Pet Friendly Holiday Rentals in Chicago, IL

This 2-bedroom apartment in Chicago allows 2 dogs of any size for an additional fee of $20 per pet, per night. Cats may also be allowed by request.

This 1-bedroom apartment in Chicago allows dogs for an additional fee of $25 per pet, per month. There is also a one-time fee of $500 per stay. Cats may also be allowed by request, but all pets must be approved in advance. Breed and size restrictions may apply.

This apartment in Chicago allows 1 dog of any size for an additional fee of $15 per night. Cats are also welcome. Breed restrictions may apply.

This 1-bedroom vacation rental in chicago allows dogs of any size for an additional fee of $15 per pet, per night. Sorry, no cats.

This 2-bedroom vacation rental in Chicago allows 2 dogs of any size for an additional fee of $20 per pet, per night. Sorry, no cats. Pet bowls and a bed are provided. The yard is fenced.

This house in Chicago allows pets of any size for an additional fee. Both dogs and cats are welcome.

This 2-bedroom condo in Chicago allows dogs of any size for an additional fee. Cats may also be allowed by request.

This 3-bedroom cottage in Chicago allows pets of any size for an additional fee. Both dogs and cats are welcome.

This flat in Chicago allows pets of any size for an additional fee. Both dogs and cats are welcome.

This 1-bedroom apartment in Chicago allows 1 dog of any size for an additional fee of $15 per night. Cats are also welcome. There is an on-site dog park and designated dog walking areas on the property. Breed restrictions may apply.

This 3-bedroom apartment in Chicago allows 1 dog of any size for an additional fee of $15 per night. Cats are also welcome. There is an on-site dog park and designated dog walking area. Breed restrictions may apply.

This flat in Chicago allows pets of any size for an additional fee of $50 per pet, per stay. Both dogs and cats are welcome, but exotic pets are not allowed.

This condo in Chicago allows pets of any size for an additional fee. Both dogs and cats are welcome.

This flat in Chicago allows pets of any size for an additional fee of $50 per pet, per stay. Both dogs and cats are welcome, but exotic pets are not allowed.

This flat in Chicago allows pets of any size for an additional fee of $50 per pet, per stay. Both dogs and cats are welcome, but exotic pets are not allowed.

This 2-bedroom apartment in Chicago allows 1 dog of any size for an additional fee of $15 per night. Cats are also welcome. There is an on-site dog park and designated dog walking area. Breed restrictions may apply.

Pet policies are determined by the individual owner of each Vrbo property. For more information on the pet fee, weight limit and other restrictions at a dog-friendly Vrbo in Chicago, please contact the owner directly or read the 'House Rules' section of their listing. Also be sure to include your pet(s) in the 'Guest' field when making your reservation, so the pet fee can be included. If applicable, it will be usually be displayed in the 'On-site Fees' or 'Owner Fees' sections during checkout. Some owners will also wait until you arrive in Chicago to collect the pet fee.

This flat in Chicago allows pets of any size for an additional fee of $50 per pet, per stay. Both dogs and cats are welcome, but exotic pets are not allowed.

This flat in Chicago allows pets of any size for an additional fee of $50 per pet, per stay. Both dogs and cats are welcome, but exotic pets are not allowed. Please note that pets cannot be left unattended.