Title: Southern Wisconsin Cheap 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 Cheap Holidays ## Book a Cheap 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 + Cheap hotel deals in Southern 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 24 hours 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 11 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 11 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 24 hours 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 10 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 Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-23/2026-01-30/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Cheap 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 Save 100% on your flight £1,142 per person 30 Jan - 5 Feb found 11 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 11 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 12 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 Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-23/2026-01-30/?FromAirport=LCY&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Cheap holidays in Southern 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 12 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 2 hours ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Courteous staff. Very clean rooms. Excellent location. Breakfast was wonderful (line starts forming around 9am). Self park nearby. Reasonably priced. Reviewed on 22 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 2 hours ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 8.2/10 Very Good! (2,158 reviews) It was smooth and very kind Reviewed on 17 Dec 2025 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/2026-01-23/2026-01-30/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Cheap holidays in Southern 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 24 hours 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 24 hours 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 24 hours ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Courteous staff. Very clean rooms. Excellent location. Breakfast was wonderful (line starts forming around 9am). Self park nearby. Reasonably priced. Reviewed on 22 Dec 2025 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/2026-01-23/2026-01-30/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 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) ## 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