Title: Chicago Kid friendly Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chicago 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 Chicago Price found within the past 48 hours. Click for updated prices. ![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Warwick Allerton - Chicago Downtown Chicago £754 per person 12 Mar - 19 Mar found 3 hours ago Return direct flight included Dublin (DUB) to Chicago (ORD) 8.4/10 Very Good! (2,972 reviews) The staff was the best part, thank you Marcus! This made the stay, at this beautiful hotel. In a world that can seem disconnected, Marcus greeted us with a warm smile, a firm handshake, and gave us the lay of the land. His kind heart was welcoming and engaged. Finding amazing staff like this is hard to come by (coming from a a hospitality background). Our room was spotless and very comfortable. The common areas and hallways were clean and welcoming. I will recommend this hotel! Reviewed on 23 Jan 2026 ![Omni Chicago Hotel](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/433c2c13_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni Chicago Hotel Downtown Chicago £923 per person 4 May - 8 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,603 reviews) Nice restaurant, attentive staff. Reviewed on 7 Feb 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 £879 per person 16 Apr - 20 Apr found 20 hours ago Return flight included London (LHR) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Outdated rooms and our heater stopped working overnight and the temp fell to 60's which felt freezing given it was zero outside with snow flurries But Matt the maintenance guy came quickly at 6 am thankfully and got it back up and running. Other than that, a truly beautiful hotel and the restaurant staff and front desk guys were amazing! Reviewed on 8 Feb 2026 ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Chicago Downtown Chicago £979 per person 16 Apr - 20 Apr found 20 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (3,386 reviews) Spacious and clean room but improvement points on amenities (missing tissue in tissue casing, need to call for amenities, nondairy milk available but not dairy milk, dirty coffee maker cannot make tea), dark, and separate towers inconvenient with friends & availability of lifts during conference season low. Road works and access by car/cab not warned Reviewed on 10 Feb 2026 ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Royal Sonesta Chicago Downtown Downtown Chicago £838 per person 23 Mar - 26 Mar found 23 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (3,062 reviews) Fantastic stay! Will be a return customer when in chicago Reviewed on 10 Feb 2026 Don't see what you're looking for? See all available trips from Dublin to Chicago [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-10/2026-03-17/?FromAirport=DUB&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Kid friendly holidays in Chicago Price found within the past 48 hours. Click for updated prices. ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Royal Sonesta Chicago Downtown Downtown Chicago £838 per person 23 Mar - 26 Mar found 23 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (3,062 reviews) Fantastic stay! Will be a return customer when in chicago Reviewed on 10 Feb 2026 ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Palmer House a Hilton Hotel Downtown Chicago £886 per person 23 Mar - 26 Mar found 23 hours ago Return direct flight included London (LON) to Chicago (ORD) 8.4/10 Very Good! (2,059 reviews) Clean room, nice size. Housekeeping staff in particular were very nice and helpful. No coffee maker in the room, hence 4 vs 5 stars. Reviewed on 10 Feb 2026 ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Chicago Downtown Chicago £926 per person 23 Mar - 26 Mar found 23 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (3,386 reviews) Spacious and clean room but improvement points on amenities (missing tissue in tissue casing, need to call for amenities, nondairy milk available but not dairy milk, dirty coffee maker cannot make tea), dark, and separate towers inconvenient with friends & availability of lifts during conference season low. Road works and access by car/cab not warned Reviewed on 10 Feb 2026 Don't see what you're looking for? See all available trips from London to Chicago [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-10/2026-03-17/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Kid friendly holidays in Chicago 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 £879 per person 16 Apr - 20 Apr found 20 hours ago Return flight included London (LHR) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Outdated rooms and our heater stopped working overnight and the temp fell to 60's which felt freezing given it was zero outside with snow flurries But Matt the maintenance guy came quickly at 6 am thankfully and got it back up and running. Other than that, a truly beautiful hotel and the restaurant staff and front desk guys were amazing! Reviewed on 8 Feb 2026 ![Omni Chicago Hotel](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/433c2c13_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni Chicago Hotel Downtown Chicago £923 per person 4 May - 8 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,603 reviews) Nice restaurant, attentive staff. Reviewed on 7 Feb 2026 ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Chicago Downtown Chicago £979 per person 16 Apr - 20 Apr found 20 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (3,386 reviews) Spacious and clean room but improvement points on amenities (missing tissue in tissue casing, need to call for amenities, nondairy milk available but not dairy milk, dirty coffee maker cannot make tea), dark, and separate towers inconvenient with friends & availability of lifts during conference season low. Road works and access by car/cab not warned Reviewed on 10 Feb 2026 Don't see what you're looking for? See all available trips from London to Chicago [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-10/2026-03-17/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## FAQs: family holidays in Chicago #### How can I find the best family-friendly holidays in Chicago? At Expedia, it’s super-easy to find family-friendly holidays in Chicago 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 Chicago 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, Chicago family getaways start at £754\. Prices and availability are subject to change and additional terms may apply. #### Can I book an all-inclusive Chicago 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 Chicago and book the whole package in just a few clicks. #### How can I book the best family activity holiday in Chicago? 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 Chicago? To treat the kids to a luxury holiday they’ll never forget, take a look at the most indulgent hotels and resorts in Chicago 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 Chicago family holiday deals? Start by entering your dates, then use the family-friendly filter to narrow down your search to show the best available Chicago 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 Chicago 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 Chicago 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 Chicago in no time. ## Top Kid friendly Chicago Hotels ![Embassy Suites by Hilton Chicago Downtown Magnificent Mile](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown Magnificent Mile 511 North Columbus Drive Chicago IL - 10 min drive from Wrigley Field Stay at this business-friendly hotel in Chicago. Enjoy free breakfast, room service and a fitness centre. Our guests praise the breakfast and the helpful staff ... 8.2/10 Very Good! (2,816 reviews) Room was great, staff was awesome and very helpful. Reviewed on 4 Feb 2026 [](https://expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Palmer House a Hilton Hotel 17 E Monroe St Chicago IL - 12 min drive from Wrigley Field Stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge) and a 24-hour health club. Our guests praise the helpful staff and the ... 8.4/10 Very Good! (2,280 reviews) Clean room, checking in was super easy. Hotel is beautiful and so classy. Reviewed on 7 Feb 2026 [](https://expedia.co.uk/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL - 10 min drive from Wrigley Field Stay at this hotel in Chicago. Enjoy free breakfast, room service and a fitness centre. Our guests praise the breakfast and the pool in their reviews. Popular ... 8.4/10 Very Good! (5,643 reviews) Positives- As my friend said as we went to breakfast “the people here are so nice and look happy to work here!” I agree! Eloisa (I hope that is correct-our bartender ) made happy hour on Friday night even happier! She was friendly and knowledgeable, suggesting drinks we hadn’t had before just by ... Reviewed on 8 Feb 2026 [](https://expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) [See all 5,624 properties in Chicago](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=178248) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ## 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 Chicago ](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[ Chicago Hotels ](https://expedia.co.uk/Chicago-Hotels.d178248.Travel-Guide-Hotels)[ Chicago Holiday Rentals ](https://expedia.co.uk/Chicago-Holiday-Rentals.d178248.Travel-Guide-HolidayRentals)[ Chicago Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chicago.d178248.Car-Hire-Guide)[ Chicago Holidays ](https://expedia.co.uk/Chicago.d178248.Holidays-City-Breaks)[ Things to do in Chicago ](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.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