there to assist Reviewed on Jan 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F01%2F2026&endDate=25%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 9.4/10 Exceptional! (3,425 reviews) Staff was amazing. It was very clean and had all the amenities that we needed. Reviewed on Jan 6, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=27%2F01%2F2026&endDate=28%2F01%2F2026&selected=28447&PinnedHotelID=28447&HadPinnedHotel=true®ionId=553248635975749457) [](https://expedia.ca/Hotel-Search?startDate=27%2F01%2F2026&endDate=28%2F01%2F2026&selected=28447&PinnedHotelID=28447&HadPinnedHotel=true®ionId=553248635975749457) [See all 7,372 properties in Southern Wisconsin](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=14%2F01%2F2026&endDate=15%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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[Lake Ripley Park Beach ](https://www.expedia.ca/Lake-Ripley-Park-Beach-Cambridge.d6276951.Vacation-Attraction) - [Larson's Famous Clydesdales ](https://www.expedia.ca/Larsons-Famous-Clydesdales-Ripon.d553248621532659289.Vacation-Attraction) - [Madison Vacations ](https://www.expedia.ca/Madison.d602704.Destination-Travel-Guides) - [Mequon Vacations ](https://www.expedia.ca/Mequon.d8809.Destination-Travel-Guides) - [Montello Vacations ](https://www.expedia.ca/Montello.d3000008237.Destination-Travel-Guides) - [Olin Park ](https://www.expedia.ca/Olin-Park-Madison.d6292824.Vacation-Attraction) - [Oshkosh Vacations ](https://www.expedia.ca/Oshkosh.d2699.Destination-Travel-Guides) - [Pettit National Ice Center ](https://www.expedia.ca/Pettit-National-Ice-Center-Milwaukee.d6335062.Vacation-Attraction) - [Shalom Wildlife ](https://www.expedia.ca/Shalom-Wildlife-West-Bend.d6335542.Vacation-Attraction) - [South Madison Vacations ](https://www.expedia.ca/South-Madison.d6059908.Destination-Travel-Guides) - [Troll Beach ](https://www.expedia.ca/Troll-Beach-Stoughton.d553248621558012059.Vacation-Attraction) - [Verona Vacations ](https://www.expedia.ca/Verona.d178206.Destination-Travel-Guides) - [Washington County Fair Grounds ](https://www.expedia.ca/Washington-County-Fair-Grounds-West-Bend.d6181503.Vacation-Attraction) - [Whitewater Vacations ](https://www.expedia.ca/Whitewater.d7620.Destination-Travel-Guides) - [Windsor Vacations ](https://www.expedia.ca/Windsor.d180667.Destination-Travel-Guides) - [Wisconsin Vacations ](https://www.expedia.ca/Wisconsin.d251.Destination-Travel-Guides) - [Enterprise Rental Cars in Watertown ](https://www.expedia.ca/Enterprise-Car-Rentals-In-Watertown.d56036-c15.Car-Rental-Guide-Suppliers) - [Beaver Dam Vacation Rentals ](https://www.expedia.ca/Beaver-Dam-Vacation-Rentals.d6538.Travel-Guide-VacationRentals) - [Columbus Vacation Rentals ](https://www.expedia.ca/Columbus-Vacation-Rentals.d91635.Travel-Guide-VacationRentals) \* Savings based on package bookings compared to the price of the same components booked separately. 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