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. ![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 £654 per person 5 Mar - 9 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Great location! Very helpful staff! Reviewed on 22 Dec 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 Save 100% on your flight £1,142 per person 30 Jan - 5 Feb found 15 hours ago Return flight included London (LCY) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Loved it here and would stay again! Everything was perfect! Reviewed on 21 Dec 2025 ![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 £1,331 per person 30 Jan - 5 Feb found 15 hours ago Return flight included London (LCY) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Service and clean room - paying attention to the details Reviewed on 22 Dec 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 £654 per person 5 Mar - 9 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Great location, clean room and friendly staff! Reviewed on 14 Dec 2025 ![Chicago Athletic Association, a Hyatt Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/6b24bc12_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chicago Athletic Association, a Hyatt Hotel Downtown Chicago £715 per person 30 Jan - 5 Feb found 14 hours ago Return flight included London (LCY) to Chicago (ORD) 9/10 Wonderful! (1,002 reviews) Simply, amazing stay. Reviewed on 21 Dec 2025 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/2026-01-23/2026-01-30/?FromAirport=LON&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. ![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 Save 100% on your flight £1,142 per person 30 Jan - 5 Feb found 15 hours ago Return flight included London (LCY) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Loved it here and would stay again! Everything was perfect! Reviewed on 21 Dec 2025 ![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 £1,331 per person 30 Jan - 5 Feb found 15 hours ago Return flight included London (LCY) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Service and clean room - paying attention to the details Reviewed on 22 Dec 2025 ![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 £1,151 per person 18 Mar - 22 Mar found 16 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Langham is always a superior stay Reviewed on 1 Dec 2025 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/2026-01-23/2026-01-30/?FromAirport=LCY&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. ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago £495 per person 30 Jan - 2 Feb found 16 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Aisha, Diamond and Natalie at thr front desk are always so incredibly helpful and accommodating. This is my favorite place to stay in downtown Chicago. Fabulous views. Full kitchen. Washer/dryer. Balcony. Best of Chicago! Truly Reviewed on 15 Dec 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 £752 per person 4 Feb - 7 Feb found 7 hours ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Location is the best. Reviewed on 23 Dec 2025 ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago O'Hare Airport O'Hare £873 per person 4 Feb - 7 Feb found 7 hours ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 8.2/10 Very Good! (2,158 reviews) It was ok. Wouldn’t want to stay longer than a night. Food was pretty bad, room cramped Reviewed on 23 Dec 2025 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/2026-01-23/2026-01-30/?FromAirport=LHR&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. ![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 £654 per person 5 Mar - 9 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Great location, clean room and friendly staff! Reviewed on 14 Dec 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 £875 per person 5 Mar - 9 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Loved it here and would stay again! Everything was perfect! Reviewed on 21 Dec 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 £789 per person 12 Mar - 16 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Location is the best. Reviewed on 23 Dec 2025 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/2026-01-23/2026-01-30/?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 £495 – 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 2026/2026? 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