Title: Far Southwest Side Kid friendly 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 Kid friendly Holidays ## Book a Kid friendly 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 + Kid friendly hotel deals in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![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 £1,065 per person 26 Mar - 1 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again. Reviewed on 25 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 £1,461 per person 27 Mar - 1 Apr found 13 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Lovely room. Excellent staff. Reviewed on 3 Feb 2026 ![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Virgin Hotels Chicago Downtown Chicago £1,079 per person 25 Apr - 1 May found 1 hour ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.2/10 Wonderful! (1,404 reviews) Staff was super friendly and rooms were clean. Definitely will come back 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 £2,559 per person 1 May - 6 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on 26 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 £1,098 per person 27 Mar - 1 Apr found 13 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Staff was extremely polite, rooms were clean. No issues at all Reviewed on 2 Feb 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/2026-03-06/2026-03-13/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Kid friendly 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 £1,461 per person 27 Mar - 1 Apr found 13 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Lovely room. Excellent staff. Reviewed on 3 Feb 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 £2,114 per person 14 Mar - 21 Mar found 7 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on 26 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 £2,042 per person 14 Mar - 21 Mar found 7 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Staff was wonderful. Reviewed on 25 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/2026-03-06/2026-03-13/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Kid friendly holidays in Far Southwest Side 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 £911 per person 27 Apr - 1 May found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Great stay. Would come again. Reviewed on 19 Jan 2026 ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago £998 per person 27 Apr - 1 May found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) Service was amazing and the location was perfect. Would definitely stay here again. Reviewed on 28 Jan 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 £1,018 per person 27 Apr - 1 May found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9/10 Wonderful! (2,558 reviews) We recently stayed at the InterContinental to celebrate my youngest son’s birthday. Overall, the room was clean, and the staff was attentive, which we really appreciated. My only issue was that upon arrival, our room was extremely cold. We contacted the staff, and while they assured us engineering would address it, hours later the room was still freezing. We were then moved to another room on a lower floor. While we understand issues happen, the inconvenience was significant, and I feel that some form of compensation, such as a small incentive or price adjustment, would have been appropriate. Reviewed on 3 Feb 2026 Don't see what you're looking for? See all available trips from Manchester to Far Southwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-06/2026-03-13/?FromAirport=MAN&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## FAQs: family holidays in Far Southwest Side #### How can I find the best family-friendly holidays in Far Southwest Side? At Expedia, it’s super-easy to find family-friendly holidays in Far Southwest Side in our vast inventory. Use our handy filters to find hotels and resorts with the best reviews, most amenities and lowest price tags. You can also hunt out great flights and smashing deals on car hire, so you can book the whole shebang in one place. #### Are there any cheap Far Southwest Side family holidays? Avoid forking out for multiple hotel rooms by booking a villa or apartment with a kitchen and give your brood plenty of space and all the meals they love at a fraction of the cost. Find the most affordable family holidays by filtering your search by price. Generally, Far Southwest Side family getaways start at £911\. Prices and availability are subject to change and additional terms may apply. #### Can I book an all-inclusive Far Southwest Side family holiday package? All-inclusive holidays can keep the costs down when you’re travelling as a family. Think unlimited mocktails for the little'uns and double doses of gin for the bigguns. Use our all-inclusive filter to see what’s available in Far Southwest Side and book the whole package in just a few clicks. #### How can I book the best family activity holiday in Far Southwest Side? Family holidays are all about spending quality time together, laughing, playing and bonding as you try new things. Pack your trip full of family activities they’ll love and make memories that’ll last a lifetime. #### Can I find luxury family holidays in Far Southwest Side? To treat the kids to a luxury holiday they’ll never forget, take a look at the most indulgent hotels and resorts in Far Southwest Side by using our 5-star filter. To really travel in style, use the first-class filter to find the best flights, too. #### How can I search for Far Southwest Side family holiday deals? Start by entering your dates, then use the family-friendly filter to narrow down your search to show the best available Far Southwest Side family holiday deals. If your travel dates are flexible, play around to see if you can find cheaper options or more availability at different times. #### Can I book a Far Southwest Side family vacation package with free cancellation and/or flexible dates? Plans change, so booking a family holiday with free cancellation is a great way to ensure you don’t lose out if they do. Use the fully refundable and reserve now pay later filters to find flexibility. Make sure you always check terms and conditions, too. #### Why should I book my Far Southwest Side family trip with Expedia? Forget family fights and start thinking about family flights. Our huge selection of easy to browse family-friendly holidays means you can find and book your dream family trip to Far Southwest Side in no time. ## 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 Kid friendly 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