Title: Chicago Pet-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 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 Chicago Price found within the past 48 hours. Click for updated prices. ![Kimpton Gray Hotel by IHG](https://images.trvl-media.com/lodging/14000000/13360000/13351500/13351499/14bf852a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Gray Hotel by IHG Downtown Chicago £943 per person 16 Apr - 20 Apr found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,003 reviews) Wonderful hotel to stay at. Located right downtown and a close walk to everything. Loved the complimentary cocktail hour too! Reviewed on 23 Feb 2026 ![Staypineapple, An Iconic Hotel, The Loop](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/eac2e31f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Staypineapple, An Iconic Hotel, The Loop Downtown Chicago £1,059 per person 17 Apr - 22 Apr found 1 day ago Return flight included Dublin (DUB) to Chicago (ORD) 9.4/10 Exceptional! (1,003 reviews) Everything was nice and clean. The incidentals charge wzs $58 for bottled water and cellophane wrapped cookies. That was a surprise at the end of stay. Reviewed on 28 Feb 2026 ![Kinzie Hotel](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/6044b661_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kinzie Hotel Downtown Chicago £1,017 per person 20 May - 24 May just found Return flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,993 reviews) Very courteous and super helpful staff. Reviewed on 2 Mar 2026 ![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Virgin Hotels Chicago Downtown Chicago £1,067 per person 20 May - 24 May just found Return flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,404 reviews) We chose this hotel for my husband’s birthday weekend. The room was spacious clean and trendy. The bed was so comfortable. The happy hour was excellent and the game room and bar on the second floor was fabulous. The customer service was phenomenal. They surprised my husband with a goody bag for his birthday which was the icing on the cake. The hotel is currently undergoing renovations but it was still a great stay. Reviewed on 3 Mar 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 £1,090 per person 24 May - 29 May found 1 day ago Return flight included London (LON) to Chicago (ORD) 8.6/10 Excellent! (2,655 reviews) Hotel was really nice and super clean. Staff were amazing. Reviewed on 3 Mar 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/2026-04-04/2026-04-11/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Pet-friendly holidays in Chicago Price found within the past 48 hours. Click for updated prices. ![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Virgin Hotels Chicago Downtown Chicago £700 per person 29 Apr - 2 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,404 reviews) We chose this hotel for my husband’s birthday weekend. The room was spacious clean and trendy. The bed was so comfortable. The happy hour was excellent and the game room and bar on the second floor was fabulous. The customer service was phenomenal. They surprised my husband with a goody bag for his birthday which was the icing on the cake. The hotel is currently undergoing renovations but it was still a great stay. Reviewed on 3 Mar 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 £737 per person 29 Apr - 2 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 8.6/10 Excellent! (2,655 reviews) Hotel was really nice and super clean. Staff were amazing. Reviewed on 3 Mar 2026 ![L7 Chicago by LOTTE](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/6dfbfa42_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### L7 Chicago by LOTTE Downtown Chicago £779 per person 29 Apr - 2 May found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.6/10 Exceptional! (3,227 reviews) Clean room, friendly and helpful staff. Great location for walkable dining destinations. Great restaurant, Perilla is an exceptional Korean Steakhouse had terrific meal for 5 people. I have stayed here before and will come back. Reviewed on 2 Mar 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/2026-04-04/2026-04-11/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Pet-friendly holidays in Chicago Price found within the past 48 hours. Click for updated prices. ![Kimpton Gray Hotel by IHG](https://images.trvl-media.com/lodging/14000000/13360000/13351500/13351499/14bf852a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Gray Hotel by IHG Downtown Chicago £943 per person 16 Apr - 20 Apr found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,003 reviews) Wonderful hotel to stay at. Located right downtown and a close walk to everything. Loved the complimentary cocktail hour too! Reviewed on 23 Feb 2026 ![Kinzie Hotel](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/6044b661_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kinzie Hotel Downtown Chicago £1,017 per person 20 May - 24 May just found Return flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,993 reviews) Very courteous and super helpful staff. Reviewed on 2 Mar 2026 ![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Virgin Hotels Chicago Downtown Chicago £1,067 per person 20 May - 24 May just found Return flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,404 reviews) We chose this hotel for my husband’s birthday weekend. The room was spacious clean and trendy. The bed was so comfortable. The happy hour was excellent and the game room and bar on the second floor was fabulous. The customer service was phenomenal. They surprised my husband with a goody bag for his birthday which was the icing on the cake. The hotel is currently undergoing renovations but it was still a great stay. Reviewed on 3 Mar 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/2026-04-04/2026-04-11/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## How to find a pet-friendly holiday in Chicago #### How can I book the best pet-friendly holidays in Chicago? As a pet parent, you want your best bud along for your Chicago 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 Chicago pet-friendly holiday? pet-friendly package holidays start at £700, 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 Chicago 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 Chicago with hot tubs? Pet-friendly holidays aren’t just about the animals – you deserve to indulge yourself, too! Filter our Chicago 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 Chicago 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 Chicago? A spontaneous last-minute getaway to Chicago 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 Chicago with free cancellation and/or flexible dates? We offer several places to stay with free cancellation in Chicago, 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 Chicago pet-friendly travel with Expedia? Thanks to our dedicated pet-friendly filter, it’s incredibly easy to find accommodation in Chicago that welcomes fur babies. Search, choose and book in just a few clicks. Purr-fect! ## Top Pet-friendly Chicago Hotels ![The Royal Sonesta Chicago River North](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/20c3f16a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Royal Sonesta Chicago River North 505 N State Street Chicago IL - 10 min drive from Wrigley Field Stay at this luxury hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and valet parking (surcharge). Our guests praise the pool and the restaurant ... 9.2/10 Wonderful! (2,456 reviews) Amazing hotel! Close to every store you’ll ever need during your stay. Reviewed on 2 Mar 2026 [](https://expedia.co.uk/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.Hotel-Information) ![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Virgin Hotels Chicago 203 N Wabash Ave Chicago IL - 11 min drive from Wrigley Field Stay at this luxury hotel in Chicago. Enjoy free Wi-Fi, a nightclub and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in their reviews. ... 9.2/10 Wonderful! (1,408 reviews) We chose this hotel for my husband’s birthday weekend. The room was spacious clean and trendy. The bed was so comfortable. The happy hour was excellent and the game room and bar on the second floor was fabulous. The customer service was phenomenal. They surprised my husband with a goody bag for his ... Reviewed on 3 Mar 2026 [](https://expedia.co.uk/Chicago-Hotels-Sports-Illustrated-Resorts-Chicago.h9119528.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago 720 S Michigan Ave Chicago IL - 13 min drive from Wrigley Field Stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge) and a health club. Our guests praise the helpful staff and the clean rooms ... 8.6/10 Excellent! (2,660 reviews) Hotel was really nice and super clean. Staff were amazing. Reviewed on 3 Mar 2026 [](https://expedia.co.uk/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) [See all 5,650 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 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 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