Title: Southern Wisconsin Romantic Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/2325/f29f5e3d-0eb0-45b8-94f1-06284f8af3d0.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southern Wisconsin Romantic Holidays ## Book a Romantic Hotel + Flight or Car together to unlock savings Photo by Evae - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected ## Top flight + Romantic hotel deals in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Felix River North/Magnificent Mile Downtown Chicago £672 per person 24 Apr - 1 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 8.2/10 Very Good! (2,365 reviews) There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again. Reviewed on 2 Feb 2026 ![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 Save 100% on your flight £849 per person 24 Apr - 1 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) I had an Amazing staycation Reviewed on 8 Feb 2026 ![Arlo Chicago](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/747fff56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arlo Chicago Downtown Chicago £814 per person 24 Apr - 1 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,862 reviews) Room was clean but the soap dispenser at the sync and in shower were not working as it supposed to. Reviewed on 5 Feb 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 £761 per person 24 Apr - 1 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 8.4/10 Very Good! (1,444 reviews) The view from my room was stunning Reviewed on 7 Feb 2026 ![Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/886bf093_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel Downtown Chicago £818 per person 24 Apr - 1 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.6/10 Exceptional! (1,067 reviews) Clean spacious room with toiletries from Crabtree & Evelyn. Very comfy bed, nice decorating, lovely view Reviewed on 6 Feb 2026 Don't see what you're looking for? See all available trips from London to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-08/2026-03-15/?FromAirport=LON&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. ![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 £901 per person 14 Mar - 17 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Lovely room. Excellent staff. Reviewed on 3 Feb 2026 ![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 Save 100% on your flight £1,768 per person 24 Apr - 1 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) The staff and amenities Reviewed on 4 Feb 2026 ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago £1,180 per person 19 Mar - 24 Mar found 9 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Gorgeous property, facilities, and location. Reviewed on 6 Feb 2026 Don't see what you're looking for? See all available trips from London to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-08/2026-03-15/?FromAirport=LON&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. ![Arlo Chicago](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/747fff56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arlo Chicago Downtown Chicago £705 per person 14 Mar - 17 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,862 reviews) Room was clean but the soap dispenser at the sync and in shower were not working as it supposed to. Reviewed on 5 Feb 2026 ![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 £714 per person 14 Mar - 17 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) I had an Amazing staycation Reviewed on 8 Feb 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 £901 per person 14 Mar - 17 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Lovely room. Excellent staff. Reviewed on 3 Feb 2026 Don't see what you're looking for? See all available trips from London to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-08/2026-03-15/?FromAirport=LON&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. ![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 £923 per person 16 Mar - 20 Mar found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) I had an Amazing staycation Reviewed on 8 Feb 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 £1,206 per person 16 Mar - 20 Mar found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Lovely room. Excellent staff. Reviewed on 3 Feb 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 £928 per person 1 Apr - 5 Apr found 5 hours ago Return flight included London (LON) 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 2 Feb 2026 Don't see what you're looking for? See all available trips from Manchester to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-08/2026-03-15/?FromAirport=MAN&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## How to find a romantic Southern Wisconsin holiday #### How can I find the best Southern Wisconsin vacation packages for couples? Use our easy-to-use holiday search tools to plan your most-romantic getaway to Southern Wisconsin. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino. #### Can I book cheap Southern Wisconsin romantic holidays for two? Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Southern Wisconsin that start from £672\. Prices and availability are subject to change. Additional terms may apply. #### What should I think about when booking a Southern Wisconsin romantic getaway? The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure. #### What should I look for in a luxury romantic holiday to Southern Wisconsin? Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service. #### Can I book a romantic hot-tub holiday in Southern Wisconsin? What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter. #### How can I find romantic holidays for couples in Southern Wisconsin that are all inclusive? Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available. #### Can I book a romantic trip to Southern Wisconsin with free cancellation and/or flexible dates? Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print. #### Why should I book my Southern Wisconsin romantic holiday with Expedia? At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing. ## More holidays 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 Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.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 Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holiday packages](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Top Romantic Holiday Destinations > - [Romantic Holidays in Barcelona ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179992/Barcelona) > - [Romantic Holidays in Cornwall ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/10558/Cornwall) > - [Romantic Holidays in Cyprus ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/45/Cyprus) > - [Romantic Holidays in France ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/59/France) > - [Romantic Holidays in Greece ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/67/Greece) > - [Romantic Holidays in Ibiza ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/1559/Ibiza-Town) > - [Romantic Holidays in Italy ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/86/Italy) > - [Romantic Holidays in Morocco ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/122/Morocco) > - [Romantic Holidays in Paris ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179898/Paris) > - [Romantic Holidays in Portugal ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/147/Portugal) > - [Romantic Holidays in Rome ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179899/Rome) > - [Romantic Holidays in Santorini ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/177970/Santorini) > - [Romantic Holidays in Scotland ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/11219/Scotland) > - [Romantic Holidays in Thailand ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/178/Thailand) > - [Romantic Holidays in the Maldives ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/109/Maldives) > - [Romantic Holidays in the United Kingdom ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/190/United-Kingdom) > - [Romantic Holidays in the USA ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/201/United-States-Of-America) > - [Romantic Holidays in Turkey ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/183/Turkey) > - [Romantic Holidays in Venice ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179981/Venice) ## More Holiday Ideas [Flights to Southern Wisconsin ](https://expedia.co.uk/Cheap-Flights-To-Southern-Wisconsin.d553248635975749457.Travel-Guide-Flights)[ Southern Wisconsin Hotels ](https://expedia.co.uk/Southern-Wisconsin-Hotels.d553248635975749457.Travel-Guide-Hotels)[ Southern Wisconsin Holiday Rentals ](https://expedia.co.uk/Southern-Wisconsin-Holiday-Rentals.d553248635975749457.Travel-Guide-HolidayRentals)[ Southern Wisconsin Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southern-Wisconsin.d553248635975749457.Car-Hire-Guide)[ Southern Wisconsin Holidays ](https://expedia.co.uk/Southern-Wisconsin.d553248635975749457.Holidays-City-Breaks) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in 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