Title: Southern Wisconsin Kid friendly Holidays 2025/2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/6068277/f9df43ae-9037-4ed0-8755-204129016a40.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southern Wisconsin Kid friendly Holidays ## Book a Kid friendly Hotel + Flight or Car together to unlock savings Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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 Southern Wisconsin 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 £696 per person 27 Nov - 2 Dec found 24 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) I loved the hotel, however I would request an inside room next time. It was extremely noisy outside. Reviewed on 11 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-27/2025-12-02/?FromAirport=DUB&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=MotUKBI57nsd6BCPXXeYV5kdBikBEgi9bo-9VGpUJKUb8_tyGTHsut-7QOFfYU-K) ![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 £1,108 per person 27 Nov - 2 Dec found 24 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Everything was great Reviewed on 12 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-27/2025-12-02/?FromAirport=DUB&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=MotUKBI57nsd6BCPXXeYV5kdBikBEgi9bo-9VGpUJKUmJrCcEfz2k2sBDDefvx1p) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago £1,296 per person 27 Nov - 2 Dec found 24 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better. Reviewed on 14 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-27/2025-12-02/?FromAirport=DUB&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=MotUKBI57nsd6BCPXXeYV5kdBikBEgi9bo-9VGpUJKUBoiOaXmfLeCqeWj8s-EYT) ![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 £907 per person 25 Nov - 1 Dec found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (698 reviews) Property was as it was shown in the pictures. Clean and spacious. Also very easy walk to lots of restaurants and other tourist spots. Would stay again. Reviewed on 13 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-25/2025-12-01/?FromAirport=LON&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=74500458&paandie=true&HotelClass=40&dealMarker=UXr9cxJbxmXZCbSgRrTFTLMdZTlVZMe5SLWVqJELzdTBeYlA9yrboLE6o-2tdTzt) ![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 £731 per person 27 Nov - 2 Dec found 24 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.2/10 Wonderful! (1,222 reviews) I stayed here for one night for business travel. The room was huge. Great mini bar options. I had a nice breakfast at the restaurant. Reviewed on 10 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-27/2025-12-02/?FromAirport=DUB&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=MotUKBI57nsd6BCPXXeYV5kdBikBEgi9bo-9VGpUJKVHctif4rz2P4F5YkWpw3w1) Don't see what you're looking for? See all available trips from Dublin to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=DUB&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Kid friendly holidays in Southern Wisconsin 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 £1,108 per person 27 Nov - 2 Dec found 24 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Everything was great Reviewed on 12 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-27/2025-12-02/?FromAirport=DUB&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=MotUKBI57nsd6BCPXXeYV5kdBikBEgi9bo-9VGpUJKUmJrCcEfz2k2sBDDefvx1p) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago £1,296 per person 27 Nov - 2 Dec found 24 hours ago Return flight included Dublin (DUB) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better. Reviewed on 14 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-27/2025-12-02/?FromAirport=DUB&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=MotUKBI57nsd6BCPXXeYV5kdBikBEgi9bo-9VGpUJKUBoiOaXmfLeCqeWj8s-EYT) ![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/a9b39b37_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Art Villa West Town Save 100% on your flight £1,171 per person 25 Nov - 1 Dec found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 10/10 Exceptional! (2 reviews) [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-25/2025-12-01/?FromAirport=LON&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&HotelClass=50&dealMarker=rGUFe02-_Ab7fN77Q3G2LFPaSxdQeANRaqrbZKxlb-vNb02ia0qmH7GVNd3PgLwM) Don't see what you're looking for? See all available trips from Dublin to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=DUB&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Kid friendly holidays in Southern Wisconsin 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 £674 per person 16 Nov - 19 Nov found 19 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) I loved the hotel, however I would request an inside room next time. It was extremely noisy outside. Reviewed on 11 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-16/2025-11-19/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=_F3XtwqJjczNu1YTkSq1xmEnuckl-ANcmoz8p_JRhPil7TD7Cw8-D-jt4l2RRL3a) ![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 £872 per person 16 Nov - 19 Nov found 19 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Everything was great Reviewed on 12 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-16/2025-11-19/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=_F3XtwqJjczNu1YTkSq1xmEnuckl-ANcmoz8p_JRhPhELuIC4FbaDpV72J6JIl46) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago £939 per person 16 Nov - 19 Nov found 1 hour ago Return direct flight included London (LHR) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better. Reviewed on 14 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-16/2025-11-19/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=t-s0udwzxCZ1aB60bCslRG3TJE1UW_TI58b3D0iUkec5a-Y-tPnZE1TyIdtdizQx) Don't see what you're looking for? See all available trips from London to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Kid friendly holidays in Southern Wisconsin 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 £790 per person 20 Nov - 24 Nov found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,222 reviews) I stayed here for one night for business travel. The room was huge. Great mini bar options. I had a nice breakfast at the restaurant. Reviewed on 10 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-20/2025-11-24/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=OWBfzzOkUIZbu4Q2F5nRpNMARgRRJUgmwXhnmMIrZRu0YyiJCx0nX_JDAb9ZBDDd) ![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 £1,072 per person 27 Dec - 31 Dec found 20 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Everything was great Reviewed on 12 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-27/2025-12-31/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=FWFmHZitwb-cO3vULTjwWLZeQxtHPpjKGKOG2g-yeWiOXm1Q4d2wWzqktwtNJcki) ![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 £840 per person 17 Nov - 21 Nov found 2 hours ago Return direct flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (698 reviews) Property was as it was shown in the pictures. Clean and spacious. Also very easy walk to lots of restaurants and other tourist spots. Would stay again. Reviewed on 13 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-17/2025-11-21/?FromAirport=LON&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=74500458&paandie=true&dealMarker=Vk5nqoznAJ9PCpHTBklWqHuDzV9OSB5sKzfh75lBUpi0Q40OoeC5tNZCNk9nd6aB) Don't see what you're looking for? See all available trips from London to Southern Wisconsin [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2025-11-14/2025-11-21/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## FAQs: family holidays in Southern Wisconsin #### How can I find the best family-friendly holidays in Southern Wisconsin? At Expedia, it’s super-easy to find family-friendly holidays in Southern Wisconsin 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 Southern Wisconsin 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, Southern Wisconsin family getaways start at £674. Prices and availability are subject to change and additional terms may apply. #### Can I book an all-inclusive Southern Wisconsin 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 Southern Wisconsin and book the whole package in just a few clicks. #### How can I book the best family activity holiday in Southern Wisconsin? 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 Southern Wisconsin? To treat the kids to a luxury holiday they’ll never forget, take a look at the most indulgent hotels and resorts in Southern Wisconsin 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 Southern Wisconsin family holiday deals? Start by entering your dates, then use the family-friendly filter to narrow down your search to show the best available Southern Wisconsin 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 Southern Wisconsin 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 Southern Wisconsin 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 Southern Wisconsin 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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[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 Southern Wisconsin](https://expedia.co.uk/Cheap-Flights-To-Southern-Wisconsin.d553248635975749457.Travel-Guide-Flights)[Southern Wisconsin Hotels](https://expedia.co.uk/Southern-Wisconsin-Hotels.d553248635975749457.Travel-Guide-Hotels)[Southern Wisconsin Holiday Rentals](https://expedia.co.uk/Southern-Wisconsin-Holiday-Rentals.d553248635975749457.Travel-Guide-HolidayRentals)[Southern Wisconsin Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southern-Wisconsin.d553248635975749457.Car-Hire-Guide)[Southern Wisconsin Holidays](https://expedia.co.uk/Southern-Wisconsin.d553248635975749457.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. 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