House Sitting in Kenwood, Chicago

Find a loving dog sitter to watch your dog overnight in your home.

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1. TIANJIAO

Ariel's Dog Haven

Kenwood, CHICAGO, IL, 60615

Dog Boarding, House Sitting

"This is our second time booking Ariel and we will continue to use her for all of our house-sitting needs. She is so great at sending updates and pictures at ... (more)"

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2. Elijah

Dog lover

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Elijah has watched and walked my dog, Skip, for the past year. He is beyond attentive to Skip and now whenever the doorbell rings Skip goes bounding towards ... (more)"

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3. Kat

Recent grad who LOVES DOGS

Kenwood, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: None (more)

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4. David

Caring for other's dogs since 1990

Bridgeport, CHICAGO, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"David is great. It is obvious that he loves animals. We were very comfortable having David stay at our place and watch our two dogs. He communicated well ... (more)"

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5. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Rebba is incredibly compassionate and loving with dogs. She genuinely cares for them and showed great kindness and care for my late dog. Your dog will be i... (more)"

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6. Morgan

Time for long walks - dog lover

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Morgan was absolutely fantastic with our animals. We are so grateful to her for taking such great care of them and taking care of our home as well. We will d... (more)"

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7. Katja

Over 10 years of dog experience!

Grand Boulevard, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

"Thank you again for taking care of our pets. You are definitely a trusted person when it comes to caring for our pets while house sitting. I highly recommend... (more)"

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8. Sarah

Grad student seeking furry friends

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Sarah is a responsible person who grew up with both large and small dogs and she has always given them the best care. I can guarantee your dog will receive l... (more)"

Confirmed availability
Thanksgiving
9. Sam

Basically Raised by Dogs.

Bridgeport, CHICAGO, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"Sam would be perfect for this job. He is so easy to get along with. He is patient, kind trustworthy and very reliable. These are all qualities I look for in ... (more)"

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10. Zak

Home all day - fenced yard

Douglas, Chicago, IL, 60616

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: None (more)

Confirmed availability
This weekend
11. Jasmine

I have a great deal of free time

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"For as long as I've known Jasmine, she has always been loving and caring toward dogs. She goes out of her way to show compassion to the dogs she interacts wi... (more)"

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12. Allison

Certified Veterinary Technician

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits

"Allison is hands down the best pet sitter! We had her stay in our home over a long weekend with our two senior pups. She provided excellent communication and... (more)"

13. Jennifer

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Jennifer took great care of my two dogs. She even agreed to extend her stay an extra day on short notice. The boys got a lot of exercise and the apartment wa... (more)"

14. Zachary

Zach's Hyde Park Dog-Care

South Side, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

"Zachary house sits for my 3 very busy dogs. He is reliable & extremely responsible in keeping them on feeding and walking schedules. He also checks in with m... (more)"

15. Rachel

No longer accepting work!

Douglas, Chicago, IL, 60609

House Sitting

"Cooper's a lot of work - he needs a lot of attention and playtime, and Rachel was great with him! Will definitely reach out to Rachel the next time I'm in to... (more)"

16. Masha

Home full time - Great with animals

Douglas, Chicago, IL, 60616

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Hello pet parents, I’m writing on behalf of Masha S. to reassure you that your animals will be in the best of hands. I’ve known Masha for a little over two ... (more)"

Confirmed availability
Thanksgiving
17. Danielle

Dog sitter available for your pup!

Washington Park, Chicago, IL, 60615

House Sitting, Dog Walking

"Danielle is a deeply caring spirit; other people's pets take a shine to her immediately because she exudes a calming yet friendly and engaging aura. Danielle... (more)"

Confirmed availability
Thanksgiving
18. Khala

Always available! Always flexible!

Woodlawn, Chicago, IL, 60637

Dog Boarding, House Sitting, Doggy Day Care

"Khala has been taking care of my pug, Lily Grace, for three years. I trust her completely. Although when I come to pick Lily Grace up, she doesn't always w... (more)"

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19. Grace

Caring evening/weekend sitter!

Kenwood, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Grace is great and a responsible and playful dog caregiver. She was very dependable and took great care of our very active terrier!. Five Stars! (more)"

Confirmed availability
Thanksgiving
20. Mathilde

Happy to run, walk, or meander!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Mathilde would by far be the first person i know that i would trust our beloved family dog with. She is an extremely responsible, kind and caring person. ... (more)"


The next time you head out of town and need someone to take care of your pet - and your home - turn to Rover for your house sitting needs. It's easy to find a loving pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover - it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy house sitters for your pets--and avoid the kennel.

Want to learn more? Check out reviews from pet owners who have used Rover.