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House Sitting In Near South Side 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.
1. Ariel

Caretaker for your furry friend(s)!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Ariel stayed with my two pups for the weekend and she was awesome! I left a ridiculous amount of notes and instructions and she followed everything without a... (more)"

2. 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)"

3. Margot

Keeping those tails wagging!

Kenwood, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Margot did a wonderful job watching my somewhat high maintenance senior dog, Walle. Walle has special needs including scheduled medications, as needed medica... (more)"

4. Morgan

I love dogs & dogs love me!

Lower West Side, Chicago, IL, 60608

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

"I would highly recommend Morgan as she has taken care of my dog on several occasions and he just adores her. She treats your dog as if they were her own givi... (more)"

5. Rachel

No longer accepting work!

Douglas, Chicago, IL, 60609

House Sitting

"Rachel took care of Zigz in my apartment for the better part of a week. Rachel was quick to respond and took great care of Zigz. I got detailed messages and ... (more)"

6. Tara

Care for your dog like my own

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Tara was fantastic and went above and beyond expectations. She sent many updates and pictures/videos. My dog went on adventures w/ her, and seemed quite happ... (more)"

7. Hailey

Experienced ASPCA volunteer!!

Loop, Chicago, IL, 60601

House Sitting, Drop-In Visits, Dog Walking

"Hailey did a great job with my Dogs. And even gave special attention to my puppy, because he’s still in the training stages. Thanks for taking my last minute... (more)"

8. Edilberto

Passionate Pet Care Provider

Loop, Chicago, IL, 60604

House Sitting, Drop-In Visits, Dog Walking

"Eddie was an amazing sitter and is a great all around guy. Was super flexible when my flight out of town had some hiccups. My pups loved him, too! (more)"

Confirmed 4th of July Availability
9. Kenni

I'll Run With Your Dog

Lower West Side, Chicago, IL, 60608

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)"

10. Tana

Loving care when you are not there

Loop, Chicago, IL, 60601

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

"Tana did a fantastic job watching our two dogs, and was easy to communicate with. She took them to the local park, and took our younger, more spry dog on a v... (more)"

11. Julio

Let’s go have a PAWesome time!

Near West Side, CHICAGO, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

"Julio was wonderful and super flexible with my schedule. I appreciated the pictures and updates he sent. My dog had a great time and I would be happy to book... (more)"

12. Blake

I'll treat your dog like royalty

Near West Side, Chicago, IL, 60661

House Sitting, Drop-In Visits, Dog Walking

"Blake was AMAZING! My dog sitter last minute cancelled on me and within a few minutes Blake responded and was able to watch my dog for a couple of days. He t... (more)"

13. Kelyn

The Dawg Whisperer!

Near North Side, Chicago, IL, 60611

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

"Kelyn is an amazing dog-sitter. He's caring, responsible, and always very attentive to pets. He thoroughly enjoyed playing with my dog and made sure he got h... (more)"

14. Maria

Dog's needs come first

Loop, Chicago, IL, 60603

House Sitting, Drop-In Visits

"Maria was great! She came for a few hours each day to play with our puppy. Because he's not yet fully vaccinated, he's not able to go to daycare or on walk... (more)"

15. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Karolina was amazing! We had some totally unexpected and very annoying apartment maintenance work done during Karolina's stay-- our floors had to be almost c... (more)"

16. Madeleine

Caring for dogs is my happy place!

Near North Side, Chicago, IL, 60611

House Sitting, Drop-In Visits, Dog Walking

"Madeleine was wonderful! She sent updates and photos of Zara while she stayed the weekend to watch her. She was very sweet and attentive. I appreciate the gr... (more)"

17. Libby

I love dogs and dogs love me!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Libby is one of the most caring people I know! She puts in extra effort to show her loved ones that she cares about them and I have no doubt she would do the... (more)"

18. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Krystina was amazing. I don't think my dog missed me a bit as she seemed so loved when I got home. Krystina even gave Sophie a bath when I was gone because S... (more)"

19. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"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)"

20. Emily

Downtown dog sitter.

Loop, Chicago, IL, 60605

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

"Emily would be a good dog sitter - we have a Pekingese dog (he's now 12 years old) and for a few years I was ill and unable to care of Frodo(his name) and E... (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.