House Sitting in Kenwood, 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. Jac

loving and experienced pet sitter

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Jac looked after my sweet corgi, Oliver, while I went away for a weekend. She took amazing care of him! She even sent little pictures of them having fun toge... (more)"

Confirmed New Years Availability
2. Daniela

Reliable & Experienced Sitter

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Daniela is the best!! I have a 60 lbs Plott Hound and left to go out of the country for three weeks during which time Daniela stayed at my house. I came home... (more)"

3. Holly

Dog lover 1st, law student 2nd!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Holly went way above and beyond being a good sitter- she was fantastic! She was always prompt, friendly and professional. We received pictures and updates th... (more)"

4. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

"Our experience with LeAnna was wonderful! She took perfect care of our dog and cat and kept us updated throughout the stay. She really listened and We are co... (more)"

Available this weekend
5. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"I highly recommend Emma. Our household is big and crazy and she held her own :-) She sent lots of pictures and updates so we didn't have to worry about our k... (more)"

6. Sabrina

Loving life, but loving dogs more!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I grew up with two dogs, a Doberman and a mixed breed, and I am very comfortable and experienced around all types of dogs and all types of dog pers... (more)

7. Hailey

I catch the eyes of your dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Hailey took care of our dog and bird in our home over a long Thanksgiving weekend. She was great! Our pets were well-cared-for, she sent frequent pictures an... (more)"

Available this weekend
8. 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)"

9. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits

1 repeat client

"Emily was great. She picked our dog up early to help us with our travel arrangements, she sent lots of photo updates and checked in frequently. I felt like m... (more)"

10. Silvia

Vegetarian/Animal lover/Writer

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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. Erin

Run And Play All Day!

Lower West Side, Chicago, IL, 60608

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

1 repeat client

"Erin is an excellent sitter! She's very clearly an animal lover, and I feel completely at peace when I leave Rumi with her. (more)"

12. Megan

grad student & dog lover!

Hyde Park, Chicago , IL, 60615

House Sitting, Dog Walking

1 repeat client

"Carter absolutely loved Megan! She enjoyed her company and made a new friend. We'd definitely have Megan watch Carter for us again! (more)"

Confirmed Holiday Availability
13. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

"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)"

Confirmed Holiday Availability
14. Myk'La

Energetic, artsy, happy and caring

Chatham, Chicago, IL, 60619

House Sitting, Drop-In Visits, Dog Walking

"Myk'La is a awesome person and some one i'd highly recommended for the Dog Caregiver position.She posess a high spirit personality along with an outgoing and... (more)"

15. Christina

Calm, warm hearted dog lover

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 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. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"I can't recommend Collin highly enough! He's kind, patient, responsible and very good with dogs. He really takes the time to know what your pet needs and how... (more)"

17. 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)"

18. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

" Mindy is a loving and effective dog owner. The passion she has for taking care of her dogs and herself is exceptional. She is one of the most intelligent pe... (more)"

Confirmed Holiday Availability
19. Enoch

All dogs/cats/pets welcomed!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits

7 repeat clients

"Enoch was very patient and full of energy! He takes a lot of pictures and I felt super comfortable leaving my animals with him. He communicated daily with me... (more)"

Confirmed Holiday Availability
20. Leolin

Responsible animal lover!!

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"I've known Leolin for 10 years and can attest to her love for animals. She is a vegan, which is something that is very important to her and reflects the resp... (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.