House Sitting in Armour Square, Chicago

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

1. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Ashleigh was great. She sent lots of pictures. When we got back home Oberon was actually tired, which never happens, so she walked and played with him tons. (more)"

2. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

5 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)"

3. Aasha

I'm a dog loving recent graduate!

Near West Side, Chicago , IL, 60661

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"This was our first time using Rover. I carefully looked over all the profiles and came across Aasha. She didn't have many reviews, but I was drawn to her f... (more)"

4. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Collin is my first experience with Rover and I couldn't be more pleased. Using Rover came with short notice and I worried that would create a problem. Coll... (more)"

5. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Crystals was great. Very responsive when communicating. Very reliable and professional. And Sassy loved her! We hate to leave town, but it's nice to know tha... (more)"

6. Sidney

Experienced & Active Dog Enthusiast

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sidney was great with our dog! She was able to come last minute and kept him happy! She even came with some treats for him. We will reach out to her again. (more)"

7. Samantha

Life is ruff! Let me make it easier

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Samantha did a very good job. She was both responsive and responsible. I will definitely use her again. Collins Was happy and healthy when I returned home... (more)"

8. Emily

Graduate student and dog lover

Near West Side, Chicago , IL, 60607

House Sitting

"Emily was great! She stayed at our house while watching our dog. She is very responsible, reliable and neat. She sent pictures of our dog everyday and is a g... (more)"

9. Edilberto

Passionate Pet Care Provider

Loop, Chicago, IL, 60604

House Sitting, Drop-In Visits, Dog Walking

2 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)"

10. 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)"

11. Eliana

Dream big and love dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Eliana was a huge help in watching Grey last minute after our original sitter fell through. She showed up early to our place and met with Grey. She responded... (more)"

12. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

16 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)"

13. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

3 repeat clients

"We LOVE Brittany! She took care of Miko with a lot of love and care while were out on a 14 day trip. She stayed in our house, took care of Miko and our home.... (more)"

14. Jac

Loving and Experienced Pet Sitter

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"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)"

15. Christina

Calm, warm hearted dog lover

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Christina took excellent care of my pup while I was away for a long weekend. She communicated regularly and handled small requests, no problem! Will definite... (more)"

16. LoLo

i'm a retired High School teacher.

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Lo Lo took care of my dog, Biggie, a 39lb english bulldog for a Mon-Wed and he seemed more at eased when i got back from my work trip then when I drop him of... (more)"

17. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Krystina and Bacon (our furry kid) instantly bonded! This was our first time using Rover and Krystina was very helpful and met with us right away to ease any... (more)"

Available this weekend
18. Allison

Certified Veterinary Technician

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits

3 repeat clients

"Allison is hands down the best pet sitter! We had her stay in our home over a long weekend with our two senior pups. She provided excellent communication and... (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. Ida

A home away from home

Bridgeport, Chicago, IL, 60609

Dog Boarding, House Sitting

2 repeat clients

"Ida responded to my post on the internet very quickly and professionally when I needed a last minute dog-sitter. Ida agreed to take care of my sweet old corg... (more)"

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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.