Title: Far Southwest Side Pet-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 Pet-friendly Holidays ## Book a Pet-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 + Pet-friendly hotel deals 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 £803 per person 12 Mar - 16 Mar found 24 hours ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Everything and everyone was amazing definitely recommend Reviewed on 10 Feb 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 £1,063 per person 12 Mar - 16 Mar found 24 hours ago Return direct flight included Dublin (DUB) 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 £1,267 per person 4 May - 8 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 ![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 £864 per person 12 Mar - 16 Mar found 24 hours ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9/10 Wonderful! (380 reviews) My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone! Reviewed on 2 Feb 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago £977 per person 12 Mar - 16 Mar found 24 hours ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (3,392 reviews) Clean rooms, great reception, and beautiful views! Reviewed on 10 Feb 2026 Don't see what you're looking for? See all available trips from Dublin to Far Southwest Side [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) ## 5\* Pet-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 £1,063 per person 12 Mar - 16 Mar found 24 hours ago Return direct flight included Dublin (DUB) 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 £1,267 per person 4 May - 8 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 ![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 £1,606 per person 4 May - 8 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Gorgeous property, facilities, and location. Reviewed on 6 Feb 2026 Don't see what you're looking for? See all available trips from Dublin to Far Southwest Side [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 Pet-friendly 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 £790 per person 23 Mar - 26 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Everything and everyone was amazing definitely recommend Reviewed on 10 Feb 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 £1,026 per person 23 Mar - 26 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Lovely room. Excellent staff. Reviewed on 3 Feb 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 £849 per person 23 Mar - 26 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (380 reviews) My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone! 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/2026-03-10/2026-03-17/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Pet-friendly 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 £803 per person 12 Mar - 16 Mar found 24 hours ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Everything and everyone was amazing definitely recommend Reviewed on 10 Feb 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 £1,063 per person 12 Mar - 16 Mar found 24 hours ago Return direct flight included Dublin (DUB) 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 £1,267 per person 4 May - 8 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 Don't see what you're looking for? See all available trips from Dublin to Far Southwest Side [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) ## How to find a pet-friendly holiday in Far Southwest Side #### How can I book the best pet-friendly holidays in Far Southwest Side? As a pet parent, you want your best bud along for your Far Southwest Side holiday, right? So use our pet-friendly filter to find all the places that are purr-fect for cats, dogs or even well-trained rabbits. Think stacks of outside space, welcome treats and maybe something lovely that keeps the travel time to a minimum. #### Can I book a cheap Far Southwest Side pet-friendly holiday? pet-friendly package holidays start at £790, but prices and availability are subject to change, and additional terms may apply. To narrow down the best deals, sort by price and use the filters to find cheap places with tail-wag-worthy amenities. #### How can I book holiday lets in Far Southwest Side that are pet friendly? The space and seclusion of a holiday let is great for holidaying as a family or bigger group, and if your furry friends are with you, even better. Use both the private holiday home and pet-friendly filters to find all the options that tick both boxes. #### How can I find pet-friendly holidays in Far Southwest Side with hot tubs? Pet-friendly holidays aren’t just about the animals – you deserve to indulge yourself, too! Filter our Far Southwest Side properties using the hot-tub and pet-friendly holiday options and find somewhere you can relax while the pooches snooze. #### Can I book a pet-friendly holiday in Far Southwest Side with a car? For hassle-free pet-friendly travel, a car is a no-brainer. Book both your car hire and accommodation with Expedia and you’ll sniff out some great savings. #### How can I book last-minute pet-friendly holidays in Far Southwest Side? A spontaneous last-minute getaway to Far Southwest Side with your pet is what holiday dreams are made of. You might even dig up discounted rates on some hotels by booking close to the date. #### Can I book a pet-friendly holiday in Far Southwest Side with free cancellation and/or flexible dates? We offer several places to stay with free cancellation in Far Southwest Side, just use the fully refundable filter to find the ones available on your dates. Make sure you read the terms and conditions, too. #### Why should I book Far Southwest Side pet-friendly travel with Expedia? Thanks to our dedicated pet-friendly filter, it’s incredibly easy to find accommodation in Far Southwest Side that welcomes fur babies. Search, choose and book in just a few clicks. Purr-fect! ## 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 Pet-friendly Holiday Destinations > - [Pet Friendly Holidays in Cornwall ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/10558/Cornwall) > - [Pet Friendly Holidays in Devon ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/181736/Devon) > - [Pet Friendly Holidays in Dorset ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/184046/Dorset) > - [Pet Friendly Holidays in France ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/59/France) > - [Pet Friendly Holidays in Great Yarmouth ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/4647/Great-Yarmouth) > - [Pet Friendly Holidays in Ireland ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/84/Ireland) > - [Pet Friendly Holidays in Newquay ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/2596/Newquay) > - [Pet Friendly Holidays in Norfolk ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/6046223/Norfolk) > - [Pet Friendly Holidays in Northern Ireland ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/11221/Northern-Ireland) > - [Pet Friendly Holidays in Northumberland ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/6046225/Northumberland) > - [Pet Friendly Holidays in Scotland ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/11219/Scotland) > - [Pet Friendly Holidays in Skegness ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/6048672/Skegness) > - [Pet Friendly Holidays in Somerset ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/6940/Somerset) > - [Pet Friendly Holidays in Suffolk ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/6981/Suffolk) > - [Pet Friendly Holidays in the Isle Of Wight ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/6046218/Isle-Of-Wight) > - [Pet Friendly Holidays in the United Kingdom ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/190/United-Kingdom) > - [Pet Friendly Holidays in Wales ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/3754/Wales) > - [Pet Friendly Holidays in Weymouth ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/5470/Weymouth) > - [Pet Friendly Holidays in Yorkshire ](https://www.expedia.co.uk/lp/theme-holidays/pet-friendly-holidays/6342462/Yorkshire) ## 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