House Sitting in Kenwood, Chicago

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Catherine did an exceptional job dog sitting. I came home to a happy dog and my house in the same condition I left it in. Thank you so much!! (more)"

2. Aasha

I'm a dog loving recent graduate!

Near West Side, Chicago , IL, 60661

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Aasha took really good care of Luna! I came home to a napping puppy. She send me updates every once in a while. She is really nice and responsible. I already... (more)"

3. Kat

Quality care for our fur babies

Lower West Side, Chicago , IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Kat has been the best dog sitter I have came across. It is most important for me to find a trustworthy, responsible and friendly person, and Kat is exactly t... (more)"

4. Sidney

Experienced & Active Dog Enthusiast

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Sidney was great with our dog! She was able to come last minute and kept him happy! She even came with some treats for him. We will reach out to her again. (more)"

5. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

17 repeat clients

"Penelope took great care of Britney- she sent updates and photos which were much appreciated. My apartment was left spotless, I will definitely use her again! (more)"

6. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Collin is my first experience with Rover and I couldn't be more pleased. Using Rover came with short notice and I worried that would create a problem. Coll... (more)"

7. Kate

Experienced Dog Lover!!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Katie was wonderful- Major loved her, possibly more than me now. Will work with her again! (more)"

8. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Our girls loved Krystina from the moment they met her, and from the pictures she sent they seemed happy with her services. She was nice, caring, and flexible. (more)"

9. Allison

Certified Veterinary Technician

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits

5 repeat clients

"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)"

10. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Another great sleepover for Sassy with Crystal! We called last minute for an unexpected trip and as usual, she came through for us and was exceptional. On ... (more)"

11. Hayley

Flexible, reliable, and available!

Bridgeport, Chicago , IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"My wife and needed some help with our pooches when we were in the hospital welcoming our daughter. Hayley met us the night before my wife went to labor, and ... (more)"

12. Christina

Calm, warm hearted dog lover

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Christina took excellent care of my pup while I was away for a long weekend. She communicated regularly and handled small requests, no problem! Will definite... (more)"

Available this weekend
13. Myk'La

Mind, face, and soul of a pup

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Myk'La is a awesome person and some one i'd highly recommended for the Dog Caregiver position.She posess a high spirit personality along with an outgoing and... (more)"

14. Zoe

Experienced and enthusiastic

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Zoe has dog sat for our 3 large dogs on 4 occasions of varying lengths of time. She is a true animal lover! Zoe's experience with dogs, her willingness to ge... (more)"

15. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"Our experience with LeAnna was wonderful! She took perfect care of our dog and cat and kept us updated throughout the stay. She really listened and We are co... (more)"

16. Alexandra

Loving sitter in the city.

Bridgeport, Chgo, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

18 repeat clients

"Alexandra did a great job with our dog Blaze. This was our first extended trip away from our rescue dog and she made us feel that we were leaving her in cap... (more)"

17. Eleanor

Because it really is my pleasure :)

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Eleanor did a great job watching Buddha and my home while away on business. She was very communicative and sent a bunch of pictures along with her texts. I t... (more)"

18. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

10 repeat clients

"Brittany is a CHAMP. She's a savvy handler and trainer who communicated well, followed instructions perfectly, navigated both our dog's behavioral issues and... (more)"

19. Sarah

Will show your pup so much love!!!!

Bridgeport, Chicago, IL, 60608

House Sitting

2 repeat clients

"Sarah is a loving, enthusiastic dog caregiver who I have trusted with my beloved French Bulldog, Pablo several times in the past. She is very responsible an... (more)"

20. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"I highly recommend Emma. Our household is big and crazy and she held her own :-) She sent lots of pictures and updates so we didn't have to worry about our k... (more)"

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Learn About Premier

Home owners love Chicago house sitters on Rover. 9,532 owners have reviewed sitters in the Chicago, IL metro area, giving them an average rating of 4.9/5.

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.