House Sitting in Oakland, Chicago

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

1. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Karolina was such a great over night sitter for our dog Forrest while we went on a long weekend vacation. I did not have to worry one bit about our dog while... (more)"

2. Sofia

Grad student and dog lover.

Lower West Side, Chicago, IL, 60608

House Sitting

2 repeat clients

"Sofia responded quickly to messages and even sent a few photos--would highly recommend and hopefully will use her again in the future! (more)"

3. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Collin is very friendly. Pippi definitely enjoyed him staying with her. Collin took her out for two walks. He sent text updates with photos and details of wh... (more)"

Available this weekend
4. Alexandria

Pup Adventures with Alex

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

14 repeat clients

"We have two dogs: a pit mix and a French bulldog. Alex did a great job caring for our furry family and home. The girls looked nonplused when we arrived home ... (more)"

5. Charlotte

I'll treat your pet as family!

McKinley Park, Chicago, IL, 60609

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

"Charlotte was amazing with our puppy. She even trimmed her nails as she is a vet tech. (more)"

6. Edilberto

Passionate Pet Care Provider

Loop, Chicago, IL, 60604

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Edilberto was great with Shadow from the first moment. We found a really happy dog when we returned. Edilberto was also really accomodating with out late hou... (more)"

7. Robert

All furry friends welcome!

Loop, Chicago, IL, 60601

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

27 repeat clients

"My normal sitter bailed. Complete last min book Robert rocks! I was able to drop off within the hour. Deff be using again, thanks for being flexible. (more)"

8. Rachel

College student loves dogs!

Douglas, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Cooper's a lot of work - he needs a lot of attention and playtime, and Rachel was great with him! Will definitely reach out to Rachel the next time I'm in to... (more)"

9. Angie

Love & care that comes right to you

Near West Side, Chicago, IL, 60607

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

2 repeat clients

"Angie is great! She sat my pug for 7 days. She took him to her home, and also stayed in mine. She is very flexible! Also I was stuck in Florida due to the ... (more)"

10. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Krystina was so great, I almost hate her. My pup tends to attach herself to me, so seeing all these pictures of her so happy, she clearly didn't miss me at a... (more)"

11. Natalie

Loop Living and Pup Loving!

Loop, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

"Natalie was absolutly great with my boy Nookie! She works with him as if he was her own. My dog absolutly loved her and cant wait to have her over again. (more)"

12. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

2 repeat clients

"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)"

13. Mikayla

Energetic dog-lover

Woodlawn, Chicago, IL, 60637

House Sitting, Dog Walking

1 repeat client

"Mikayla was great. Sparky had lots of fun with her, we could tell. Mikayla shared pictures which we appreciated. We will use Mikayla again. (more)"

14. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

21 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)"

15. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

18 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)"

16. Audrey

Dogs are my life!

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Audrey was awesome with my two boys. She took the time to come meet me and them before scheduling her stay. She asked really great questions and cared a lot ... (more)"

17. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Crystal is the best pet momma I can imagine! Our very finicky dog jumped into her lap on her first visit with him. You know that dogs know a good person and ... (more)"

18. Allison

Certified Veterinary Technician

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits

5 repeat clients

"Allison was an excellent sitter. She was very responsive, proactive, and dependable. She also handled 2 difficult dogs very well. Would highly recommend her ... (more)"

19. Colleen

Social Work Student with Wide Avail

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

1 repeat client
No Reviews Yet

About: I've lived with different dogs for 20 years of my life, helped train many family members' pets, and dog sat for many different types and sizes of d... (more)

20. Martineja

Your dog's new best friend!

Kenwood, Chicago, IL, 60653

Dog Boarding, House Sitting, Doggy Day Care

9 repeat clients

"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)"

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Learn About Premier

With over 140,000 pet and house sitters on Rover.com, you can easily find house sitting near you.

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 eviews from pet owners who have used Rover.