House Sitting in 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. Bri

Student wanting all your dogs love

Loop, Chicago, IL, 60605

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

"Bri was amazing with our Australian Shepherd!! She took him out to play and go potty more times than we asked for and she always made sure he was very well t... (more)"

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2. Angelica

Home full-time, flexible schedule.

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Angelica was great! She was so sweet with Henry and sent us pictures and updates throughout the evening. We will definitely have her back again! (more)"

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3. Presley

lifelong pet owner; home full-time

Near South Side, Chicago, IL, 60605

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

"Presley was a terrific sitter! Jordy had some anxiety issues the first night and Presley was very patient and understanding of his situation. She even resear... (more)"

Confirmed availability
This weekend
4. Gray

Will walk and care for dogs!

West Town, Chicago, IL, 60622

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

"Gray was a fantastic sitter for Jordy! He provided great communication and photos throughout the stay, he was patient when Jordy had some anxiety issues and ... (more)"

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5. Imani

Dogs are friends not food!

Lower West Side, CHICAGO, IL, 60608

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

"Imani was wonderful. She put us at ease that our cat and dog were well taken care of, and gave us updates throughout our trip without making us feel like we ... (more)"

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6. Mariah

In love with all furbabies

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Mariah watched our puppy for us on Thanksgiving. She was wonderful! She came over a few days prior to meet us and our dog; which I loved. She was kind, punct... (more)"

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7. Reese

College Student - Lots of Free Time

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits

"Reese is very kind and thoughtful. She is also get back to you asap when planning a sitting. Is also very flexible scheduling around your needs. Highly r... (more)"

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8. TIANJIAO

Ariel's Dog Haven

Loop, CHICAGO, IL, 60605

Dog Boarding, House Sitting, Drop-In Visits

"Ariel was fantastic with Ruby and really was able to get her what she needs - lots of exercise! We came home to a happy and healthy pup. We felt at ease know... (more)"

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9. Jonathan

I watch your pets so you can relax!

Loop, Chicago, IL, 60602

House Sitting, Drop-In Visits, Dog Walking

"Great! (more)"

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10. Kenzi

I can run, play, and walk your dog!

South Lawndale, chicago, IL, 60623

House Sitting, Drop-In Visits, Dog Walking

"Kenzi is always our first choice when we are booking a dog sitter or walker. They are punctual, loyal, generous, communicative about availability, and spoil ... (more)"

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11. Lindsey

Student - loves playing and walking

Loop, Chicago, IL, 60601

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

"11/10 - Lindsey is a dog lover through and through. She is responsible, thoughtful and communicative. My dogs love her and I have always been able to rely on... (more)"

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12. John

Attentive + caring dog walker

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting

"John has been my go to guy when it comes to watching my dog Wilson. John has watched Wilson on several occasions and is always on time and ready to play. Wi... (more)"

Confirmed availability
This weekend
13. Britney

I love animals and they love me!

Loop, Chicago, IL, 60605

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

"Britney did an excellent job with Thor. He takes a lot of patience and she had it to give. She was also very good at sending us updates regularly. I highly r... (more)"

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14. Katie

Long walks and warm cuddles

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Katie was very responsive to messages and sent lots of cute pictures of my dog and cat! Squid seemed stoked when I came home and the house was as we left it.... (more)"

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15. Jenna

Full-time student & dog lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

"We are delighted to recommend Jenna for a dog care position. We met her through her mother, who is one of my wife’s closest friends. Jenna is a caring, hones... (more)"

Confirmed availability
Christmas and New Year
16. Chenika

Fun & Passionate Sitter!

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits

"I can't stop giving Chenika 5 stars! She is so sweet and I know I'm leaving my dog with the same love and care I would provide if I were there! She's the best! (more)"

17. Summer

Fun-Loving & Energetic Animal Lover

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Summer Hofford is a very caring and loving person. She took 2 foster cats into her home last year and took great care of them until they found permanent hom... (more)"

18. Sandra

Full time dog lover!

Lower West Side, Chicgao, IL, 60608

House Sitting

"Sandra is absolutely amazing. She's incredibly knowledgeable about dogs and their needs, and she really bonded with my dog Babs when she started at my house ... (more)"

Confirmed availability
This weekend
19. Nick

Wide open Schedule

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits

"Nick A. has been a caring and reliable pet sitter/dog walker for us for several years. He is willing to go the "extra" mile if asked. We had senior dogs at ... (more)"

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20. Hailey

I catch the eyes of your dogs!

Lower West Side, Chicago, IL, 60608

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

"Hailey took care of our dog and bird in our home over a long Thanksgiving weekend. She was great! Our pets were well-cared-for, she sent frequent pictures an... (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.