Title: South Side All inclusive Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side All inclusive Holidays ## Book a All inclusive Hotel + Flight or Car together to unlock savings - ## 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 South Side 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 £807 per person 27 Apr - 1 May found 24 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Great staff, clean rooms. Great location Reviewed on 21 Feb 2026 ![Graduate by Hilton Evanston](https://images.trvl-media.com/lodging/2000000/1860000/1850700/1850638/d665c033_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Graduate by Hilton Evanston Downtown Evanston £1,171 per person 27 Apr - 4 May found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 8.8/10 Excellent! (1,001 reviews) Amazing staff and unique, very cool aesthetic Reviewed on 22 Feb 2026 ![InterContinental Chicago Magnificent Mile by IHG](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### InterContinental Chicago Magnificent Mile by IHG Downtown Chicago £945 per person 25 Apr - 30 Apr found 20 hours ago Return direct flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (2,558 reviews) Spotless clean, but the shower in one of the rooms wouldn’t get hot water. Reviewed on 20 Feb 2026 ![Viceroy Chicago](https://images.trvl-media.com/lodging/19000000/18620000/18614200/18614145/3aeed14b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Viceroy Chicago Downtown Chicago £1,494 per person 27 Apr - 4 May found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.4/10 Exceptional! (1,129 reviews) Clean room welcoming staff Reviewed on 21 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 £1,208 per person 27 Apr - 1 May found 24 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The view from our room was amazing. Everyone their is friendly and willing to help. The hotel is clean and inviting. Would recommend ten stars if I could. Reviewed on 22 Feb 2026 Don't see what you're looking for? See all available trips from London to South Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-22/2026-03-29/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive holidays in South Side 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 £1,208 per person 27 Apr - 1 May found 24 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The view from our room was amazing. Everyone their is friendly and willing to help. The hotel is clean and inviting. Would recommend ten stars if I could. Reviewed on 22 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 £1,541 per person 1 Apr - 6 Apr found 7 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) The room was comfortable and beautiful design. Comfortable bed and bedding. Large desk. Good walkable location. But we could hear sirens at night Reviewed on 16 Feb 2026 ![The Ritz-Carlton, Chicago](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/30b68b68_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton, Chicago Downtown Chicago £1,511 per person 2 Apr - 8 Apr found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,002 reviews) Great location, service, and gym Reviewed on 24 Jan 2026 Don't see what you're looking for? See all available trips from London to South Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-22/2026-03-29/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive holidays in South Side Price found within the past 48 hours. Click for updated prices. ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago Downtown Chicago £907 per person 8 Apr - 11 Apr found 2 hours ago Return flight included London (LHR) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Bathrooms and furniture was not clean at all. Splatter of dark brown-red substance on lampshade. Bathroom shower grout had similar brown-red stains and hair stuck in tub. Otherwise good. Room was spacious. Reviewed on 20 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 £1,182 per person 8 Apr - 11 Apr found 2 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The view from our room was amazing. Everyone their is friendly and willing to help. The hotel is clean and inviting. Would recommend ten stars if I could. Reviewed on 22 Feb 2026 ![The Blackstone, Autograph Collection](https://images.trvl-media.com/lodging/1000000/30000/22300/22295/5f1a18d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Blackstone, Autograph Collection Downtown Chicago £969 per person 8 Apr - 11 Apr found 2 hours ago Return flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) The room was fabulous. The only downside was no valet. Reviewed on 20 Feb 2026 Don't see what you're looking for? See all available trips from London to South Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-22/2026-03-29/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive holidays in South Side 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 £807 per person 27 Apr - 1 May found 24 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Great staff, clean rooms. Great location Reviewed on 21 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 £1,208 per person 27 Apr - 1 May found 24 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The view from our room was amazing. Everyone their is friendly and willing to help. The hotel is clean and inviting. Would recommend ten stars if I could. Reviewed on 22 Feb 2026 ![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 £1,061 per person 27 Apr - 1 May found 24 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium. Reviewed on 31 Jan 2026 Don't see what you're looking for? See all available trips from London to South Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-22/2026-03-29/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All-inclusive South Side holidays: everything you need to know #### Can I book South Side all-inclusive holidays with airfare and meals? Use the all-inclusive filter to find amazing all-inclusive package holidays to South Side, 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 South Side adults-only all-inclusive holiday? If screaming kids is your holiday nightmare, book a peaceful adults-only all-inclusive holiday to South Side 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 South Side? Last-minute breaks are a great way to find very cheap all-inclusive holidays to South Side. If you can be flexible with your holiday dates, browse our best South Side deals and use the all-inclusive filter to add everything that makes your hols perfect. #### Can I book a cheap all-inclusive South Side trip? There are some nifty little tricks to find pocket-friendly all-inclusive breaks in South Side. 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 £807 – 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 South Side? 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 South Side all-inclusive family holiday? If you’re holidaying with tots in tow, book an all-inclusive South Side 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 South Side in 2026/2027? There are great all-inclusive deals galore in South Side. 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 South Side 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 South Side package holiday with Expedia? With a huge range of all-inclusive South Side 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 South Side ](https://expedia.co.uk/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[ South Side Hotels ](https://expedia.co.uk/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[ South Side Holiday Rentals ](https://expedia.co.uk/South-Side-Holiday-Rentals.d553248635074842823.Travel-Guide-HolidayRentals)[ South Side Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-South-Side.d553248635074842823.Car-Hire-Guide)[ South Side Holidays ](https://expedia.co.uk/South-Side.d553248635074842823.Holidays-City-Breaks)[ Things to do in South Side ](https://expedia.co.uk/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities) \* 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