House Sitting in Oakland, Chicago

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

1. Imani

Dogs are friends not food!

Lower West Side, CHICAGO, IL, 60608

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

"Imani exceeded expectations. Marlowe was indeed sad to see her go. She was extremely attentive to Marlowe's needs and went above and beyond. This was the lon... (more)"

2. TIANJIAO

Ariel's Dog Haven

Kenwood, CHICAGO, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care

"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)"

3. Allison

Certified Veterinary Technician

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits

"Allison is a fantastic sitter! She stayed overnight with our lab-shepherd mix, Luna, while we were out of town for a wedding. She was communicative throughou... (more)"

4. Ariel

Caretaker for your furry friend(s)!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Faith (our puppy), loved having Ariel babysit her. She enjoyed her walks and chill time with Ariel. We (Faith's Mom & Dad) appreciated receiving frequent upd... (more)"

5. Edilberto

Passionate Pet Care Provider

Loop, Chicago, IL, 60604

House Sitting, Drop-In Visits, Dog Walking

"Eddie did a home stay with Claudia for a week and was a big help. He provided daily updates, very responsive, flexible, and knowledgeable. Claudia has separa... (more)"

6. Payal

West Town Pet Sitter

McKinley Park, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Payal was better than I could have asked for. We just had our 10 week old puppy come home with us the other day, she was so scared. I dropped my puppy off at... (more)"

7. Rachel

No longer accepting work!

Douglas, Chicago, IL, 60609

House Sitting

"Rachel was great to work with. Rachel stayed at my house for the weekend and took very good care of Chloe. She very responsive when I had questions. She was ... (more)"

Available this weekend
8. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting

"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)"

9. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Harper loves hanging out with Karolina! She is so amazing and helped us even with a weird schedule (switching off between house sitters while we were on an e... (more)"

10. Debra

Flexible schedule-will run with dog

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"I have used Debra's services on 2 different occasions so far. She's been great! She's reliable and communicates with me to let me know the animals are doing ... (more)"

11. Nina

Student & home often, love to run!

Hyde Park, Chicago, IL, 60637

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

"Nina has cared for our beloved Dobby multiple times. He is always so excited when we drop him off! I appreciate that Nina sends me lots of photos of the fun ... (more)"

12. Jenisa

Pet Lover- Home Full Time

South Side, Chicago, IL, 60653

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

"Jenisa has a natural way with dogs. They seem to love her instantly. She has cared for my small dogs and my parents large dog for a few years now. Jenisa cl... (more)"

13. Alex

I'll take your dog for a run

Kenwood, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"It is clear that a Alex loves animals and he is very responsible taking care of them. We have a dog and a cat that he has taken care of them for years when n... (more)"

14. Kat

Recent grad who LOVES DOGS

Kenwood, Chicago, IL, 60615

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

About: Hi! I'm Kat. I am a 22 year old biologist, and I just graduated from BU in Boston and accepted a job at the University of Chicago. My building is p... (more)

15. Andrea

Fun times waiting to be had!

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"My husband and I along with Buster visited your fair city last Monday June 15 when the flood gates opened. We asked Andrea to look after Buster at our hotel... (more)"

Available this weekend
16. Kenni

I'll Run With Your Dog

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Kenni is a great fur mom. They have been to puppy training class and uses those lessons daily! They are very respectful of your commands and rules for your d... (more)"

17. Puck

Long walks and runs for active dogs

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Puck is a responsible and communicative dog caregiver. They took care of dog, Sasha, when my family was on vacation, and went above and beyond to make sure s... (more)"

18. Enoch

Rover Sitter/Boarder ~SINCE 2015!

Bridgeport, Chicago, IL, 60608

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

"I hope I can put into words how wonderful Enoch was. We have three dogs and have never left them for a long period of time with anyone but family. I was a ne... (more)"

19. Katlyn

Consistent & Loving :)

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Katlyn was great, coming to meet Blue before our trip. Blue loved her and we felt comfortable leaving her to go on our trip. She was very respectful of our a... (more)"

20. Andrea

Dogs love my peaceful personality!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Andrea is a very loving and responsible caretaker! She really pays attention to what your animal companion needs and treats them like one of her own. I defin... (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.