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. ![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 £654 per person 5 Mar - 9 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Great location! Very helpful staff! Reviewed on 22 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 Save 100% on your flight £1,142 per person 30 Jan - 5 Feb found 11 hours ago Return flight included London (LCY) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Loved it here and would stay again! Everything was perfect! Reviewed on 21 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 £1,331 per person 30 Jan - 5 Feb found 11 hours ago Return flight included London (LCY) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Service and clean room - paying attention to the details Reviewed on 22 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 £654 per person 5 Mar - 9 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Great location, clean room and friendly staff! Reviewed on 14 Dec 2025 ![Chicago Athletic Association, a Hyatt Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/6b24bc12_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chicago Athletic Association, a Hyatt Hotel Downtown Chicago £715 per person 30 Jan - 5 Feb found 11 hours ago Return flight included London (LCY) to Chicago (ORD) 9/10 Wonderful! (1,002 reviews) Simply, amazing stay. Reviewed on 21 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/2026-01-23/2026-01-30/?FromAirport=LON&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 Save 100% on your flight £1,142 per person 30 Jan - 5 Feb found 11 hours ago Return flight included London (LCY) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Loved it here and would stay again! Everything was perfect! Reviewed on 21 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 £1,331 per person 30 Jan - 5 Feb found 11 hours ago Return flight included London (LCY) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Service and clean room - paying attention to the details Reviewed on 22 Dec 2025 ![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 £1,151 per person 18 Mar - 22 Mar found 12 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Langham is always a superior stay Reviewed on 1 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/2026-01-23/2026-01-30/?FromAirport=LCY&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. ![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 £495 per person 30 Jan - 2 Feb found 12 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Aisha, Diamond and Natalie at thr front desk are always so incredibly helpful and accommodating. This is my favorite place to stay in downtown Chicago. Fabulous views. Full kitchen. Washer/dryer. Balcony. Best of Chicago! Truly Reviewed on 15 Dec 2025 ![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 £752 per person 4 Feb - 7 Feb found 3 hours ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Courteous staff. Very clean rooms. Excellent location. Breakfast was wonderful (line starts forming around 9am). Self park nearby. Reasonably priced. Reviewed on 22 Dec 2025 ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago O'Hare Airport O'Hare £873 per person 4 Feb - 7 Feb found 3 hours ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 8.2/10 Very Good! (2,158 reviews) It was smooth and very kind Reviewed on 17 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/2026-01-23/2026-01-30/?FromAirport=LHR&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. ![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 £654 per person 5 Mar - 9 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Great location, clean room and friendly staff! Reviewed on 14 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 £875 per person 5 Mar - 9 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Loved it here and would stay again! Everything was perfect! Reviewed on 21 Dec 2025 ![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 £789 per person 12 Mar - 16 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Courteous staff. Very clean rooms. Excellent location. Breakfast was wonderful (line starts forming around 9am). Self park nearby. Reasonably priced. Reviewed on 22 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/2026-01-23/2026-01-30/?FromAirport=LON&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 £495, 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