Title: Romantic Vacations in Southern Wisconsin 2026 | Expedia.ca ![](https://images.trvl-media.com/place/2325/f29f5e3d-0eb0-45b8-94f1-06284f8af3d0.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southern Wisconsin Romantic Vacations ## 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 ## Flight and Romantic hotel deals in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Swissotel - Chicago Downtown Chicago CA $413 per person Feb 1 - Feb 3 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (3,023 reviews) Wonderful. It’s just an overnight stay but the staff is exceptional Reviewed on Dec 19, 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 $1,262 per person Mar 15 - Mar 19 found 11 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) From staff to room it was a amazing experience. Reviewed on Dec 18, 2025 ![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 $741 per person Mar 15 - Mar 19 found 10 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Clean and quiet room. Staff was ver helpful. Breakfast buffet was amazing! Only beef we had was that the room temperature was too hot!! Temp was 77degrees was only able to get down to 74\. Maintenance did bring us a fan. They could save on the heating bill by adjusting the furnace. Reviewed on Dec 18, 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 $606 per person Feb 13 - Feb 16 found 4 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (401 reviews) Great location, clean room and friendly staff! Reviewed on Dec 14, 2025 ![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 $591 per person Mar 16 - Mar 19 found 24 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 7.6/10 Good! (1,002 reviews) Clean room, good service and great area. Reviewed on Dec 18, 2025 Don't see what you're looking for? See all available trips from Columbus to Southern Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic holidays in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,079 per person Feb 25 - Feb 28 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,007 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on Dec 16, 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 $1,262 per person Mar 15 - Mar 19 found 11 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) From staff to room it was a amazing experience. Reviewed on Dec 18, 2025 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,820 per person Mar 15 - Mar 19 found 10 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Absolutely fantastic hotel great service, you couldn’t ask for more. Reviewed on Dec 3, 2025 Don't see what you're looking for? See all available trips from Columbus to Southern Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Romantic holidays in Southern Wisconsin 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 $524 per person Jan 21 - Jan 24 found 24 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Clean and quiet room. Staff was ver helpful. Breakfast buffet was amazing! Only beef we had was that the room temperature was too hot!! Temp was 77degrees was only able to get down to 74\. Maintenance did bring us a fan. They could save on the heating bill by adjusting the furnace. Reviewed on Dec 18, 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 $1,017 per person Jan 21 - Jan 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) From staff to room it was a amazing experience. Reviewed on Dec 18, 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 $606 per person Feb 13 - Feb 16 found 4 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (401 reviews) Great location, clean room and friendly staff! Reviewed on Dec 14, 2025 Don't see what you're looking for? See all available trips from Columbus to Southern Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic holidays in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![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 $722 per person Mar 15 - Mar 19 found 11 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,003 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 ![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 $1,262 per person Mar 15 - Mar 19 found 11 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) From staff to room it was a amazing experience. Reviewed on Dec 18, 2025 ![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 $741 per person Mar 15 - Mar 19 found 10 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Clean and quiet room. Staff was ver helpful. Breakfast buffet was amazing! Only beef we had was that the room temperature was too hot!! Temp was 77degrees was only able to get down to 74\. Maintenance did bring us a fan. They could save on the heating bill by adjusting the furnace. Reviewed on Dec 18, 2025 Don't see what you're looking for? See all available trips from Columbus to Southern Wisconsin [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan unforgettable romantic Southern Wisconsin vacations #### What are some of the benefits of booking a romantic Southern Wisconsin vacation? When booking a romantic Southern Wisconsin vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in Wisconsin. #### How can I find the best vacation packages for couples? If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Southern Wisconsin destination, and you'll be met with an array of options for you and your partner to enjoy. #### Can I find cheap romantic vacations for 2 in Southern Wisconsin? Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $413 and can enjoy savings of up to 21 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first. #### What do I need to consider when booking a romantic getaway in Southern Wisconsin? Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Southern Wisconsin certainly come in handy here. #### What amenities should I look for in a luxury romantic vacation? If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Southern Wisconsin. #### Can I book a romantic Southern Wisconsin vacation with a hot tub? Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them. #### How can I find romantic vacation getaways that are all-inclusive? An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Southern Wisconsin search. #### Can I book a romantic trip to Southern Wisconsin that is fully refundable? Several romantic Southern Wisconsin vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements. #### Why should I book a romantic vacation with Expedia? Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage. ## More vacations you might like ![](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) ### Top Romantic Vacation Destinations > - [Romantic vacations in Toronto ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178314/Toronto) > - [Romantic vacations in Nova Scotia ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11173/Nova-Scotia) > - [Romantic vacations in Montreal ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178288/Montreal) > - [Romantic vacations in Vancouver ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178315/Vancouver) > - [Romantic vacations in Quebec ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/180017/Quebec) > - [Romantic vacations in the Niagara Falls ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/602721/Niagara-Falls) > - [Romantic vacations in Alberta ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11111/Alberta) > - [Romantic vacations in Victoria ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/1418/Victoria) > - [Romantic vacations in Jasper ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/8028/Jasper) > - [Romantic vacations in Banff ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/4332/Banff) > - [Romantic vacations in Ottawa ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178296/Ottawa) > - [Romantic vacations in Mont Tremblant ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/55374/Mont-Tremblant) > - [Romantic vacations in Kingston ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/180034/Kingston) > - [Romantic vacations in Whistler ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/4115/Whistler) > - [Romantic vacations in Winnipeg ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/6141041/Winnipeg) > - [Romantic vacations in Muskoka ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/6343146/Muskoka-District) > - [Romantic vacations in Collingwood ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11938/Collingwood) > - [Romantic vacations in Calgary ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178245/Calgary) > - [Romantic vacations in Canada ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/31/Canada) ## More Vacations Ideas [Flights to Southern Wisconsin ](https://expedia.ca/Cheap-Flights-To-Southern-Wisconsin.d553248635975749457.Travel-Guide-Flights)[ Southern Wisconsin Hotels ](https://expedia.ca/Southern-Wisconsin-Hotels.d553248635975749457.Travel-Guide-Hotels)[ Southern Wisconsin Vacation Rentals ](https://expedia.ca/Southern-Wisconsin-Vacation-Rentals.d553248635975749457.Travel-Guide-VacationRentals)[ Southern Wisconsin Car Rentals ](https://expedia.ca/Car-Rentals-In-Southern-Wisconsin.d553248635975749457.Car-Rental-Guide)[ Southern Wisconsin Vacations ](https://expedia.ca/Southern-Wisconsin.d553248635975749457.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app