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. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago £642 per person 1 Mar - 8 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff. Reviewed on 8 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 £1,162 per person 1 Mar - 8 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on 14 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 Save 100% on your flight £784 per person 1 Mar - 8 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Great location, clean room and friendly staff! Reviewed on 14 Dec 2025 ![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 Save 100% on your flight £803 per person 1 Mar - 8 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside Reviewed on 4 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 £1,332 per person 1 Mar - 8 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on 16 Dec 2025 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/2026-01-17/2026-01-24/?FromAirport=LON&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. ![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 £955 per person 1 Feb - 5 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,002 reviews) The room was spotless and the bed super comfy. The staff was very helpful and extremely courteous. Reviewed on 15 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 £1,162 per person 1 Mar - 8 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on 14 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 £1,332 per person 1 Mar - 8 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on 16 Dec 2025 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/2026-01-17/2026-01-24/?FromAirport=LON&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. ![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 £539 per person 1 Feb - 5 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) The room was beautiful and clean and a good city view of the city Reviewed on 26 Nov 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 £773 per person 1 Feb - 5 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on 14 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 £934 per person 16 Feb - 20 Feb found 8 hours ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on 16 Dec 2025 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/2026-01-17/2026-01-24/?FromAirport=LON&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 £539\. 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 > - [Family Friendly Holidays in France ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/59/France) > - [Family Friendly Holidays in Greece ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/67/Greece) > - [Family Friendly Holidays in Ibiza ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/1559/Ibiza-Town) > - [Family Friendly Holidays in Ireland ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/84/Ireland) > - [Family Friendly Holidays in Italy ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/86/Italy) > - [Family Friendly Holidays in Majorca ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/602317/Majorca-Island) > - [Family Friendly Holidays in Malta ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/111/Malta) > - [Family Friendly Holidays in Menorca ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/2201/Menorca) > - [Family Friendly Holidays in Morocco ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/122/Morocco) > - [Family Friendly Holidays in New Zealand ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/133/New-Zealand) > - [Family Friendly Holidays in Portugal ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/147/Portugal) > - [Family Friendly Holidays in Scotland ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/11219/Scotland) > - [Family Friendly Holidays in South Africa ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/165/South-Africa) > - [Family Friendly Holidays in Spain ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/166/Spain) > - [Family Friendly Holidays in the Canary Islands ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/180087/Canary-Islands) > - [Family Friendly Holidays in the United Kingdom ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/190/United-Kingdom) > - [Family Friendly Holidays in Turkey ](https://www.expedia.co.uk/lp/theme-holidays/kid-friendly-holidays/183/Turkey) ## More Holiday Ideas [Flights to Far Southwest Side ](https://expedia.co.uk/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights)[ Far Southwest Side Hotels ](https://expedia.co.uk/Far-Southwest-Side-Hotels.d553248635976475353.Travel-Guide-Hotels)[ Far Southwest Side Holiday Rentals ](https://expedia.co.uk/Far-Southwest-Side-Holiday-Rentals.d553248635976475353.Travel-Guide-HolidayRentals)[ Far Southwest Side Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Far-Southwest-Side.d553248635976475353.Car-Hire-Guide)[ Far Southwest Side Holidays ](https://expedia.co.uk/Far-Southwest-Side.d553248635976475353.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