Title: Southwest Wisconsin All inclusive Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/5957/f96cbf4a-3a46-4cf7-b7f2-0fff893f2f53.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southwest Wisconsin All inclusive Holidays ## Book a All inclusive Hotel + Flight or Car together to unlock savings Photo by Inbal Arieh - ## 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 Southwest 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 £1,141 per person 20 Jun - 25 Jun found 11 hours ago Return direct flight included London (LHR) to Chicago (ORD) 8.2/10 Very Good! (2,582 reviews) Big shoutout to Marina. Thank you for the hospitality and being so kind and helpful to me during my stay. Chicago is great!! Reviewed on 30 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 £1,279 per person 20 Jun - 25 Jun found 11 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Clean room , staff are friendly , breakfast is amazing just the rooftop bar was closed due to the winter season Reviewed on 31 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 £2,099 per person 2 May - 9 May found 21 hours ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,852 reviews) Quality staff and the property was well appointed Reviewed on 30 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 £1,922 per person 2 May - 9 May found 21 hours ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,140 reviews) Staff really friendly and hotel was clean and close to everything around the city can’t wait to come back. Reviewed on 23 Mar 2026 ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars Magnificent Mile Downtown Chicago £1,353 per person 22 Jun - 27 Jun found 9 hours ago Return flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (3,314 reviews) Location was ideal for public transit. Clean and safe. House keeping staff did wonderful job no matter the time of day. Reviewed on 31 Mar 2026 Don't see what you're looking for? See all available trips from London to Southwest Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=LHR&Destination=RFD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive holidays in Southwest Wisconsin Price found within the past 48 hours. Click for updated prices. ![Four Seasons Hotel Chicago](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/e5b56b9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Four Seasons Hotel Chicago Downtown Chicago £1,835 per person 21 May - 26 May found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.4/10 Exceptional! (999 reviews) Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay! Reviewed on 27 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 £2,099 per person 2 May - 9 May found 21 hours ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,852 reviews) Quality staff and the property was well appointed Reviewed on 30 Mar 2026 ![The Ritz-Carlton, Chicago](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/29a217ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton, Chicago Downtown Chicago £2,157 per person 3 May - 8 May just found Return direct flight included Manchester (MAN) to Chicago (ORD) 9.2/10 Wonderful! (1,001 reviews) Enjoyed a very comfortable stay. Reviewed on 30 Mar 2026 Don't see what you're looking for? See all available trips from Manchester to Southwest Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=MAN&Destination=RFD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive holidays in Southwest Wisconsin Price found within the past 48 hours. Click for updated prices. ![Lodge Geneva National](https://images.trvl-media.com/lodging/1000000/900000/893400/893361/c30b4670_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lodge Geneva National £1,225 per person 25 Jun - 28 Jun found 1 day ago Return flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (1,366 reviews) Everything was great!! Reviewed on 30 Mar 2026 ![Destination Geneva National](https://images.trvl-media.com/lodging/1000000/900000/893400/893359/74cd8c6b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Destination Geneva National £1,325 per person 25 Jun - 28 Jun found 1 day ago Return flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (496 reviews) This property has some amazing amenities, and is beautiful! It is a great place to come and relax. Reviewed on 16 Mar 2026 Don't see what you're looking for? See all available trips from London to Southwest Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=LON&Destination=RFD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive holidays in Southwest 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 £1,322 per person 22 Jun - 26 Jun found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Clean room , staff are friendly , breakfast is amazing just the rooftop bar was closed due to the winter season Reviewed on 31 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 £1,794 per person 22 Jun - 26 Jun found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,852 reviews) Quality staff and the property was well appointed Reviewed on 30 Mar 2026 ![Hilton Garden Inn Chicago Downtown Riverwalk](https://images.trvl-media.com/lodging/12000000/11510000/11501300/11501235/w3837h2556x3y3-5469aeb6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Chicago Downtown Riverwalk Downtown Chicago £1,574 per person 22 Jun - 26 Jun found 1 day ago Return flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (1,874 reviews) The hotel was very close to anywhere Reviewed on 29 Mar 2026 Don't see what you're looking for? See all available trips from London to Southwest Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=LON&Destination=RFD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All-inclusive Southwest Wisconsin holidays: everything you need to know #### Can I book Southwest Wisconsin all-inclusive holidays with airfare and meals? Use the all-inclusive filter to find amazing all-inclusive package holidays to Southwest 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 Southwest Wisconsin adults-only all-inclusive holiday? If screaming kids is your holiday nightmare, book a peaceful adults-only all-inclusive holiday to Southwest 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 Southwest Wisconsin? Last-minute breaks are a great way to find very cheap all-inclusive holidays to Southwest Wisconsin. If you can be flexible with your holiday dates, browse our best Southwest Wisconsin deals and use the all-inclusive filter to add everything that makes your hols perfect. #### Can I book a cheap all-inclusive Southwest Wisconsin trip? There are some nifty little tricks to find pocket-friendly all-inclusive breaks in Southwest 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 £1,141 – 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 Southwest 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 Southwest Wisconsin all-inclusive family holiday? If you’re holidaying with tots in tow, book an all-inclusive Southwest 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 Southwest Wisconsin in 2026/2027? There are great all-inclusive deals galore in Southwest 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 Southwest 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 Southwest Wisconsin package holiday with Expedia? With a huge range of all-inclusive Southwest 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 > - 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[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 Southwest Wisconsin ](https://expedia.co.uk/Cheap-Flights-To-Southwest-Wisconsin.d6059824.Travel-Guide-Flights)[ Southwest Wisconsin Hotels ](https://expedia.co.uk/Southwest-Wisconsin-Hotels.d6059824.Travel-Guide-Hotels)[ Southwest Wisconsin Holiday Rentals ](https://expedia.co.uk/Southwest-Wisconsin-Holiday-Rentals.d6059824.Travel-Guide-HolidayRentals)[ Southwest Wisconsin Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southwest-Wisconsin.d6059824.Car-Hire-Guide)[ Southwest Wisconsin Holidays ](https://expedia.co.uk/Southwest-Wisconsin.d6059824.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