Pet Friendly Vacation Rentals in Chicago, IL

There are 138 pet friendly vacation rentals in Chicago, IL. Need help deciding where to stay with your dog? You can browse the results below, use our filter to search by amenities, or call 877-411-FIDO to have our Canine Concierge help you choose the perfect spot. All pet policy information is guaranteed and there are no booking fees!

Pet Friendly Relaxed Bucktown Apartment in Chicago, IL
This 1-bedroom Airbnb rental in Chicago welcomes two dogs of any size for no additional fee. Exceptions may be made for more than two small pets with prior homeowner approval. Pets left alone in the apartment must be accustomed to being unattended in an unfamiliar environment, and preferably crated.
Pet Friendly Stunning Chicago Loft in Chicago, IL
This one-bedroom Airbnb rental in Chicago welcomes one dog up to 40 lbs for an additional fee of $75 per stay. Cats are not permitted.
Pet Friendly Modern Boystown/Wrigleyville 1 BDRM in Chicago, IL
Dogs are allowed at this 1-bedroom Airbnb rental in Chicago (if they get along well with other pets). Please contact Michael for more details on the pet fee, weight limit, and any other restrictions prior to booking.
Pet Friendly 2BD Suite @ The Guesthouse Hotel in Chicago, IL
Pets are allowed at this 2-bedroom Airbnb rental in Chicago. Please contact Rick for more details on the pet fee, weight limit, and any other restrictions prior to booking.
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