House Sitting in Grand Boulevard, 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. 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)"

2. Jamie

Med Student West Loop Pooch Sitter

Near West Side, Chicago, IL, 60612

House Sitting

9 repeat clients

About: Hello! I'm Jamie, a fourth year medical student who is crazy about dogs. I grew up with/was raised by a goofy lab and an energetic corgi and have a... (more)

3. Janet

Experienced Emergency Vet Assistant

Gage Park, Chicago, IL, 60632

House Sitting, Drop-In Visits, Dog Walking

About: My name is Janet, and I am a hopeful, future vet student. When I'm not in school, or working, I am loving on any fur baby that I come across. I h... (more)

4. 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)"

5. 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 was amazing! We met for a meet and greet a few weeks before we left for the week. She made sure she knew all she needed to know about Rue during that t... (more)"

6. 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)"

7. 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)"

8. 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)"

9. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"I could not have asked for a better sitter than Crystal. She came over prior to the start of service to meet my dog and I could tell at once that she was tru... (more)"

10. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

17 repeat clients

"Penelope was amazing! Terrific communication throughout her stay and even sent tons of pictures of our little pup. Our dachshund does not like to walk withou... (more)"

11. 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)"

12. Kate

Experienced Dog Lover!!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"I have known Kate for the past 3 years. I have always admired the love and care she gives to her dog, Marshie, and any animal she comes across. Kate is a ver... (more)"

13. 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)"

14. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits

1 repeat client

"Emily was great. She picked our dog up early to help us with our travel arrangements, she sent lots of photo updates and checked in frequently. I felt like m... (more)"

15. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Emma was amazing. We had gone away the previous weekend and left our dog, Lucy, an 8-year-old Lhasa-Pomeranian mix, with friends she didn't know very well --... (more)"

Available this weekend
16. Jillian

Time with a dog is time well spent.

Lower West Side, Chicago , IL, 60608

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Jillian was super great. She was able to help me out for a last-minute trip and kept me up-to-date with photos and messages regarding my dog. (more)"

17. 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)"

18. 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)"

19. Ida

A home away from home

Bridgeport, Chicago, IL, 60609

Dog Boarding, House Sitting

3 repeat clients

"Ida responded to my post on the internet very quickly and professionally when I needed a last minute dog-sitter. Ida agreed to take care of my sweet old corg... (more)"

20. Tommy

Home full time, love dogs :)

New City, Chicago, IL, 60609

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

"Tommy LOVES dogs.He can't walk by one without saying high and going in for a pet. He is a fourth year student at the University of Michigan and is... (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.