Title: Far Southwest Side All inclusive Holidays 2026 | Expedia.co.uk ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Far Southwest 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 Far Southwest Side 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 £680 per person 5 Mar - 9 Mar found 12 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on 8 Jan 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago Save 100% on your flight £1,234 per person 2 Apr - 7 Apr found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on 20 Jan 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 £867 per person 5 Mar - 9 Mar found 12 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Exceptional service, great location, beautiful hotel Reviewed on 20 Jan 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 £983 per person 31 Mar - 4 Apr found 16 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) No parking available, the hotel was nice, room etc. but breakfast was overly crowded, cafeteria style. They say breakfast is free with stay but then I was charged $85\. When I asked what the charge was for they said for breakfast, room service etc. plus parking was an additional $150, not on site so not too pleased with the overall experience. Staff was very nice though. Reviewed on 22 Jan 2026 ![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 £1,060 per person 31 Mar - 4 Apr found 16 hours ago Return flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on 18 Jan 2026 Don't see what you're looking for? See all available trips from London to Far Southwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-22/2026-03-01/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive holidays in Far Southwest 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 £867 per person 5 Mar - 9 Mar found 12 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Exceptional service, great location, beautiful hotel Reviewed on 20 Jan 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago Save 100% on your flight £1,234 per person 2 Apr - 7 Apr found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on 20 Jan 2026 ![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 £926 per person 5 Mar - 9 Mar found 12 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Yes didn’t know you get free breakfast Reviewed on 4 Jan 2026 Don't see what you're looking for? See all available trips from London to Far Southwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-22/2026-03-01/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive holidays in Far Southwest 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 £726 per person 2 Mar - 5 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) No parking available, the hotel was nice, room etc. but breakfast was overly crowded, cafeteria style. They say breakfast is free with stay but then I was charged $85\. When I asked what the charge was for they said for breakfast, room service etc. plus parking was an additional $150, not on site so not too pleased with the overall experience. Staff was very nice though. Reviewed on 22 Jan 2026 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago £895 per person 2 Mar - 5 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Everything about this hotel is special. Great staff- awesome restaurant/bar. Location is perfect. This hotel is my destination every time I come to the city. Which is quite often. Reviewed on 20 Jan 2026 ![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 £861 per person 2 Mar - 5 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Great staff that paid attention quickly to concerns. Reviewed on 19 Jan 2026 Don't see what you're looking for? See all available trips from London to Far Southwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-22/2026-03-01/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive holidays in Far Southwest Side 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 £680 per person 5 Mar - 9 Mar found 12 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on 8 Jan 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 £867 per person 5 Mar - 9 Mar found 12 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Exceptional service, great location, beautiful hotel Reviewed on 20 Jan 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 £983 per person 31 Mar - 4 Apr found 16 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) No parking available, the hotel was nice, room etc. but breakfast was overly crowded, cafeteria style. They say breakfast is free with stay but then I was charged $85\. When I asked what the charge was for they said for breakfast, room service etc. plus parking was an additional $150, not on site so not too pleased with the overall experience. Staff was very nice though. Reviewed on 22 Jan 2026 Don't see what you're looking for? See all available trips from London to Far Southwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-22/2026-03-01/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All-inclusive Far Southwest Side holidays: everything you need to know #### Can I book Far Southwest Side all-inclusive holidays with airfare and meals? Use the all-inclusive filter to find amazing all-inclusive package holidays to Far Southwest 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 Far Southwest Side adults-only all-inclusive holiday? If screaming kids is your holiday nightmare, book a peaceful adults-only all-inclusive holiday to Far Southwest 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 Far Southwest Side? Last-minute breaks are a great way to find very cheap all-inclusive holidays to Far Southwest Side. If you can be flexible with your holiday dates, browse our best Far Southwest Side deals and use the all-inclusive filter to add everything that makes your hols perfect. #### Can I book a cheap all-inclusive Far Southwest Side trip? There are some nifty little tricks to find pocket-friendly all-inclusive breaks in Far Southwest 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 £680 – 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 Far Southwest 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 Far Southwest Side all-inclusive family holiday? If you’re holidaying with tots in tow, book an all-inclusive Far Southwest 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 Far Southwest Side in 2026/2027? There are great all-inclusive deals galore in Far Southwest 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 Far Southwest 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 Far Southwest Side package holiday with Expedia? With a huge range of all-inclusive Far Southwest 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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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