House Sitting in Armour Square, Chicago

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

1. Theresa

Dog trainer in training

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

About: I have been around dogs my entire life so I know all of the tricks that they love to pull. Not only have I had dogs my whole life, I am currently p... (more)

2. Breana

Dogs are my favorite people.

Hyde Park, Chicago, IL, 60615

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

"Breana will be the perfect fit as your dog sitter. She is responsible, hardworking, and organized. Breana has grown up with dogs and she certainly knows what... (more)"

3. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Another great sleepover for Sassy with Crystal! We called last minute for an unexpected trip and as usual, she came through for us and was exceptional. On ... (more)"

4. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"This was our first time hiring a pet sitter and Catherine was amazing! Both animals were well taken care and we could not be more pleased! Will definitely be... (more)"

5. Jac

Loving and Experienced Pet Sitter

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Jac did a Sunday to Wednesday home stay with Claudia. I appreciate the quick texts and pictures, thank you! I would recommend Jac to anyone and will certainl... (more)"

6. Sabrina

Loving life, but loving dogs more!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sabrina was amazing with Shadow from the first moment. Although Shadow can be a little hyper at times, Sabrina completely put him at ease. I came home to a h... (more)"

7. Sarah

Will show your pup so much love!!!!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah is a loving, enthusiastic dog caregiver who I have trusted with my beloved French Bulldog, Pablo several times in the past. She is very responsible an... (more)"

8. 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)"

9. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 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)"

10. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

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

5 repeat clients

"Penelope has fast become our go-to dog sitter. She has a great, patient, calming approach with dogs that is especially important with little, skittish ones,... (more)"

11. Hailey

I catch the eyes of your dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Hailey was great! I trusted leaving Tula with her for a few days over the holiday weekend. She gave me updates, sent me a pic, and my house looked untouched... (more)"

12. Aasha

I'm a dog loving recent graduate!

Near West Side, Chicago , IL, 60661

House Sitting, Drop-In Visits, Dog Walking

"Aasha is genuinely an animal lover. Her love for animals is unconditional. She easily bonds with animals. In the past, Aasha has offered excellent customer s... (more)"

13. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Krystina was such a great sitter! She was flexible in coming over to meet me and June beforehand, and checked in several times throughout the weekend with te... (more)"

14. Emily

Graduate student and dog lover

Near West Side, Chicago , IL, 60607

House Sitting

"Emily was pretty great with our long-haired dachshund puppy Blu! She would check in on him, play with him, and take him on walks while my boyfriend and I wer... (more)"

15. Eliana

Dream big and love dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Eliana took good care of our dog and cat while she stayed in our home for an extended week trip. She provided timely updates when I inquired about them throu... (more)"

16. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

"Brittany was so so great! She was extremely flexible, quick to respond, and kept me updated throughout Royal's stay with her. It was clear Brittany was very ... (more)"

17. 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)"

18. Samantha

Life is ruff! Let me make it easier

Loop, Chicago, IL, 60605

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

1 repeat client

"Samantha was amazing. We needed someone to sit with Apollo at the last minute and she came through! Apollo loved her and had so much fun playing and sleepin... (more)"

19. Rory

I love and appreciate all pups

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Rory was fantastic and was my first sitter via Rover. She took a last minute job with me (same day for a 3 day long overnight) and was great! I was comfortab... (more)"

20. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

About: Dogs & I: Over the course of my life I have raised several different dog breeds and currently still take care of my 11 year old peek-a-poo, Isabel... (more)

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

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.

Want to be added to this list of sitters in Chicago? Become a pet sitter or dog walker on Rover.

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.