Title: Southern Wisconsin All inclusive 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 All inclusive Holidays ## Book a All inclusive 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 + All inclusive hotel deals 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 Save 100% on your flight £1,020 per person 3 Jun - 7 Jun found 9 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel Reviewed on 10 Mar 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago Save 100% on your flight £1,715 per person 3 Jun - 9 Jun found 16 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,839 reviews) One of the best hotels I've ever stayed at Reviewed on 10 Mar 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago Save 100% on your flight £1,386 per person 3 Jun - 9 Jun found 16 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (3,613 reviews) My stay at LondonHouse Chicago was absolutely amazing from start to finish. The hotel itself is beautiful and perfectly located, offering stunning views of the river and city skyline. The restaurants were excellent, with delicious food and a great atmosphere. The rooftop experience was definitely a highlight and made the stay feel even more special. I also had the chance to visit the spa, which was incredibly relaxing and well done. The environment was peaceful, the service was top-tier, and it was the perfect way to unwind during my trip. Overall, everything—from the service to the amenities—was exceptional. I would definitely book again and highly recommend LondonHouse Chicago to anyone visiting the city. ⭐⭐⭐⭐⭐ Reviewed on 10 Mar 2026 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago £1,609 per person 3 Jun - 9 Jun found 16 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,137 reviews) Great location, clean and very nice restaurant and bar. Reviewed on 9 Mar 2026 Don't see what you're looking for? See all available trips from Dublin to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-11/2026-04-18/?FromAirport=DUB&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive holidays in Southern Wisconsin Price found within the past 48 hours. Click for updated prices. ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c8149674_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago £1,380 per person 26 Apr - 30 Apr found 8 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.6/10 Exceptional! (1,003 reviews) The room was a little dated. I was surprised that you didn’t have CNBC as a TV choice, I thought the gym was dated and the WiFi was inadequate Reviewed on 28 Feb 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago Save 100% on your flight £1,715 per person 3 Jun - 9 Jun found 16 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,839 reviews) One of the best hotels I've ever stayed at Reviewed on 10 Mar 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago £1,480 per person 26 Apr - 30 Apr found 8 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (1,004 reviews) Nice bellmen, nice front staff, rooms were cozy and well kept. Everyone was very friendly and helpful. We would stay again. Reviewed on 1 Mar 2026 Don't see what you're looking for? See all available trips from Dublin to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-11/2026-04-18/?FromAirport=DUB&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive holidays 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/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Felix River North/Magnificent Mile Downtown Chicago £804 per person 4 Jun - 7 Jun found 9 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 8.2/10 Very Good! (2,573 reviews) the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back. Reviewed on 4 Mar 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 £924 per person 4 Jun - 7 Jun found 9 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel Reviewed on 10 Mar 2026 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago £969 per person 4 Jun - 7 Jun found 9 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.2/10 Wonderful! (1,310 reviews) Very cool, gorgeous hotel. The rooms offered a lot of amenities and had a fun industrial vibe. The bed was very comfortable, and we slept great! The staff was incredibly helpful. I would definitely stay at The Emily again. Reviewed on 7 Mar 2026 Don't see what you're looking for? See all available trips from Dublin to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-11/2026-04-18/?FromAirport=DUB&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive holidays 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/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Felix River North/Magnificent Mile Downtown Chicago £853 per person 3 Jun - 7 Jun found 9 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 8.2/10 Very Good! (2,573 reviews) the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back. Reviewed on 4 Mar 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 £1,020 per person 3 Jun - 7 Jun found 9 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel Reviewed on 10 Mar 2026 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago £1,093 per person 3 Jun - 7 Jun found 9 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.2/10 Wonderful! (1,310 reviews) Very cool, gorgeous hotel. The rooms offered a lot of amenities and had a fun industrial vibe. The bed was very comfortable, and we slept great! The staff was incredibly helpful. I would definitely stay at The Emily again. Reviewed on 7 Mar 2026 Don't see what you're looking for? See all available trips from Dublin to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-11/2026-04-18/?FromAirport=DUB&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All-inclusive Southern Wisconsin holidays: everything you need to know #### Can I book Southern Wisconsin all-inclusive holidays with airfare and meals? Use the all-inclusive filter to find amazing all-inclusive package holidays to Southern Wisconsin, then just add on your flights with a few simple clicks. With everything from cocktails to car hire booked in one go, all you need to decide is whether you’ll be sipping a mojito or a margarita at sunset. #### Why should I book a Southern Wisconsin adults-only all-inclusive holiday? If screaming kids is your holiday nightmare, book a peaceful adults-only all-inclusive holiday to Southern Wisconsin and you’re pretty much guaranteed a dreamy retreat. With those thoughtful grownup touches – beachside massage beds and live after-dinner music – an adults-only hotel levels up the sophistication on your holiday. #### Can I book last minute all-inclusive holidays to Southern Wisconsin? Last-minute breaks are a great way to find very cheap all-inclusive holidays to Southern Wisconsin. If you can be flexible with your holiday dates, browse our best Southern Wisconsin deals and use the all-inclusive filter to add everything that makes your hols perfect. #### Can I book a cheap all-inclusive Southern Wisconsin trip? There are some nifty little tricks to find pocket-friendly all-inclusive breaks in Southern Wisconsin. Try hunting around for cheaper deals in the off season by playing with your dates. Or you could also choose an all-inclusive hotel or resort a little off the beaten track. We have some top value deals starting at £804 – and they’re easy to find if you sort your results by price. Prices and availability are subject to change. Additional terms may apply. #### What should I look for when booking a 5-star all-inclusive holiday to Southern Wisconsin? All-inclusive holidays are such a treat, but a 5-star all-inclusive is a whole other level of luxury. Think butlers waiting on your every whim, infinity pools with epic ocean views and unlimited spa-ing for holiday heaven on cloud nine. #### What should I consider when booking a Southern Wisconsin all-inclusive family holiday? If you’re holidaying with tots in tow, book an all-inclusive Southern Wisconsin package with all the kid-friendly amenities. The action-packed kids’ clubs, the slide-tastic water parks, the fussy-eater-friendly restaurants: we have a stack of deals specifically designed with kids in mind. #### How can I find the best deals on all-inclusive holidays to Southern Wisconsin in 2026/2027? There are great all-inclusive deals galore in Southern Wisconsin. Sort by price to see the cheapest places to stay, and consider travelling during the less popular months when there’s often more availability and better prices. #### Can I book an all-inclusive Southern Wisconsin package with free cancellation and/or flexible dates? Flexibility is key to a stress-free holiday. Look for properties with free cancellation or book now, pay later options. Then, if your plans change, just login to make changes in a few clicks. #### Why should I book an all-inclusive Southern Wisconsin package holiday with Expedia? With a huge range of all-inclusive Southern Wisconsin trips on offer, Expedia is your go-to place to find and book your trip. It’s super easy … and it’s all here. ## 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 All inclusive Holiday Destinations > - [All Inclusive Holidays to Antigua ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/11729/Antigua) > - [All Inclusive Holidays to Azores ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/6048267/Azores) > - [All Inclusive Holidays to Benidorm ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/181363/Benidorm) > - [All Inclusive Holidays to Bora Bora ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/602861/Bora-Bora) > - [All Inclusive Holidays to Cairo ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/178243/Cairo) > - [All Inclusive Holidays to Canary Islands ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/180087/Canary-Islands) > - [All Inclusive Holidays to Corsica ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/6049372/Corsica) > - [All Inclusive Holidays to Croatia ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/43/Croatia) > - [All Inclusive Holidays to Cyprus ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/45/Cyprus) > - [All Inclusive Holidays to Dominican Republic ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/50/Dominican-Republic) > - [All Inclusive Holidays to Dubai ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/1079/Dubai) > - [All Inclusive Holidays to Egypt ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/52/Egypt) > - [All Inclusive Holidays to Gran Canaria ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/6047134/Gran-Canaria) > - [All Inclusive Holidays to Greece ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/67/Greece) > - [All Inclusive Holidays to Ibiza ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/1559/Ibiza-Town) > - [All Inclusive Holidays to India ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/80/India) > - [All Inclusive Holidays to Italy ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/86/Italy) > - [All Inclusive Holidays to Lanzarote ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/282/Lanzarote) > - [All Inclusive Holidays to Majorca ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/602317/Majorca-Island) > - [All Inclusive Holidays to Maldives ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/109/Maldives) > - [All Inclusive Holidays to Malta ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/111/Malta) > - [All Inclusive Holidays to Mexico ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/117/Mexico) > - [All Inclusive Holidays to Portugal ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/147/Portugal) > - [All Inclusive Holidays to Spain ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/166/Spain) > - [All Inclusive Holidays to Split ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/3255/Split) > - [All Inclusive Holidays to Tenerife ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/6047194/Tenerife) > - [All Inclusive Holidays to Thailand ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/178/Thailand) > - [All Inclusive Holidays to Turkey ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/183/Turkey) > - [All Inclusive Holidays to UK ](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/190/United-Kingdom) ## 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