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.
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1. Sandra

Welcome to the bark side.

Near West Side, Chicago, IL, 60612

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

"Compassionate animal and people lover, mature way beyond her age, intelligent, artistic, punctual, clean and dependable young lady. I highly recommend her ... (more)"

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2. Laura

Love, care and joy for your dog(s)

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Laura was amazing! Her professionalism and quality care of our little Henry once again put us at ease. Thanks for being so responsive & accommodating on such... (more)"

Confirmed availability
Labor Day
3. Alice

Home full time for your dog(s) solo

Near South Side, Chicago, IL, 60616

Dog Boarding, House Sitting, Doggy Day Care

"We could not have asked for a better experience with Alice. Our dog was extremely anxious and took a while to calm down once we left her home. She kept us up... (more)"

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4. Megan

Last minute bookings available!

Armour Square, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Megan did a fantastic job watching my dogs, Muffin and Newman, for over a week at my house. they can be little terrors and she handled it wonderfully and lo... (more)"

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5. Kiana

Wags While You're Away

Bridgeport, Chicago, IL, 60616

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

"Kiana was a pleasure to have house sit for my Doberman. She spent plenty of time hanging out with him and taking him out to play and exercise. Even when unf... (more)"

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6. Shay

Love Them Like My Own

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

"Shay did an awesome job with Moksie! She's friendly, flexible and Moksie is a big fan. Her updates are great and I enjoyed the pictures she sent. Will def ... (more)"

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7. Chelsea

Available all day all summer!

Lower West Side, Pilsen, IL, 60608

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

"Chelsea LOVES dogs! I promise that you will not find another person who will care for your dog like Chelsea does. She cares for my dogs on the regular and I ... (more)"

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8. Imani

Dogs are friends not food!

Lower West Side, CHICAGO, IL, 60608

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

"Imani took great care of our pup while we were out of the country for a few days. It was nice to know she was in good hands- it really put us at ease and all... (more)"

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9. Sabrina

Loving life, but loving dogs more!

Near West Side, Chicago, IL, 60608

Dog Boarding, House Sitting

"Sabrina stayed in our home and watched our energetic husky/shepherd mix, Buckley. She did a fantastic job! Buckley seemed very happy and well cared-for whe... (more)"

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10. Breanna

Lots of love & good pictures!

Near North Side, Chicago, IL, 60611

House Sitting, Drop-In Visits, Dog Walking

"Breanna was amazing, best pup sitter and would highly recommend her for your dog! Breanna stayed in my guest bedroom while I was OOT and updated me frequentl... (more)"

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11. 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)"

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12. Ariel

Caretaker for your furry friend(s)!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Ariel is my favorite and go-to sitter. She understands my need for updates and is great with Henry. She is helpful and respectful while staying at my house. ... (more)"

Confirmed availability
Labor Day
13. Kaitlyn

I'll care for your animal as my own

Loop, Chicago, IL, 60601

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

About: I love spending time outside and at the parks. I grew up with two labs in my house and have enjoyed every second of it! Even including the unexpect... (more)

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14. Kara

Home full time - large fenced yard

Near North Side, Chicago, IL, 60654

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

About: Hi, my name is Kara! I am 27 years old and I’m currently back in school during weekday nights with plenty of time during the day and on the weekend... (more)

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15. Edilberto

Passionate Pet Care Provider

Loop, Chicago, IL, 60604

House Sitting, Drop-In Visits, Dog Walking

"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)"

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16. Alli

Home full-time

Loop, Chicago, IL, 60601

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

"The dogs were very happy and healthy when we got back from our trip. Alli was awesome and would happily recommend her. (more)"

Confirmed availability
Labor Day
17. Jaureese

Giving dogs the love they deserve

Loop, Chicago, IL, 60605

Dog Boarding, House Sitting

About: In college I cared for my Huskie for 3 years, which required an excessive amount of attention. It's no secret that they are a high maintenance bree... (more)

18. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"She was very quick to respond to my reservation request, and fortunately, was available for the days we needed. She was very communicative and sent several p... (more)"

19. Lauren

Any and all dogs!

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Lauren was wonderful! Lola loved her, and we loved receiving the daily updates and pictures while we were away. Once we returned, our place was clean and we ... (more)"

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20. Megan

Petsitter looking for new clients!

Loop, chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

About: Hi! I used to walk dogs for a dog walking company, but now just freelance petsit on Rover. I am pet first aid certified and absolutely love animals... (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.