House Sitting in Woodlawn, Chicago

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

1. Jac

Loving and Experienced Pet Sitter

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Jac did a Sunday to Wednesday home stay with Claudia. I appreciate the quick texts and pictures, thank you! I would recommend Jac to anyone and will certainl... (more)"

2. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Crystals was great. Very responsive when communicating. Very reliable and professional. And Sassy loved her! We hate to leave town, but it's nice to know tha... (more)"

3. Sarah

Will show your pup so much love!!!!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

4. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 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)"

5. Myk'La

Energetic, artsy, happy and caring

Chatham, Chicago, IL, 60619

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)"

6. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

"We LOVE Brittany! She took care of Miko with a lot of love and care while were out on a 14 day trip. She stayed in our house, took care of Miko and our home.... (more)"

7. Kennedi

Love as if it's your own.

Calumet Heights, Chicago , IL, 60619

House Sitting, Drop-In Visits, Dog Walking

About: I was the fortunate ten year old girl, no siblings who grew up with the responsibility of several children ( dogs, frogs, snakes, cats, etc. lol). ... (more)

8. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

"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)"

9. Jordan

Dog Lover and Rescuer

Calumet Heights, Chicago, IL, 60617

House Sitting, Drop-In Visits, Dog Walking

"Jordan is a kind, dedicated woman who gives her all to her passions. Her love of animals is enormous, as is her ability to care for them. She stands out by ... (more)"

10. Grace

Excited to meet your pup!

Woodlawn, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Grace stayed with my dogs over Thanksgiving. They seemed to be happy upon my return. Thanks for taking care of them! (more)"

11. Kimberly

Your dog is my dog!

Roseland, Chicago, IL, 60619

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

1 repeat client

"Kimberly was first responsible for dog sitting my fur baby Sascha during a 2 week honeymoon period. She did an excellent job. My dog (Yorkie) is very parti... (more)"

12. Brittanie

Im friendly energetic and patient

Woodlawn, Chicago , IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"I have a poodle and Brittanie was reccomended to me by a friend I have been using her for up to three years now and she has done plenty of drop ins and walks... (more)"

13. Cheney

It's all about the dogs!

South Chicago, Chicago, IL, 60617

House Sitting, Drop-In Visits, Dog Walking

"Cheney is one of the most caring people I know. She has a deep love for animals, especially dogs. She refers to them as "little people with fur and treats he... (more)"

14. Gabriella

All Dogs go to Heaven.

South Chicago, Chicago, IL, 60617

Dog Boarding, House Sitting

"From the time that I met Gabriella, she's shown that special compassion for animals that only a few have within them. It doesn't surprise me that she is int... (more)"

15. Catalina

Catalina, Dog Lover

Woodlawn, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Catalina has always had a special relationship with dogs. When she was growing up, at various times, she had labradors, neapolitan mastiffs, rottweilers and ... (more)"

16. Martineja

Fun, Comfort, and Love

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"No matter if you need a dog walker or a dog sitter Martineja is the way to go! I was extremely happy with her fast response and she came with treats and toys... (more)"

17. Eva

Lifetime Dog Lover & Future Vet!

Kenwood, Chicago, IL, 60515

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I have known Eva for several of years, we are great friends and there is no other person I would recommend to watch my pet besides her. I would allow her to ... (more)"

18. Janelle

Master's Student and Dog Lover!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

About: I have experience taking care of dogs large and small, the fierce and the sweethearts. I was raised with king size German Shepherds and dog-sat and... (more)

19. Leolin

Responsible animal lover!!

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"I've known Leolin for 10 years and can attest to her love for animals. She is a vegan, which is something that is very important to her and reflects the resp... (more)"

20. Michaela

Fun, creative, pup loving gal!

Kenwood, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Michaela Is great! She took wonderful care of my dog and cat and they were very content when we arrived home after a whole week. She kept me up to date on ... (more)"

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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.

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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.