House Sitting in Woodlawn, 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. 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)"

2. Alexandra

Fun, active sitter for your Pooch!

Near South Side, Chicago, IL, 60616

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

About: My name is Alexandra I am 28 years old. I love movies, animals and live in the South Loop. Recently back in the city I have open availability, expe... (more)

3. 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)"

4. 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)"

5. 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)"

6. Megan

Pets are my life! I love them!

Chicago Lawn, Chicago, IL, 60629

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Megan is a natural with dogs. Both my dogs took an immediate liking in her which always tells me a lot. She went out of her way to accommodate them when we ... (more)"

7. 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)"

8. 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)"

9. Sheila

I'll run with your dog

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Sheila is great with dogs and a wonderful pet owner! She would be a great dog sitter because she takes great care of her pets and would easily extende that c... (more)"

10. 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)"

11. 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)"

12. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

10 repeat clients

"Brittany was so so great! She was extremely flexible, quick to respond, and kept me updated throughout Royal's stay with her. It was clear Brittany was very ... (more)"

Available this weekend
13. Ismael

Experienced dog handler and caring

New City, chicago , IL, 60609

House Sitting, Drop-In Visits, Dog Walking

About: I'm 22 years old I have worked at a dog day care for over 2 years already, I'm flexible with my schedule, I have a car so Transportation wouldn't b... (more)

14. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Emma is the sweetest young woman who truly cares about the well being and happiness of your pet. She asked all the right questions, and followed request. O... (more)"

15. Shantel

I'll show your dog what love is.

South Shore, Chicago, IL, 60649

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

1 repeat client

"Shantel has taken care of my dog for me before. Choosing her to take care of my dog was one of the best decisions I've ever made. She's really responsible an... (more)"

16. Kimberly

Your dog is my dog!

Roseland, Chicago, IL, 60619

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

1 repeat client

"Kimberly is the ultimate dog lover. She cared for her dog Kobe for over 17 years, taking him wherever she went! Kim is responsible, nurturing, and kind which... (more)"

17. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

"I was traveling out of town for two weeks in January and needed a pet sitter. Rebba was an amazing dog sitter to my beloved Mr. Jinx. She sent me daily photo... (more)"

18. Mikayla

Energetic dog-lover

Woodlawn, Chicago, IL, 60637

Dog Boarding, House Sitting, Dog Walking

"Mikayla loves animals, especially dogs. Her fun and cheerful nature attracts dogs to her, and they form an inseparable bond. I couldn't think of a better job... (more)"

19. Breana

Dogs are my favorite people.

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"Breana is excellent with dogs! She is responsible, caring and reliable. She has been around dogs her whole life so she knows how to keep them happy, healthy ... (more)"

20. 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)"

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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.