House Sitting in Oakland, 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 did a great job with our puppy and with keeping me updated throughout the day with photos and texting. Our pup seemed happy to spend the day with her;... (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. 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)"

5. Sidney

Experienced & Active Dog Enthusiast

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Sidney was fantastic, provided me photos daily of Roro, and she was responsive and alerted me to issues. I hope to work with Sidney in the future and would r... (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

"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)"

8. 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)"

Available this weekend
9. Heon Ki

I will run with you dog

Loop, Chicago, IL, 60601

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

"Hyun Ki has always been an animal lover and is a very reliable person. He took care of my dog for 2 weeks while I was away and I can confidently recommend hi... (more)"

10. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

About: Hi there, I'm Karolina! I'm a student at DePaul and have lived with dogs for my entire life. Part of why I decided to become a dog sitter is the fa... (more)

11. 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)"

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)"

13. 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)"

14. 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)"

15. Alexandra

Loving sitter in the city.

Bridgeport, Chgo, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

18 repeat clients

"Lexy was fantastic! I felt confident leaving Reese in her care when visiting family in Colorado for 3 nights. She was easy to get in touch with and kept me u... (more)"

16. Silvia

Vegetarian/Animal lover/Writer

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Silvia, was awesome! Communication was easy and effective. Plus her experience working at PAWs really made me feel comfortable leaving my 90 lbs, energetic, ... (more)"

17. 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)"

18. 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)"

19. 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)"

20. 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)"

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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.